Molecules

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Open AccessArticle

In Vitro Antioxidant Activity and Hepatoprotective Effects of Lentinula edodes against Paracetamol-Induced Hepatotoxicity

by Sreenivasan Sasidharan, Sugumaran Aravindran, Lachimanan Yoga Latha, Ratnasamy Vijenthi, Dharmaraj Saravanan and Santhanam Amutha

Molecules 2010, 15(6), 4478-4489; https://doi.org/10.3390/molecules15064478 - 23 Jun 2010

Cited by 58 | Viewed by 12482

Abstract

Background: The objective of this study was to investigate the antioxidant and hepatoprotective effects of methanolic extracts of L. edodes and the determination of their total phenolics content. Results: The amount of total phenolics was estimated to be 70.83 mg Gallic [...] Read more.

Background: The objective of this study was to investigate the antioxidant and hepatoprotective effects of methanolic extracts of L. edodes and the determination of their total phenolics content. Results: The amount of total phenolics was estimated to be 70.83 mg Gallic Acid Equivalent (GAE) per gram of dry extract. The antioxidant activity of the L. edodes extract was 39.0% at a concentration of 1 mg/mL and was also concentration dependant, with an EC₅₀ value of 4.4 mg/mL. Different groups of animals (Wister albino mice) were administered paracetamol (1 g/kg, p.o.). L. edodes extract at a dose of 200 mg/kg was administered to the paracetamol treated mice for seven days. The effects of L. edodes extract on serum transaminases (SGOT, SGPT), alkaline phosphatase (ALP) and bilirubin were measured in the paracetamol-induced hepatotoxic mice. L. edodes extract produced significant (p < 0.05) hepatoprotective effects by decreasing the activity of serum enzymes and bilirubin. Conclusions: From these results, it was suggested that L. edodes extract could perhaps protect liver cells from paracetamol-induced liver damage by its antioxidative effect on hepatocytes, hence diminishing or eliminating the harmful effects of toxic metabolites of paracetamol. Full article

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Open AccessArticle

Antioxidant Properties of European Cranberrybush Fruit (Viburnum opulus var. edule)

by Otakar Rop, Vojtech Reznicek, Magdalena Valsikova, Tunde Jurikova, Jiri Mlcek and Daniela Kramarova

Molecules 2010, 15(6), 4467-4477; https://doi.org/10.3390/molecules15064467 - 23 Jun 2010

Cited by 81 | Viewed by 17373

Abstract

In the literature there is little available information concerning European cranberrybush fruit (Viburnum opulus var. edule). This plant can be cultivated, even in harsh climatic conditions, because of its low environmental demands, and it is possible to harvest the fruit even [...] Read more.

In the literature there is little available information concerning European cranberrybush fruit (Viburnum opulus var. edule). This plant can be cultivated, even in harsh climatic conditions, because of its low environmental demands, and it is possible to harvest the fruit even in the snow cover. The aim of this study was to determine the content of polyphenolics, antioxidant activity, flavonoids and vitamin C in the fruit of three cultivars ´Leningradskaya otbornaya´, ´Souzga´ and ´Taezny rubiny´ of this species. In the case of polyphenolics, high contents [up to 8.29 g of gallic acid/kg of fresh mass (FM)] were observed. The 1,1´-diphenyl-2-picrylhydrazyl (DPPH) and 2,2´-azinobis-3-ethyl-benzthiazino-6-sulphonic acid (ABTS) tests were applied to determine antioxidant activity, which was also high in comparison with other fruit species. The corresponding correlations between the polyphenolic content and antioxidant activity were in case of the DPPH test r² = 0.88 and for the ABTS test r² = 0.98. For comparison, the scavenging activity towards reactive oxygen species (superoxide anion, hydroxyl radical and nitric oxide) was determined by using a 25% fruit extract of particular cultivars. Antioxidant efficiency was also assessed using the rat liver slice model. Furthermore, the contents of flavonoids and vitamin C were assayed, giving values of 4.89 g/kg and 1.64 g/kg FM, respectively. The work should contribute to the popularization of this species as a promising crop plant in human nutrition. Full article

(This article belongs to the Special Issue Antioxidants)

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Open AccessArticle

HPLC and Anti-Inflammatory Studies of the Flavonoid Rich Chloroform Extract Fraction of Orthosiphon Stamineus Leaves

by Mun Fei Yam, Vuanghao Lim, Ibrahim Muhammad Salman, Omar Ziad Ameer, Lee Fung Ang, Noersal Rosidah, Muthanna Fawzy Abdulkarim, Ghassan Zuhair Abdullah, Rusliza Basir, Amirin Sadikun and Mohd Zaini Asmawi

Molecules 2010, 15(6), 4452-4466; https://doi.org/10.3390/molecules15064452 - 21 Jun 2010

Cited by 75 | Viewed by 16631

Abstract

The aim of the present study was to verify the anti-inflammatory activity of Orthosiphon stamineus leaf extracts and to identify the active compound(s) contributing to its anti-inflammatory activity using a developed HPLC method. Active chloroform extract of O. stamineus was fractionated into three [...] Read more.

The aim of the present study was to verify the anti-inflammatory activity of Orthosiphon stamineus leaf extracts and to identify the active compound(s) contributing to its anti-inflammatory activity using a developed HPLC method. Active chloroform extract of O. stamineus was fractionated into three fractions using a dry flash column chromatography method. These three fractions were investigated for anti-peritoneal capillary permeability, in vitro nitric oxide scavenging activity, anti-inflammatory and nitric oxide (NO) inhibition using carrageenan-induced hind paw edema method. The flavonoid rich chloroform extract fraction (CF2) [containing sinensetin (2.86% w/w), eupatorin (5.05% w/w) and 3’-hydroxy-5,6,7,4’-tetramethoxyflavone (1.101% w/w)], significantly reduced rat hind paw edema, NO and decreased dye leakage to peritoneal cavity at p < 0.05. IC₅₀ of in vitro NO scavenging of CF2 was 0.3 mg/mL. These results suggest that the anti-inflammatory properties of these CF2 may possibly be due to the presence of flavonoid compounds capable of affecting the NO pathway. Full article

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Open AccessEditorial

Continued Growth of the Impact Factors of MDPI Open Access Journals

by Dietrich Rordorf

Molecules 2010, 15(6), 4450-4451; https://doi.org/10.3390/molecules15064450 - 21 Jun 2010

Cited by 5 | Viewed by 29894

Abstract

We are pleased to report the continued increase of the Impact Factors of MDPI journals in 2009 (see Table 1 and Figure 1). As noted in a similar Editorial published in June 2009, the Impact Factors of MDPI journals have been steadily recovering [...] Read more.

We are pleased to report the continued increase of the Impact Factors of MDPI journals in 2009 (see Table 1 and Figure 1). As noted in a similar Editorial published in June 2009, the Impact Factors of MDPI journals have been steadily recovering since the inception of the full Open Access publishing policy in early 2007 [1]. We are pleased to see that all journals now have an Impact Factor much higher than 1. In 2011 the Journal Citation Report (JCR) will include the first official Impact Factor of Entropy , and in 2012, the International Journal of Environmental Research and Public Health will be included for the first time. Nevertheless, we are already able to compute a preliminary impact factor of approximately 1.4 for Entropy [2]. [...] Full article

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Open AccessArticle

The Synthesis of Glycyrrhetinic Acid Derivatives Containing A Nitrogen Heterocycle and Their Antiproliferative Effects in Human Leukemia Cells

by Yuan Gao, Xin Guo, Xiaojing Li, Dan Liu, Dandan Song, Ye Xu, Ming Sun, Yongkui Jing and Linxiang Zhao

Molecules 2010, 15(6), 4439-4449; https://doi.org/10.3390/molecules15064439 - 21 Jun 2010

Cited by 18 | Viewed by 9927

Abstract

Fifteen novel glycyrrhetinic acid derivatives containing a nitrogen heterocycle at C-30 and with different A-ring substituents were designed and synthesized. All of these derivatives have improved antiproliferative effects against human HL-60 leukemia cells. Compounds with a cyano-enone functionality on the A-ring exhibit greater [...] Read more.

Fifteen novel glycyrrhetinic acid derivatives containing a nitrogen heterocycle at C-30 and with different A-ring substituents were designed and synthesized. All of these derivatives have improved antiproliferative effects against human HL-60 leukemia cells. Compounds with a cyano-enone functionality on the A-ring exhibit greater growth inhibitory effects, compared to those with a 2-hydroxymethylene-3-keto, an isoxazole, or a 2-cyano-3-keto group. N-(2-cyano-3,11-dioxoolean-1,12-dien-30-yl)-4-piperidyl piperidine (9b) was found to be two-fold more potent than methyl 2-cyano-3,11-dioxooleana-1,12- dien-30-oate(CDODO-Me-11). Full article

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Open AccessArticle

Synthesis of 2-(2-Aminopyrimidine)-2,2-difluoroethanols as Potential Bioisosters of Salicylidene Acylhydrazides

by Markus K. Dahlgren, Christopher T. Öberg, Erika A. Wallin, Pär G. Janson and Mikael Elofsson

Molecules 2010, 15(6), 4423-4438; https://doi.org/10.3390/molecules15064423 - 21 Jun 2010

Cited by 11 | Viewed by 8349

Abstract

Salicylidene acylhydrazides are inhibitors of type III secretion in several Gram-negative pathogens. To further develop the salicylidene acylhydrazides, scaffold hopping was applied to replace the core fragment of the compounds. The novel 2-(2-amino-pyrimidine)-2,2-difluoroethanol scaffold was identified as a possible analog to the salicylidene [...] Read more.

Salicylidene acylhydrazides are inhibitors of type III secretion in several Gram-negative pathogens. To further develop the salicylidene acylhydrazides, scaffold hopping was applied to replace the core fragment of the compounds. The novel 2-(2-amino-pyrimidine)-2,2-difluoroethanol scaffold was identified as a possible analog to the salicylidene acylhydrazide core structure. The synthesis of a library of 2-(2-amino-pyrimidine)-2,2-difluoro-ethanols is described in this paper. Full article

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Open AccessArticle

Synthesis of 2- and 7- Substituted C₁₉ Steroids Having a 1,4,6-Triene or 1,4-Diene Structure and Their Cytotoxic Effects on T47D and MDA-MB231 Breast Cancer Cells

by Minwoo Kim and Eunsook Ma

Molecules 2010, 15(6), 4408-4422; https://doi.org/10.3390/molecules15064408 - 21 Jun 2010

Cited by 3 | Viewed by 7182

Abstract

2-Chloro-, 2-bromo- and 2-azido-1,4,6-androstatriene-3,17-diones were synthesized from 1α,2α-epoxy-4,6-androstadiene-3,17-dione (2) using HCl, HBr and NaN₃, respectively. Compound 2 was also reacted with NaCN to give 2-cyano-1,4,6-androstatriene-3,17-dione (5) and 2β-cyano-1α-hydroxy-4,6-androstadiene-3,17-dione (6). 6α,7α-Epoxy-1,4-androstadiene-3,17-dione (8) was reacted [...] Read more.

2-Chloro-, 2-bromo- and 2-azido-1,4,6-androstatriene-3,17-diones were synthesized from 1α,2α-epoxy-4,6-androstadiene-3,17-dione (2) using HCl, HBr and NaN₃, respectively. Compound 2 was also reacted with NaCN to give 2-cyano-1,4,6-androstatriene-3,17-dione (5) and 2β-cyano-1α-hydroxy-4,6-androstadiene-3,17-dione (6). 6α,7α-Epoxy-1,4-androstadiene-3,17-dione (8) was reacted with HCl, HBr and NaN₃ to form the corresponding 7β-chloro-, 7β-bromo- and 7β-azido-6α-hydroxy-1,4-androstadiene-3,17-diones. The cytotoxic activity of these compounds towards T47D (estrogen-dependent) and MDA-MB231 (estrogen-independent) breast cancer cell lines was evaluated. The 6α-hydroxy-7β-substituted analogs were more active than the 2-substituted analogs on both cell lines. Compound 2 showed the highest selective activity against the T47D (IC₅₀ 7.1 μM) cell line and 5 showed good cytotoxic activity on MDA-MB231 (IC₅₀ 18.5 μM) cell line, respectively. The 6α,7α-epoxy analog 8 also showed high cytotoxic activity on both cell lines (IC₅₀ 17.3 μM on T47D and IC₅₀ 26.9 μM on MDA-MB231). Full article

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Open AccessCommunication

Preparation and Physicochemical Properties of the Complex of Naringenin with Hydroxypropyl-β-Cyclodextrin

by Jiping Wen, Benguo Liu, Erdong Yuan, Yuxiang Ma and Yongyi Zhu

Molecules 2010, 15(6), 4401-4407; https://doi.org/10.3390/molecules15064401 - 18 Jun 2010

Cited by 68 | Viewed by 10901

Abstract

In this study a complex of naringenin with hydroxypropyl-β-cyclodextrin (HP-β-CD) was prepared to improve the hydrophilicity of naringenin. The physicochemical properties of the complex were analyzed by ultraviolet-visible spectrometry (UV), infrared spectrometry (IR), X-ray diffractometry (XRD), differential scanning calorimetry (DSC). The result showed [...] Read more.

In this study a complex of naringenin with hydroxypropyl-β-cyclodextrin (HP-β-CD) was prepared to improve the hydrophilicity of naringenin. The physicochemical properties of the complex were analyzed by ultraviolet-visible spectrometry (UV), infrared spectrometry (IR), X-ray diffractometry (XRD), differential scanning calorimetry (DSC). The result showed that naringenin had been molecularly dispersed in the HP-β-CD matrix, not forming a new compound and HPLC analysis showed that the solubility of naringenin in water was enhanced from 4.38 μg/mL to 1,272.31 μg/mL. Full article

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Open AccessArticle

Lead Generation and Optimization Based on Protein-Ligand Complementarity

by Koji Ogata, Tetsu Isomura, Shinji Kawata, Hiroshi Yamashita, Hideo Kubodera and Shoshana J. Wodak

Molecules 2010, 15(6), 4382-4400; https://doi.org/10.3390/molecules15064382 - 17 Jun 2010

Cited by 10 | Viewed by 9157

Abstract

This work proposes a computational procedure for structure-based lead generation and optimization, which relies on the complementarity of the protein-ligand interactions. This procedure takes as input the known structure of a protein-ligand complex. Retaining the positions of the ligand heavy atoms in the [...] Read more.

This work proposes a computational procedure for structure-based lead generation and optimization, which relies on the complementarity of the protein-ligand interactions. This procedure takes as input the known structure of a protein-ligand complex. Retaining the positions of the ligand heavy atoms in the protein binding site it designs structurally similar compounds considering all possible combinations of atomic species (N, C, O, CH_3, NH,etc). Compounds are ranked based on a score which incorporates energetic contributions evaluated using molecular mechanics force fields. This procedure was used to design new inhibitor molecules for three serine/threonine protein kinases (p38 MAP kinase, p42 MAP kinase (ERK2), and c-Jun N-terminal kinase 3 (JNK3)). For each enzyme, the calculations produce a set of potential inhibitors whose scores are in agreement with IC50 data and Ki values. Furthermore, the native ligands for each protein target, scored within the five top-ranking compounds predicted by our method, one of the top-ranking compounds predicted to inhibit JNK3 was synthesized and his inhibitory activity confirmed against ATP hydrolysis. Our computational procedure is therefore deemed to be a useful tool for generating chemically diverse molecules active against known target proteins. Full article

(This article belongs to the Special Issue Structure-Based Drug Design)

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Open AccessArticle

MALDI-TOF MS Analysis of Condensed Tannins with Potent Antioxidant Activity from the Leaf, Stem Bark and Root Bark of Acacia confusa

by Shu-Dong Wei, Hai-Chao Zhou, Yi-Ming Lin, Meng-Meng Liao and Wei-Ming Chai

Molecules 2010, 15(6), 4369-4381; https://doi.org/10.3390/molecules15064369 - 15 Jun 2010

Cited by 47 | Viewed by 12559

Abstract

The structures of the condensed tannins from leaf, stem bark and root bark of Acacia confusa were characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analysis, and their antioxidant activities were measured using 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and ferric reducing/antioxidant [...] Read more.

The structures of the condensed tannins from leaf, stem bark and root bark of Acacia confusa were characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analysis, and their antioxidant activities were measured using 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and ferric reducing/antioxidant power (FRAP) assays. The results showed that the condensed tannins from stem bark and root bark include propelargonidin and procyanidin, and the leaf condensed tannins include propelargonidin, procyanidin and prodelphinidin, all with the procyanidin dominating. The condensed tannins had different polymer chain lengths, varying from trimers to undecamers for leaf and root bark and to dodecamers for stem bark. The condensed tannins extracted from the leaf, stem bark and root bark all showed a very good DPPH radical scavenging activity and ferric reducing power. Full article

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Open AccessArticle

β-Enamino Esters in Heterocyclic Synthesis: Synthesis of Pyrazolone and Pyridinone Derivatives

by Abdellatif Mohamed Salaheldin and Mariam Abdullah Al-Sheikh

Molecules 2010, 15(6), 4359-4368; https://doi.org/10.3390/molecules15064359 - 15 Jun 2010

Cited by 14 | Viewed by 10178

Abstract

An efficient and convenient synthesis of pyrrolidinones and pyridinones utilizing enamino esters as starting material has been described. The structures of the compounds obtained were confirmed by spectral and elemental analyses. Full article

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Open AccessReview

Photochemical Oxidative Cyclisation of Stilbenes and Stilbenoids—The Mallory-Reaction

by Kåre B. Jørgensen

Molecules 2010, 15(6), 4334-4358; https://doi.org/10.3390/molecules15064334 - 14 Jun 2010

Cited by 209 | Viewed by 17648

Abstract

After Mallory described in 1964 the use of iodine as catalyst for the photochemical cyclisation of stilbenes, this reaction has proven its effectiveness in the synthesis of phenanthrenes, other PAHs and phenacenes with a surprisingly large selection of substituents. The “early age” of [...] Read more.

After Mallory described in 1964 the use of iodine as catalyst for the photochemical cyclisation of stilbenes, this reaction has proven its effectiveness in the synthesis of phenanthrenes, other PAHs and phenacenes with a surprisingly large selection of substituents. The “early age” of the reaction was reviewed by Mallory in 1984in a huge chapter in the Organic Reactions series, but the development has continued. Alternative conditions accommodate more sensitive substituents, and isomers can be favoured by sacrificial substituents. Herein the further developments and applications of this reaction after 1984 are discussed and summarized. Full article

(This article belongs to the Special Issue Photochemistry in Organic Synthesis)

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Open AccessArticle

Antioxidant Activities, Total Phenolics and Flavonoids Content in Two Varieties of Malaysia Young Ginger (Zingiber officinale Roscoe)

by Ali Ghasemzadeh, Hawa Z. E. Jaafar and Asmah Rahmat

Molecules 2010, 15(6), 4324-4333; https://doi.org/10.3390/molecules15064324 - 14 Jun 2010

Cited by 439 | Viewed by 32710

Abstract

Ginger (Zingiber officinale Roscoe) is a well known and widely used herb, especially in Asia, which contains several interesting bioactive constituents and possesses health promoting properties. In this study, the antioxidant activities of methanol extracts from the leaves, stems and rhizomes of [...] Read more.

Ginger (Zingiber officinale Roscoe) is a well known and widely used herb, especially in Asia, which contains several interesting bioactive constituents and possesses health promoting properties. In this study, the antioxidant activities of methanol extracts from the leaves, stems and rhizomes of two Zingiber officinale varieties (Halia Bentong and Halia Bara) were assessed in an effort to compare and validate the medicinal potential of the subterranean part of the young ginger. The antioxidant activity and phenolic contents of the leaves as determined by the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay and the total amounts of phenolics and flavonoids were higher than those of the rhizomes and stems. On the other hand, the ferric reducing/antioxidant potential (FRAP) activity of the rhizomes was higher than that of the leaves. At low concentration the values of the leaves’ inhibition activity in both varieties were significantly higher than or comparable to those of the young rhizomes. Halia Bara had higher antioxidant activities as well as total contents of phenolic and flavonoid in comparison with Halia Bentong. This study validated the medicinal potential of the leaves and young rhizome of Zingiber officinale (Halia Bara) and the positive relationship between total phenolics content and antioxidant activities in Zingiber officinale. Full article

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Open AccessArticle

Phytotoxic Activities of Mediterranean Essential Oils

by Luiz Fernando Rolim De Almeida, Fernando Frei, Emilia Mancini, Laura De Martino and Vincenzo De Feo

Molecules 2010, 15(6), 4309-4323; https://doi.org/10.3390/molecules15064309 - 14 Jun 2010

Cited by 140 | Viewed by 13906

Abstract

Twelve essential oils from Mediterranean aromatic plants were tested for their phytotoxic activity, at different doses, against the germination and the initial radicle growth of seeds of Raphanus sativus, Lactuca sativa and Lepidium sativum. The essential oils were obtained from Hyssopus [...] Read more.

Twelve essential oils from Mediterranean aromatic plants were tested for their phytotoxic activity, at different doses, against the germination and the initial radicle growth of seeds of Raphanus sativus, Lactuca sativa and Lepidium sativum. The essential oils were obtained from Hyssopus officinalis, Lavandula angustifolia, Majorana hortensis, Melissa officinalis, Ocimum basilicum, Origanum vulgare, Salvia officinalis and Thymus vulgaris (Lamiaceae), Verbena officinalis (Verbenaceae), Pimpinella anisum, Foeniculum vulgare and Carum carvi (Apiaceae). The germination and radicle growth of tested seeds were affected in different ways by the oils. Thyme, balm, vervain and caraway essential oils were more active against both germination and radicle elongation. Full article

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Open AccessArticle

Design of Novel 4-Hydroxy-chromene-2-one Derivatives as Antimicrobial Agents

by Milan Mladenović, Nenad Vuković, Slobodan Sukdolak and Slavica Solujić

Molecules 2010, 15(6), 4294-4308; https://doi.org/10.3390/molecules15064294 - 11 Jun 2010

Cited by 33 | Viewed by 9885

Abstract

This paper presents the design of novel 4-hydroxy-chromene-2 one derivatives, based on previously obtained minimal inhibitory concentration values (MICs), against twenty four microorganism cultures, Gram positive and negative bacteria and fungi. Two of our compounds, 3b (MIC range 130–500 μg/mL) and 9c (31.25–62.5 [...] Read more.

This paper presents the design of novel 4-hydroxy-chromene-2 one derivatives, based on previously obtained minimal inhibitory concentration values (MICs), against twenty four microorganism cultures, Gram positive and negative bacteria and fungi. Two of our compounds, 3b (MIC range 130–500 μg/mL) and 9c (31.25–62.5 μg/mL), presented high potential antimicrobial activity. The compound 9c had equal activity to the standard ketoconazole (31.25 μg/mL) against M. mucedo. Enlarged resistance of S. aureus, E. coli and C. albicans on the effect of potential drugs and known toxicity of coumarin antibiotics, motivated us to establish SAR and QSAR models of activity against these cultures and correlate biological activity, molecular descriptors and partial charges of functional groups to explain activity and use for the design of new compounds. The QSAR study presents essential relation of antimicrobial activity and dominant substituents, 4-hydroxy, 3-acetyl and thiazole functional groups, also confirmed through molecular docking. The result was ten new designed compounds with much improved predicted inhibition constants and average biological activity. Full article

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Open AccessArticle

Bisbenzamidines as Antifungal Agents. Are Both Amidine Functions Required to Observe an Anti-Pneumocystis carinii Activity?

by Julien Laurent, Dimitri Stanicki, Tien L. Huang, Eduardo Dei-Cas, Muriel Pottier, El Mouktar Aliouat and Jean Jacques Vanden Eynde

Molecules 2010, 15(6), 4283-4293; https://doi.org/10.3390/molecules15064283 - 11 Jun 2010

Cited by 11 | Viewed by 9045

Abstract

A library of 19 novel 4-(4-phenylpiperazine-1-yl)benzamidines has been synthesized and evaluated in vitro against Pneumocystis carinii. Among these compounds, N-ethyl- and N-hexyl-4-(4-phenylpiperazine-1-yl)benzamidines emerged as the most promising compounds, with inhibition percentages at 10.0 µg/mL of 87% and 96%, respectively. Those [...] Read more.

A library of 19 novel 4-(4-phenylpiperazine-1-yl)benzamidines has been synthesized and evaluated in vitro against Pneumocystis carinii. Among these compounds, N-ethyl- and N-hexyl-4-(4-phenylpiperazine-1-yl)benzamidines emerged as the most promising compounds, with inhibition percentages at 10.0 µg/mL of 87% and 96%, respectively. Those compounds remained active at 0.1 µg/mL. Full article

(This article belongs to the Special Issue ECSOC-13)

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Open AccessArticle

Synthesis and Bioactivity of N-Benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] Semicarbazide Derivatives

by Zining Cui, Yun Ling, Baoju Li, Yongqiang Li, Changhui Rui, Jingrong Cui, Yanxia Shi and Xinling Yang

Molecules 2010, 15(6), 4267-4282; https://doi.org/10.3390/molecules15064267 - 11 Jun 2010

Cited by 22 | Viewed by 9711

Abstract

In order to find novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide [...] Read more.

In order to find novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates with 5-(substituted phenyl)-2-furoyl hydrazine, and the structures were confirmed by IR, ¹H-NMR, elemental analysis and single crystal X-ray diffraction analyses (compound E2). The bioassay results indicated that the title compounds exhibit good insecticidal activity, especially towards Plutella xylostella L., but had lower fungicidal activity. Inspiringly, the title compounds possessed obvious anticancer activity against human promyelocytic leukemic cell line (HL-60), and some of the title compounds also had activity against human hepatocellular carcinoma cell line (Bel-7402), human gastric carcinoma cell line (BGC-823), and human nasopharyngeal carcinoma cell line (KB). The results indicated that the linkage in the lead compounds was important to the bioactivity and spectra. The modification on the urea linkage is an effective strategy to discover new pesticide and drug candidates. Full article

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Open AccessArticle

Synthesis of Bosutinib from 3-Methoxy-4-hydroxybenzoic Acid

by Xiao Jia Yin, Guan Hong Xu, Xu Sun, Yan Peng, Xing Ji, Ke Jiang and Fei Li

Molecules 2010, 15(6), 4261-4266; https://doi.org/10.3390/molecules15064261 - 11 Jun 2010

Cited by 27 | Viewed by 14273

Abstract

This paper reports a novel synthesis of bosutinib starting from 3-methoxy-4-hydroxybenzoic acid. The process starts with esterification of the starting material, followed by alkylation, nitration, reduction, cyclization, chlorination and two successive amination reactions. The intermediates and target molecule were characterized by ¹H-NMR, [...] Read more.

This paper reports a novel synthesis of bosutinib starting from 3-methoxy-4-hydroxybenzoic acid. The process starts with esterification of the starting material, followed by alkylation, nitration, reduction, cyclization, chlorination and two successive amination reactions. The intermediates and target molecule were characterized by ¹H-NMR, ¹³C-NMR, MS and the purities of all the compounds were determined by HPLC. Full article

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Open AccessReview

Construction of Eight-Membered Carbocycles with Trisubstituted Double Bonds Using the Ring Closing Metathesis Reaction

by Motoo Tori and Reiko Mizutani

Molecules 2010, 15(6), 4242-4260; https://doi.org/10.3390/molecules15064242 - 11 Jun 2010

Cited by 50 | Viewed by 10616

Abstract

Medium sized carbocycles are particularly difficult to synthesize. Ring closing metathesis reactions (RCM) have recently been applied to construct eight-membered carbocycles, but trisubstituted double bonds in the eight-membered rings are more difficult to produce using RCM reactions. In this review, model examples and [...] Read more.

Medium sized carbocycles are particularly difficult to synthesize. Ring closing metathesis reactions (RCM) have recently been applied to construct eight-membered carbocycles, but trisubstituted double bonds in the eight-membered rings are more difficult to produce using RCM reactions. In this review, model examples and our own results are cited and the importance of the preparation of suitably designed precursors is discussed. Examples of RCM reactions used in the total synthesis of natural products are also outlined. Full article

(This article belongs to the Special Issue Ring-Closing Metathesis)

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Open AccessArticle

Evaluation of Carbohydrates in Natural and Cultured Cordyceps by Pressurized Liquid Extraction and Gas Chromatography Coupled with Mass Spectrometry

by Jia Guan, Feng-Qing Yang and Shao-Ping Li

Molecules 2010, 15(6), 4227-4241; https://doi.org/10.3390/molecules15064227 - 11 Jun 2010

Cited by 61 | Viewed by 12620

Abstract

Free and polymeric carbohydrates in Cordyceps, a valued edible mushroom and well-known traditional Chinese medicine, were determined using stepwise pressurized liquid extraction (PLE) extraction and GC-MS. Based on the optimized PLE conditions, acid hydrolysis and derivatization, ten monosaccharides, namely rhamnose, ribose, arabinose, [...] Read more.

Free and polymeric carbohydrates in Cordyceps, a valued edible mushroom and well-known traditional Chinese medicine, were determined using stepwise pressurized liquid extraction (PLE) extraction and GC-MS. Based on the optimized PLE conditions, acid hydrolysis and derivatization, ten monosaccharides, namely rhamnose, ribose, arabinose, xylose, mannose, glucose, galactose, mannitol, fructose and sorbose in 13 samples of natural and cultured Cordyceps were qualitatively and quantitatively analyzed and compared with myo-inositol hexaacetate as internal standard. The results showed that natural C. sinensis contained more than 7.99% free mannitol and a small amount of glucose, while its polysaccharides were usually composed of mannose, glucose and galactose with a molar ratio of 1.00:16.61~3.82:1.60~1.28. However, mannitol in cultured C. sinensis and cultured C. militaris were less than 5.83%, and free glucose was only detected in a few samples, while their polysaccharides were mainly composed of mannose, glucose and galactose with molar ratios of 1.00:3.01~1.09:3.30~1.05 and 1.00:2.86~1.28:1.07~0.78, respectively. Natural and cultured Cordyceps could be discriminated by hierarchical clustering analysis based on its free carbohydrate contents. Full article

(This article belongs to the Special Issue Phytochemicals with Signaling, Medicinal and Therapeutic Properties)

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308 KiB

Open AccessArticle

Free Radical Scavenging Activity and Anthocyanin Profile of Cabernet Sauvignon Wines from the Balkan Region

by Blaga Radovanović and Aleksandra Radovanović

Molecules 2010, 15(6), 4213-4226; https://doi.org/10.3390/molecules15064213 - 10 Jun 2010

Cited by 40 | Viewed by 9870

Abstract

The present study is focused on anthocyanin derivatives characterizing the antioxidant activity of Cabernet Sauvignon wines produced from different vineyard regions in the Balkans. These bioactive compounds were quantified with a high performance liquid chromatography (HPLC)-diode array detection (DAD) method. The antiradical activity [...] Read more.

The present study is focused on anthocyanin derivatives characterizing the antioxidant activity of Cabernet Sauvignon wines produced from different vineyard regions in the Balkans. These bioactive compounds were quantified with a high performance liquid chromatography (HPLC)-diode array detection (DAD) method. The antiradical activity was estimated by the ability of the wine to scavenge the stable 2,2`-diphenyl-1-picrylhydrazyl free radical (DPPH^·). The results show that the total anthocyanin content varied from 205.88 to 1940.28 mg/L, depending on agroclimatic factors and the enological practices of the corresponding vineyard region. The most prominent antocyanin in all investigated Cabernet Sauvignon wines was malvidin-3-O-monoglucoside, which accounted for 50.57% of total content, followed by its acetyl derivatives, 15.45%, and p-coumaryl derivatives 5.66%. The relationship between the anthocyanin derivatives and free radical scavenging activity is discussed. A high correlation between total anthocyanin content and DPPH· scavenging ability of tested wines was confirmed (r²= 0.9619). The significant correlations were obtained between antiradical activity and the sum of 3-monoglucoside (r²= 0.95594), the sum of 3-acetyl-3-glucoside (r²= 0.9728) and the sum of p-coumaryl-3-glucoside (r²= 0.8873) of wine samples. It can be concluded that, the anthocyanin composition can be used as biochemical marker for the authenticity of red grape cultivar and their corresponding single-cultivar wine. Full article

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383 KiB

Open AccessCommunication

An Effective Microwave-Induced Iodine-Catalyzed Method for the Synthesis of Quinoxalines via Condensation of 1,2-Diamines with 1,2-Dicarbonyl Compounds

by Debasish Bandyopadhyay, Sanghamitra Mukherjee, Robert R. Rodriguez and Bimal K. Banik

Molecules 2010, 15(6), 4207-4212; https://doi.org/10.3390/molecules15064207 - 9 Jun 2010

Cited by 69 | Viewed by 9376

Abstract

A microwave-induced iodine-catalyzed simple, rapid and convenient synthesis of different types of quinoxalines via condensation of 1,2-diamines with 1,2-dicarbonyl compounds has been accomplished with an excellent yield. Full article

(This article belongs to the Special Issue Organic Iodine Chemistry)

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126 KiB

Open AccessArticle

Synthesis of 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine via a [4+2] Cycloaddition

by Usama Karama, Adel Al-Saidey, Zeid Al-Othman and Abdel Rahman Almansour

Molecules 2010, 15(6), 4201-4206; https://doi.org/10.3390/molecules15064201 - 9 Jun 2010

Cited by 6 | Viewed by 7329

Abstract

The synthesis of the tetracyclic molecule 2-(9,10-dihydro-9,10-propano-anthracen-9-yl)-N-methylethanamine(2)as a homologue of the antidepressant 1-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethaneamine (1) was described. The key intermediate 9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one (7)was successfully synthesized via a [4+2] cycloaddition of α-bromoacrolein and 9-allyl-anthracene, followed by ring expansion and samarium diiodide deoxygenation. Full article

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286 KiB

Open AccessArticle

Rhodium-Catalyzed Linear Codimerization and Cycloaddition of Ketenes with Alkynes

by Teruyuki Kondo, Masatsugu Niimi, Yuki Yoshida, Kenji Wada, Take-aki Mitsudo, Yu Kimura and Akio Toshimitsu

Molecules 2010, 15(6), 4189-4200; https://doi.org/10.3390/molecules15064189 - 9 Jun 2010

Cited by 10 | Viewed by 7720

Abstract

A novel rhodium-catalyzed linear codimerization of alkyl phenyl ketenes with internal alkynes to dienones and a novel synthesis of furans by an unusual cycloaddition of diaryl ketenes with internal alkynes have been developed. These reactions proceed smoothly with the same rhodium catalyst, RhCl(PPh [...] Read more.

A novel rhodium-catalyzed linear codimerization of alkyl phenyl ketenes with internal alkynes to dienones and a novel synthesis of furans by an unusual cycloaddition of diaryl ketenes with internal alkynes have been developed. These reactions proceed smoothly with the same rhodium catalyst, RhCl(PPh₃)₃, and are highly dependent on the structure and reactivity of the starting ketenes. Full article

(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)

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510 KiB

Open AccessReview

Conazoles

by Jan Heeres, Lieven Meerpoel and Paul Lewi

Molecules 2010, 15(6), 4129-4188; https://doi.org/10.3390/molecules15064129 - 9 Jun 2010

Cited by 119 | Viewed by 15748

Abstract

This review provides a historical overview of the analog based drug discovery of miconazole and its congeners, and is focused on marketed azole antifungals bearing the generic suffix “conazole”. The antifungal activity of miconazole, one of the first broad-spectrum antimycotic agents has been [...] Read more.

This review provides a historical overview of the analog based drug discovery of miconazole and its congeners, and is focused on marketed azole antifungals bearing the generic suffix “conazole”. The antifungal activity of miconazole, one of the first broad-spectrum antimycotic agents has been mainly restricted to topical applications. The attractive in vitro antifungal spectrum was a starting point to design more potent and especially orally active antifungal agents such as ketoconazole, itraconazole, posaconazole, fluconazole and voriconazole. The chemistry, in vitro and in vivo antifungal activity, pharmacology, and clinical applications of these marketed conazoles has been described. Full article

(This article belongs to the Special Issue Anti-Infective Agents)

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244 KiB

Open AccessReview

Processing of Polymer Nanocomposites Reinforced with Polysaccharide Nanocrystals

by Alain Dufresne

Molecules 2010, 15(6), 4111-4128; https://doi.org/10.3390/molecules15064111 - 8 Jun 2010

Cited by 253 | Viewed by 17474

Abstract

Aqueous suspensions of polysaccharide (cellulose, chitin or starch) nanocrystals can be prepared by acid hydrolysis of biomass. The main problem with their practical use is related to the homogeneous dispersion of these nanoparticles within a polymeric matrix. Water is the preferred processing medium. [...] Read more.

Aqueous suspensions of polysaccharide (cellulose, chitin or starch) nanocrystals can be prepared by acid hydrolysis of biomass. The main problem with their practical use is related to the homogeneous dispersion of these nanoparticles within a polymeric matrix. Water is the preferred processing medium. A new and interesting way for the processing of polysaccharide nanocrystals-based nanocomposites is their transformation into a co-continuous material through long chain surface chemical modification. It involves the surface chemical modification of the nanoparticles based on the use of grafting agents bearing a reactive end group and a long compatibilizing tail. Full article

(This article belongs to the Special Issue Macromolecules: Chemistry, Medicinal and Functional Materials)

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104 KiB

Open AccessArticle

Synthesis of a New Series of N,N’-Dimethyltetrahydrosalen (H₂ [H₂Me]salen) Ligands by the Reductive Ring-Opening of 3,3'-Ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazines)

by Augusto Rivera, Jicli José Rojas, Jairo Salazar-Barrios, Mauricio Maldonado and Jaime Ríos-Motta

Molecules 2010, 15(6), 4102-4110; https://doi.org/10.3390/molecules15064102 - 7 Jun 2010

Cited by 4 | Viewed by 8353

Abstract

A new series of N,N'-bis(2'-hydroxy-5'-substituted-benzyl)-N,N´-dimethylethane-1,2-diamines (N,N'-dimethyltetrahydrosalen) ligands were prepared in good yield by reduction of the respective 3,3'-ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazine) precursors with sodium borohydride . The ligands were characterized by IR, NMR, and elemental [...] Read more.

A new series of N,N'-bis(2'-hydroxy-5'-substituted-benzyl)-N,N´-dimethylethane-1,2-diamines (N,N'-dimethyltetrahydrosalen) ligands were prepared in good yield by reduction of the respective 3,3'-ethylene-bis(3,4-dihydro-6-substituted-2H-1,3-benzoxazine) precursors with sodium borohydride . The ligands were characterized by IR, NMR, and elemental analysis, which showed the compounds to be consistent with the proposed structures. Ring-opening reactions of bis-1,3-benzoxazines in the presence of sodium borohydride to produce N,N’-dimethylated tetrahydrosalens (H₂ [H₂Me]salen) have not been reported in the literature. Full article

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115 KiB

Open AccessArticle

An Expeditious Synthesis of [1,2]Isoxazolidin-5-ones and [1,2]Oxazin-6-ones from Functional Allyl Bromide Derivatives

by Imen Beltaïef, Aïcha Arfaoui and Hassen Amri

Molecules 2010, 15(6), 4094-4101; https://doi.org/10.3390/molecules15064094 - 7 Jun 2010

Cited by 3 | Viewed by 8293 | Retraction

Abstract

Reaction of allyl bromide (Z)-1 and (Z)-2 with N-substituted hydroxylamine hydrochlorides in presence of tert-butoxide in tert-butanol at reflux provides a short and effective route to [1,2]isoxazolidin-5-ones 3 and [1,2]oxazin-6-ones 4. Full article

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165 KiB

Open AccessArticle

Synthesis and Biological Evaluation of a γ-Cyclodextrin-based Formulation of the Anticancer Agent 5,6,11,12,17,18,23,24- Octahydrocyclododeca[1,2-b:4,5-b’:7,8-b’’:10,11-b’’’]tetraindole (CTet)

by Simone Lucarini, Mauro De Santi, Francesca Antonietti, Giorgio Brandi, Giuseppe Diamantini, Alessandra Fraternale, Maria Filomena Paoletti, Andrea Tontini, Mauro Magnani and Andrea Duranti

Molecules 2010, 15(6), 4085-4093; https://doi.org/10.3390/molecules15064085 - 4 Jun 2010

Cited by 12 | Viewed by 11417

Abstract

5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b’:7,8-b’’:10,11- b’’’]tetrai ndole (CTet), an indole-3-carbinol (I3C) metabolite endowed with anticancer properties, is poorly soluble in the solvents most frequently used in biological tests. This study indicates that the use of γ-cyclodextrin (γ-CD) avoids this problem. Formulated with γ-CD CTet is a potent [...] Read more.

5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b’:7,8-b’’:10,11- b’’’]tetrai ndole (CTet), an indole-3-carbinol (I3C) metabolite endowed with anticancer properties, is poorly soluble in the solvents most frequently used in biological tests. This study indicates that the use of γ-cyclodextrin (γ-CD) avoids this problem. Formulated with γ-CD CTet is a potent inhibitor of DNA synthesis in both estrogen receptor positive (MCF-7) and estrogen receptor negative (MDA-MB-231) human breast cell lines (IC50 = 1.20 ± 0.04 μM and 1.0 ± 0.1 μM, respectively). Full article

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2312 KiB

Open AccessArticle

Pharmaceutical Composition of Valsartan: β-Cyclodextrin: Physico–Chemical Characterization and Anti-Hypertensive Evaluation

by Carlos Eduardo De Matos Jensen, Robson Augusto Souza Dos Santos, Angelo Márcio Leite Denadai, Cynthia Fernandes Ferreira Santos, Aline Nardoni Gonçalves Braga and Rubén Dario Sinisterra

Molecules 2010, 15(6), 4067-4084; https://doi.org/10.3390/molecules15064067 - 4 Jun 2010

Cited by 50 | Viewed by 14412

Abstract

Valsartan, a water-insoluble drug, is mainly used in the treatment of hypertension albeit with reduced oral bioavailability. The aim of work was to develop a valsartan:β-cyclodextrin (VAL:β-CD) pharmaceutical composition in order to improve its water solubility and bioavailability. The VAL:β-CD complexes were prepared [...] Read more.

Valsartan, a water-insoluble drug, is mainly used in the treatment of hypertension albeit with reduced oral bioavailability. The aim of work was to develop a valsartan:β-cyclodextrin (VAL:β-CD) pharmaceutical composition in order to improve its water solubility and bioavailability. The VAL:β-CD complexes were prepared by the kneading, solid dispersion and freeze-drying methods, of which the freeze-drying method (FDY) was found to be the best to prepare an inclusion complex. A physical mixtyure PM was also prepared. Complexes were characterized by thermal analysis, Fourier transformed- infrared (FTIR) spectroscopy, Powder X-ray diffractometry, intrinsic dissolution and NMR (2D-ROESY). Phase-solubility analysis showed A_L-type diagrams with β-cyclodextrin (β-CD). Microcalorimetric titrations suggested the formation of 1:1 inclusion complex between VAL and β-CD. The apparent stability constants K_1:1 calculated from phase-solubility plots were 165.4 M^-1(298 K), 145.0 M^-1(303 K) and 111.3 M^-1(310 K). In vivo experiments in rats showed that reduction in arterial pressure for the FDY complex is better than with valsartan used alone. The better activity of FDY can be attributed to the higher solubility of valsartan after inclusion in the cyclodextrin cavity, as suggest by the intrinsic dissolution studies. Full article

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Molecules, Volume 15, Issue 6 (June 2010) – 48 articles , Pages 3775-4489

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