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Selected Papers from the “2nd International Conference on Natural Products and Physiologically Active Substances” (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry”

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (17 September 2004) | Viewed by 131318

Special Issue Editors

Terpenoids Laboratory, Novosibirsk Institute of Organic Chemistry, 9 Acad. Lavrentjev Ave., 630090 Novosibirsk, Russia
Interests: study of chemical communication of taiga tick Ixodes persulcatus and siberian moth Dendrolimus superans; chemistry of nitrogen-containing terpenoids; study of oxidative transformation of lower terpenoids; development of new methods of utilization of the terpenoids-containing plant raw materials; syntheses based on available natural terpenoids; synthesis and study of chiral terpenoids-based transition metal ions; study of chemical structure and conformational behavior of natural terpenoids and synthetic derivatives; NMR spectroscopy of natural products; computational methods in organic chemistry and education
Department of Civil Engineering, University of Porto, 4200-465 Porto, Portugal
Interests: numerical modeling of engineering structures and structural components (offshore applications, steel bridges, pressure vessels, pipelines, wind turbine towers, etc.); mathematical problems in fatigue and fracture; mechanics of solids and structures; metals materials and structures; numerical fracture mechanics and crack growth; local approaches; finite element methods in structural mechanics applications; computer-aided structural integrity
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Published Papers (13 papers)

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Editorial

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101 KiB  
Editorial
Special Issue: Selected Papers from the 2nd International Conference on Natural Products and Physiologically Active Substances (ICNPAS-2004) and the 3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry” (EAHM-2004)
by Eugene V. Babaev and Alexey V. Tkachev
Molecules 2005, 10(9), 1021-1022; https://doi.org/10.3390/10091021 - 30 Sep 2005
Cited by 1 | Viewed by 5396
Abstract
Two meetings, ICNPAS-2004 and EAHM-2004, were jointly held on September 12-17, 2004 in Novosibirsk, Russia.[...] Full article

Research

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137 KiB  
Article
Synthesis of Oxadiazoles, Thiadiazoles and Triazoles Derived from Benzo[b]thiophene
by A. Sharba, R. Al-Bayati, M. Aouad and N. Rezki
Molecules 2005, 10(9), 1161-1168; https://doi.org/10.3390/10091161 - 30 Sep 2005
Cited by 26 | Viewed by 12576
Abstract
In this work 3-chloro-2-chlorocarbonylbenzo[b]thiophene (1) was prepared from cinnamic acid and then converted into the acid hydrazide 2. The azomethines 3a-e were prepared from the corresponding aryl aldehydes and the acid hydrazide 2. Treatment of compound 2 with formic acid gave the N-formyl [...] Read more.
In this work 3-chloro-2-chlorocarbonylbenzo[b]thiophene (1) was prepared from cinnamic acid and then converted into the acid hydrazide 2. The azomethines 3a-e were prepared from the corresponding aryl aldehydes and the acid hydrazide 2. Treatment of compound 2 with formic acid gave the N-formyl acid hydrazide 4, which upon refluxing with phosphorous pentoxide or phosphorous pentasulphide in xylene yielded the corresponding 2- (3-chloro-1-benzothien-2-yl)-1,3,4-oxadiazole (5) and 2-(3-chloro-1-benzo-thien-2-yl)-1,3,4- thiadiazole (6). Reaction of 1-thiosemicarbazide 7 with NaOH leads to ring closure giving 5- (3-chloro-1-benzothien-2- yl)-4H–triazole-3-thiol (8) which is converted into a number of derivatives 9-12 Reaction of 2 with phenyl isothiocyanate and NaOH afforded 5-(3-chloro- 1-benzothien-2-yl)-4-(phenyl)-4H-1,2,4-triazole-3-thiol (14). Full article
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198 KiB  
Article
Synthesis of Thiadiazoles and 1,2,4-Triazoles Derived from Cyclopropane Dicarboxylic Acid
by A. Sharba, R. Al-Bayati, N. Rezki and M. Aouad
Molecules 2005, 10(9), 1153-1160; https://doi.org/10.3390/10091153 - 30 Sep 2005
Cited by 20 | Viewed by 10133
Abstract
New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1) with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- yl)cyclopropane (2). Cyclopropane dicarboxylic acid thiosemicarbazide (6) was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl) cyclo- propane (7) [...] Read more.
New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1) with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- yl)cyclopropane (2). Cyclopropane dicarboxylic acid thiosemicarbazide (6) was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl) cyclo- propane (7) by ring closure in an alkaline medium. The thiadiazole 2 and the triazole 7 were converted into a variety of derivatives. Full article
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75 KiB  
Article
Oxidative Stress, Lipid Profile and Liver Functions in Average Egyptian Long Term Depo Medroxy Progesterone Acetate (DMPA) Users
by L. Faddah, M. Al-Rehany, N. Abdel-Hamid and A. Bakeet
Molecules 2005, 10(9), 1145-1152; https://doi.org/10.3390/10091145 - 30 Sep 2005
Cited by 22 | Viewed by 14731
Abstract
Depo-medroxy progesterone acetate (DMPA, Depo-Provera®) is used in morethan 80 countries as a long-acting contraceptive administered as a single intramuscular(i.m) injection of 150 mg/3 months. The present study was set up to investigate theeffects of DMPA on 80 average Egyptian women [...] Read more.
Depo-medroxy progesterone acetate (DMPA, Depo-Provera®) is used in morethan 80 countries as a long-acting contraceptive administered as a single intramuscular(i.m) injection of 150 mg/3 months. The present study was set up to investigate theeffects of DMPA on 80 average Egyptian women classified into four groups comprisingthose using the drug for one, two, three and four years, respectively, compared to acontrol group (N = 20) of married non-hormonally – treated women of similar ages. Thedrug showed a transient significant elevation of alanine aminotransferase activity (ALT)without an apparent effect on other liver indices, namely total bilirubin (T.Bil) level,aspartate aminotransferase (AST) and alkaline phosphatase (ALP) activities. Only thelow density/high density lipoproteins cholesterol ratio (LDLC/HDLC) was gradually andnon-significantly (ns) increased in comparison to control group, however, neither totalcholesterol (TC) nor triglycerides (TG) were affected by the drug. The lipid peroxideproduct malondialdehyde (MDA) was significantly elevated in an gradual manner with acorresponding decrease in reduced glutathione (GSH), without any change in blood nitricoxide (NO) levels. It can be concluded that DMPA may be considered as a safecontraceptive medication for the studied group of women, but that special care should beexercised for cardiovascular, hepatic and other patients more sensitive to the harmfuleffects of free radicals. Alternatively, supportive medications are advisable for eachexposed case to secure against the possible irreversible adverse effects of the drug by continuous use. In addition, annual re-evaluation is much more advisable despite the proven safety of the drug. Full article
256 KiB  
Article
Poly[3-(3,4-dihydroxyphenyl)glyceric Acid], A New Biologically Active Polymer from Symphytum Asperum Lepech. and S.Caucasicum Bieb. (Boraginaceae)
by V. Barbakadze, E. Kemertelidze, I. Targamadze, K. Mulkijanyan, A. Shashkov and A. Usov
Molecules 2005, 10(9), 1135-1144; https://doi.org/10.3390/10091135 - 30 Sep 2005
Cited by 24 | Viewed by 9273
Abstract
Two high-molecular water-soluble preparations with high anticomplementary, antioxidant, antilipoperoxidant and antiinflammatory activities were isolated from the roots of Symphytum asperum and S. caucasicum. Their main chemical constituent was found to be poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], according to IR and NMR spectroscopy. The Symphytum high-molecular preparations can [...] Read more.
Two high-molecular water-soluble preparations with high anticomplementary, antioxidant, antilipoperoxidant and antiinflammatory activities were isolated from the roots of Symphytum asperum and S. caucasicum. Their main chemical constituent was found to be poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], according to IR and NMR spectroscopy. The Symphytum high-molecular preparations can modulate in vitro B- chronic lymphocytic leukaemia (B-CLL) cells apoptosis and cell cycle progression. Full article
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160 KiB  
Article
New Multi-1,2,3-Selenadiazole Aromatic Derivatives
by M. Al-Smadi and S. Ratrout
Molecules 2005, 10(9), 1126-1134; https://doi.org/10.3390/10091126 - 30 Sep 2005
Cited by 12 | Viewed by 8807 | Retraction
Abstract
The aromatic polyketones 3a-d are versatile compounds for the synthesis of the multi-1,2,3-selenadiazole aromatic derivatives 1a-d. The preparation starts with the reaction between the multi-bromomethylene benzene derivatives 2a-d and 4-hydroxy- acetophenone to give compounds 3a-d which are transformed through the reaction with semicarbazide [...] Read more.
The aromatic polyketones 3a-d are versatile compounds for the synthesis of the multi-1,2,3-selenadiazole aromatic derivatives 1a-d. The preparation starts with the reaction between the multi-bromomethylene benzene derivatives 2a-d and 4-hydroxy- acetophenone to give compounds 3a-d which are transformed through the reaction with semicarbazide hydrochloride or ethyl hydrazine carboxylate into the corresponding semicarbazones derivatives 4a-d or hydrazones 5a-d. The reaction with selenium dioxide leads to regiospecific ring closure of semicarbazones or hydrazones to give the multi- 1,2,3-selenadiazole aromatic derivatives in high yield. Full article
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132 KiB  
Article
A Facile Synthesis of Novel Herbicidal 1-Phenyl-piperazine-2,6-diones
by B. Li, D. Xiang, C. Hsu, Z. Liu, C. Wu and H. Yang
Molecules 2005, 10(9), 1119-1125; https://doi.org/10.3390/10091119 - 30 Sep 2005
Cited by 1 | Viewed by 8251
Abstract
Novel 1-phenyl-piperazine-2,6-diones were prepared by a new facile synthetic routeusing methyl N-substituted iminomonoacetate as starting material. The structures of thesecompounds were established by 1H-NMR, 13C-NMR and GC/MS. 2-(4-Chloro-5-cyclo-pentyl-oxy-2-fluorophenyl)-tetrahydro-2H-pyrido-[1,2-a]-pyrazine-1,3-(4H,6H)-dione displayed thegreatest herbicidal activity. Full article
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225 KiB  
Article
The tert-Amino Effect in Heterocyclic Chemistry. Synthesis of Spiro Heterocycles
by E. D’yachenko, T. Glukhareva, L. Dyudya, O. Eltsov and Y. Morzherin
Molecules 2005, 10(9), 1101-1108; https://doi.org/10.3390/10091101 - 30 Sep 2005
Cited by 18 | Viewed by 9973
Abstract
The tert-amino reaction effect was examined. A new method to synthesize spiro heterocycles is presented. It was shown that the “tert-amino effect” could be applied to the formation of spiro-fused heterocycles. The formation of spiro compounds proceeds in most cases in good yields [...] Read more.
The tert-amino reaction effect was examined. A new method to synthesize spiro heterocycles is presented. It was shown that the “tert-amino effect” could be applied to the formation of spiro-fused heterocycles. The formation of spiro compounds proceeds in most cases in good yields in a one-pot reaction. Full article
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265 KiB  
Article
Studies Towards the Total Synthesis of Di- and Sesterterpenes with Dicyclopenta[a,d]cyclooctane Skeletons. Three-component Approach to the A/B Rings Building Block
by K. Michalak, M. Michalak and J. Wicha
Molecules 2005, 10(9), 1084-1100; https://doi.org/10.3390/10091084 - 30 Sep 2005
Cited by 22 | Viewed by 10184
Abstract
Sesqui- and sesterterpenes of ophiobolin and fusicoccin families are important synthetic targets because of complexity of structure and potentially useful physiological activities, including anti-tumor activity. A synthesis of versatile building blocks for these terpenoids is described. Cyclopenta[8]annulene rings system with properly dislocated substituents [...] Read more.
Sesqui- and sesterterpenes of ophiobolin and fusicoccin families are important synthetic targets because of complexity of structure and potentially useful physiological activities, including anti-tumor activity. A synthesis of versatile building blocks for these terpenoids is described. Cyclopenta[8]annulene rings system with properly dislocated substituents was constructed using as key steps ring closing metathesis reaction and Wagner - Meerwein rearrangement. Ring closing metathesis reaction leading to cyclopenta[8]annulene was studied in detail. Full article
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175 KiB  
Article
An Improved Synthesis of Some 5-Substituted Indolizines Using Regiospecific Lithiation
by Alexey G. Kuznetsov, Alexander A. Bush, Viktor B. Rybakov and Eugene V. Babaev
Molecules 2005, 10(9), 1074-1083; https://doi.org/10.3390/10091074 - 30 Sep 2005
Cited by 23 | Viewed by 9353
Abstract
Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyl- and 5-iodoindolizine have been prepared by this way and the molecular structure [...] Read more.
Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyl- and 5-iodoindolizine have been prepared by this way and the molecular structure of 5-formyl-2- phenylindolizine was confirmed by X-Ray analysis. The reactivity of the 5-CHO- and 5- COPh groups toward some nucleophiles has been examined, and some additional classes of derivatives (oximes and alcohols) have been obtained. The possibility of Suzuki cross- coupling of 5-iodoindolizines and boronic acids was proven. Full article
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440 KiB  
Article
The Preparation of New Phosphorus-Centered Functional Groups for Modified Oligonucleotides and Other Natural Phosphates
by A. Gautier, C. Lopin, G. Garipova, O. Dubert, I. Kalinina, C. Salcedo, S. Balieu, S. Glatigny, J. Valnot, G. Gouhier and S. Piettre
Molecules 2005, 10(9), 1048-1073; https://doi.org/10.3390/10091048 - 30 Sep 2005
Cited by 5 | Viewed by 9938
Abstract
Efforts to develop synthetic methodologies allowing the preparation of α,α– difluorophosphonothioates, α,α–difluorophosphonodithioates, α,α–difluorophosphono- trithioates, and α,α–difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphates. Two successful approaches have been developed, based either on the addition [...] Read more.
Efforts to develop synthetic methodologies allowing the preparation of α,α– difluorophosphonothioates, α,α–difluorophosphonodithioates, α,α–difluorophosphono- trithioates, and α,α–difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphates. Two successful approaches have been developed, based either on the addition of phosphorus-centered radicals onto gem–difluoroalkenes or on a process involving the addition of lithiodifluorophosphono- thioates 91 onto a ketone and the subsequent deoxygenation reaction of the adduct. The radical route successfully developed a practical route to α,α–difluoro–H–phosphinates which proved to be useful intermediates to a variety of phosphate isosters. The ionic route led to the first preparation of phosphonodifluoromethyl analogues of nucleoside– 3’–phosphates. Full article
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251 KiB  
Article
Dakin-West Trick in the Design of Novel 2-Alkyl(aralkyl) Derivatives of Oxazolo[3,2-a]pyridines
by Zeinul-Gabiden M. Kazhkenov, Alexander A. Bush and Eugene V. Babaev
Molecules 2005, 10(9), 1109-1118; https://doi.org/10.3390/10091109 - 01 Sep 2005
Cited by 9 | Viewed by 8305
Abstract
A series of previously unavailable derivatives of 2-alkyl- and 2-benzylderivatives of oxazolo[3,2-a]pyridines III were obtained via tandem ring opening and ring closure from stable mesoionic 3-acyloxazolo[3,2-a]pyridinium-2-olates I. The key intermediates of this tandem transformation are N-(b-oxoethyl)pyridones-2 II obtained by Dakin-West acylation of (pyridone-2-yl-1)acetic [...] Read more.
A series of previously unavailable derivatives of 2-alkyl- and 2-benzylderivatives of oxazolo[3,2-a]pyridines III were obtained via tandem ring opening and ring closure from stable mesoionic 3-acyloxazolo[3,2-a]pyridinium-2-olates I. The key intermediates of this tandem transformation are N-(b-oxoethyl)pyridones-2 II obtained by Dakin-West acylation of (pyridone-2-yl-1)acetic acid. An example of further utilization of this strategy is illustrated by preparation of unknown 2-benzylimidazo[1,2-a]pyridine from the salt I and ammonia. Full article
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Other

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460 KiB  
Other
Organic Synthesis in Pheromone Science
by Kenji Mori
Molecules 2005, 10(9), 1023-1047; https://doi.org/10.3390/10091023 - 30 Sep 2005
Cited by 5 | Viewed by 13507
Abstract
Examples are given to illustrate the use of chemical and/or enzymatic asymmetric reactions in the synthesis of the new pheromones of the broad-horned flour beetle, flea beetle, currant stem girdler and Colorado potato beetle. The relationships between stereochemistry and bioactivity among pheromones are [...] Read more.
Examples are given to illustrate the use of chemical and/or enzymatic asymmetric reactions in the synthesis of the new pheromones of the broad-horned flour beetle, flea beetle, currant stem girdler and Colorado potato beetle. The relationships between stereochemistry and bioactivity among pheromones are summarized to emphasize biodiversity as revealed in pheromone perception. Full article
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