Molbank

5 pages, 910 KiB

Open AccessShort Note

Synthesis and Crystal Structure of A Pyrithione Derivative: Bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium} tetrachlorocuprate(2-)

by Łukasz Balewski, Franciszek Sączewski and Maria Gdaniec

Molbank 2019, 2019(2), M1067; https://doi.org/10.3390/M1067 - 25 Jun 2019

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Abstract

The pyrithione derivative, bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium} tetrachlorocuprate(2-) (1a) has been obtained by the reaction of one equivalent of 2-[(4,5-dihydro-1H-imidazol-2-yl)thio]pyridine 1-oxide hydrochloride with one and a half equivalents of copper (II) chloride dihydrate in methanol in a very good yield. [...] Read more.

The pyrithione derivative, bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium} tetrachlorocuprate(2-) (1a) has been obtained by the reaction of one equivalent of 2-[(4,5-dihydro-1H-imidazol-2-yl)thio]pyridine 1-oxide hydrochloride with one and a half equivalents of copper (II) chloride dihydrate in methanol in a very good yield. The structure of this product was confirmed by X-ray crystallography, infrared spectroscopy, and elemental analysis. Full article

(This article belongs to the Section Structure Determination)

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11 pages, 2680 KiB

Open AccessShort Note

α-d-Glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d-fructofuranoside]

by Kwaku Kyeremeh, Samuel Kwain, Gilbert Mawuli Tetevi, Anil Sazak Camas, Mustafa Camas, Aboagye Kwarteng Dofuor, Hai Deng and Marcel Jaspars

Molbank 2019, 2019(2), M1066; https://doi.org/10.3390/M1066 - 16 Jun 2019

Cited by 2 | Viewed by 3696

Abstract

The Mycobacterium sp. BRS2A-AR2 is an endophyte of the mangrove plant Rhizophora racemosa G. Mey., which grows along the banks of the River Butre, in the Western Region of Ghana. Chemical profiling using ¹H-NMR and HRESI-LC-MS of fermentation extracts produced by the [...] Read more.

The Mycobacterium sp. BRS2A-AR2 is an endophyte of the mangrove plant Rhizophora racemosa G. Mey., which grows along the banks of the River Butre, in the Western Region of Ghana. Chemical profiling using ¹H-NMR and HRESI-LC-MS of fermentation extracts produced by the strain led to the isolation of the new compound, α-d-Glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d–fructofuranoside] or simply tortomycoglycoside (1). Compound 1 is an aminoglycoside consisting of a tryptophan moiety esterified to a disaccharide made up of β-d-fructofuranose and α-d-glucopyranose sugars. The full structure of 1 was determined using UV, IR, 1D, 2D-NMR and HRESI-LC-MS data. When tested against Trypanosoma brucei subsp. brucei, the parasite responsible for Human African Trypanosomiasis in sub-Saharan Africa, 1 (IC₅₀ 11.25 µM) was just as effective as Coptis japonica (Thunb.) Makino. (IC₅₀ 8.20 µM). The extract of Coptis japonica (Thunb.) Makino. is routinely used as laboratory standard due to its powerful antitrypanosomal activity. It is possible that, compound 1 interferes with the normal uptake and metabolism of tryptophan in the T. brucei subsp. brucei parasite. Full article

(This article belongs to the Section Natural Products)

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5 pages, 494 KiB

Open AccessCommunication

N-Propargylation of Indolo-Triterpenoids and Their Application in Mannich Reaction

by Elmira F. Khusnutdinova, Anastasiya V. Petrova, Gulnaz M. Bashirova and Oxana B. Kazakova

Molbank 2019, 2019(2), M1065; https://doi.org/10.3390/M1065 - 13 Jun 2019

Cited by 3 | Viewed by 1762

Abstract

The introduction of the alkynyl moiety to the triterpenic core through a linkage to the indole nitrogen is described. The reaction of N-propargylindoles with N-methylpiperazine using Mannich reaction led to propargylaminoalkynyl-triterpenoids, whose structures were established by NMR spectroscopy. Full article

(This article belongs to the Section Natural Products)

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4 pages, 712 KiB

Open AccessShort Note

5,5′-Thiobis(3-methoxy-4H-1,2,6-thiadiazin-4-one)

by Andreas S. Kalogirou and Panayiotis A. Koutentis

Molbank 2019, 2019(2), M1064; https://doi.org/10.3390/M1064 - 9 Jun 2019

Viewed by 1821

Abstract

The reaction of 3-chloro-5-methoxy-4H-1,2,6-thiadiazin-4-one (9) with Na₂S·9H₂O (0.5 equiv) in tetrahydrofuran (THF) at ca. 20 °C for 20 h gives 5,5′-thiobis(3-methoxy-4H-1,2,6-thiadiazin-4-one) (10) in a 44% yield as yellow needles. The compound was fully characterized. Full article

(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)

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8 pages, 478 KiB

Open AccessCommunication

(E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxy-phenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one and (E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one

by Hery Suwito, Noorma Kurnyawaty, Ellyca Susetyo, Yuzkiya Azizah, Kautsar Ul Haq, Alfinda Novi Kristanti and Indriani Indriani

Molbank 2019, 2019(2), M1063; https://doi.org/10.3390/M1063 - 4 Jun 2019

Viewed by 1990

Abstract

Dihydropyrimidine derivatives possess great potential to be used as a precursor for the synthesis of wide diverse dihydropyrimidine-like derivatives. In this research, the title compounds were synthesized through the reaction between 5-acetyl-4-(2,5-dimethoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione and 2,5-dimethoxybenzladehyde under aldol condensation condition. The title compound, [...] Read more.

Dihydropyrimidine derivatives possess great potential to be used as a precursor for the synthesis of wide diverse dihydropyrimidine-like derivatives. In this research, the title compounds were synthesized through the reaction between 5-acetyl-4-(2,5-dimethoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione and 2,5-dimethoxybenzladehyde under aldol condensation condition. The title compound, (E)-3-(2,5-dimethoxyphenyl)-1-{[(4-(2,5-dimethoxyphenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)]}prop-2-en-1-one (yield 15%), was obtained as major product, whereas (E)-3-(2,5-dimethoxyphenyl)-1-{[(4-(2,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro pyrimidin-5-yl)]}prop-2-en-1-one (yield 8%) as side product through vinylogous aldol condensation. Full article

(This article belongs to the Special Issue Molecules from Multicomponent Reactions)

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6 pages, 746 KiB

Open AccessCommunication

(2S,5R)-2-Isopropyl-5-methylcyclohexanone Hydrazones

by Mariia Nesterkina, Dmytro Barbalat, Ivan Zheltvay, Ildar Rakipov, Mehmet Atakay, Bekir Salih and Iryna Kravchenko

Molbank 2019, 2019(2), M1062; https://doi.org/10.3390/M1062 - 29 May 2019

Cited by 6 | Viewed by 2701

Abstract

Hydrazones were obtained in 76–78% yield via condensation of (2S,5R)-2-isopropyl-5-methylcyclohexanone with 4-R-phenoxyacetic acid hydrazides in the presence of a catalytic amount of glacial acetic acid. The structure of the target compounds has been established by FTIR-ATR, Raman, [...] Read more.

Hydrazones were obtained in 76–78% yield via condensation of (2S,5R)-2-isopropyl-5-methylcyclohexanone with 4-R-phenoxyacetic acid hydrazides in the presence of a catalytic amount of glacial acetic acid. The structure of the target compounds has been established by FTIR-ATR, Raman, ¹H-NMR and ¹³C-NMR spectral analysis and EI/FAB/ESI mass spectrometry. Thermal properties of hydrazones 3a–3e were elucidated by differential scanning calorimetry (DSC) and their purity by HPLC coupled to mass spectrometry. Synthesized compounds were found to exist as Z/E geometrical isomers about C=N bond and cis/trans amide conformers. Full article

(This article belongs to the Collection Molecules from Catalytic Processes)

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7 pages, 602 KiB

Open AccessCommunication

4b,5,6,9-Tetrahydro-7H-dibenzo[c,e]pyrrolo[1,2-a]azepin-7-one

by Maksim A. Boichenko, Igor Yu. Babkin, Sergey G. Kobylskoy, Alexey O. Chagarovskiy, Olga A. Ivanova and Igor V. Trushkov

Molbank 2019, 2019(2), M1061; https://doi.org/10.3390/M1061 - 17 May 2019

Cited by 1 | Viewed by 2316

Abstract

A simple approach to synthesize 4b,5,6,9-tetrahydro-7H-dibenzo[c,e]pyrrolo[1,2-a]azepin- 7-one has been developed, based on a three-step transformation of 2-(2-bromophenyl)cyclopropane-1,1-diester. The key stage in this method is an intramolecular cross-coupling of 1-(2-bromobenzyl)-5-(2-bromophenyl)pyrrolidin-2-one under continuous flow conditions in an H-Сube-Pro using commercially available supported Pd catalysts. Full article

(This article belongs to the Collection Molecules from Catalytic Processes)

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9 pages, 956 KiB

Open AccessCommunication

Synthesis of 1H-3-{4-[(3-Dimethylaminopropyl)aminomethyl]phenyl}-2-phenylindole and Evaluation of Its Antiprotozoal Activity

by Jean Guillon, Clotilde Boudot, Anita Cohen, Solène Savrimoutou, Sandra Rubio, Vittoria Milano, Mathieu Marchivie, Nadine Azas, Catherine Mullié, Pascal Sonnet and Bertrand Courtioux

Molbank 2019, 2019(2), M1060; https://doi.org/10.3390/M1060 - 9 May 2019

Cited by 4 | Viewed by 1996

Abstract

1H-3-{4-[(3-Dimethylaminopropyl)aminomethyl]phenyl}-2-phenylindole was synthesized via a multi-step pathway starting from 2-iodoaniline. Structure characterization of this new indole compound was achieved by ¹H-NMR, ¹³C-NMR and ESI-MS spectral analysis. The title compound was screened in vitro against three protozoan parasites (Plasmodium [...] Read more.

1H-3-{4-[(3-Dimethylaminopropyl)aminomethyl]phenyl}-2-phenylindole was synthesized via a multi-step pathway starting from 2-iodoaniline. Structure characterization of this new indole compound was achieved by ¹H-NMR, ¹³C-NMR and ESI-MS spectral analysis. The title compound was screened in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani and Trypanosoma brucei brucei). Biological results showed antiparasitic activity with IC₅₀ values in the μM range. Full article

(This article belongs to the Section Organic Synthesis)

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5 pages, 899 KiB

Open AccessShort Note

5-[(Z)-5-Chloro-2-oxoindolin-3-ylidene]-3-{(E)-[(4-hydroxyphenyl)imino]methyl}-2-thioxothiazolidin-4-one

by Abdelmounaim Safer, Khadidja Khaldoun and Salima Saidi-Besbes

Molbank 2019, 2019(2), M1059; https://doi.org/10.3390/M1059 - 6 May 2019

Viewed by 1625

Abstract

N-aminorhodanine as well as isatin are highly solicited motifs known for their wide potential for biological activity. The objective of this work was to synthesize hybrid molecules as kinase inhibitors from these two motifs. In order to study the reactivity of the [...] Read more.

N-aminorhodanine as well as isatin are highly solicited motifs known for their wide potential for biological activity. The objective of this work was to synthesize hybrid molecules as kinase inhibitors from these two motifs. In order to study the reactivity of the two active centers in aminorhodanine (N-amino group and the 5-methylene group) toward two carbonyl groups (aromatic aldehyde and ketone of isatin), we decided to carry out a one-pot multi-component reaction by simultaneously introducing aminorhodanine, isatin, and an aromatic aldehyde in ethanol in the presence of AcOEt. Under these conditions, this reaction led to a single adduct. The reaction product structure was confirmed by ¹H, ¹³C-NMR, X-ray single crystal analysis, and high-resolution mass HRMS analysis. As a result, the method used has been very effective and totally stereo- and regioselective. Full article

(This article belongs to the Special Issue Molecules from Multicomponent Reactions)

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5 pages, 378 KiB

Open AccessShort Note

(E)-N′-(4-Fluorobenzylidene)-5-methyl-2-(pyridin-3-yl)thiazole-4-carbohydrazide

by Vinuta Kamat, Rangappa Santosh and Suresh P. Nayak

Molbank 2019, 2019(2), M1058; https://doi.org/10.3390/M1058 - 2 May 2019

Viewed by 2096

Abstract

5-methyl-2-(pyridin-3-yl)-1,3-thiazole-4-carbohydrazide (1) on treatment with 4-fluorobenzaldehyde in presence of catalytic amount of acetic acid, accessed the target compound (2) with the yield of 79%. The target compound was confirmed by ¹H-NMR, ¹³C-NMR, FT-IR and LCMS. In vitro [...] Read more.

5-methyl-2-(pyridin-3-yl)-1,3-thiazole-4-carbohydrazide (1) on treatment with 4-fluorobenzaldehyde in presence of catalytic amount of acetic acid, accessed the target compound (2) with the yield of 79%. The target compound was confirmed by ¹H-NMR, ¹³C-NMR, FT-IR and LCMS. In vitro antibacterial activity against Staphylococcus aureus (S. Aureus), Bacillus subtilis (B. subtilis), Escherichia coli (E. coli), and Pseudomonas aeruginosa (P. aeruginosa) were carried out and compound 2 showed promising activity against B. subtilis. In addition, compound 2 was analyzed for DNA binding study. It revealed that compound 2 has a promising affinity towards DNA double helix. Full article

(This article belongs to the Collection Molecules from Catalytic Processes)

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Scheme 1

7 pages, 1417 KiB

Open AccessShort Note

A Ternary Nickel(II) Schiff Base Complex Containing Di-Anionic and Neutral Forms of a Dithiocarbazate Schiff Base

by Enis Nadia Md Yusof, Nazhirah Muhammad Nasri, Thahira B. S. A. Ravoof and Edward R.T. Tiekink

Molbank 2019, 2019(2), M1057; https://doi.org/10.3390/M1057 - 23 Apr 2019

Cited by 4 | Viewed by 1850

Abstract

The title Ni^II complex, Ni(L)(LH₂) (1), where LH₂ is S-2-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene) dithiocarbazate, was isolated from the reaction of Ni(acetate)₂·4H₂O and two molar equivalents of LH₂. The complex was characterized [...] Read more.

The title Ni^II complex, Ni(L)(LH₂) (1), where LH₂ is S-2-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene) dithiocarbazate, was isolated from the reaction of Ni(acetate)₂·4H₂O and two molar equivalents of LH₂. The complex was characterized by elemental analysis, spectroscopy (IR and UV) as well as by a single-crystal X-ray structure determination. The nickel(II) center is coordinated within a cis-NOS₂ donor set that defines a square planar geometry. Three donor atoms, i.e., N, O, and S, are provided by a doubly deprotonated S-2-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene) dithiocarbazate ligand while the fourth donor, i.e., a thione-S, comes from the neutral form of the dithiocarbazate ligand. In the LH₂ ligand, an intramolecular hydroxy-O-H⋯N(imine) hydrogen bond is found. There is also an intra-ligand, charge assisted amine-N-H⋯O(phenoxide) hydrogen bond. A notable feature of the molecular packing is the formation of supramolecular chains sustained by π…π stacking interactions whereby the interacting rings are the five- and six-membered chelate and methoxybenzene rings. The chains are connected into a three-dimensional architecture by methyl-C-H⋯O(methoxy), methoxy-C-H⋯S(ester), and tolyl-C-H⋯π(tolyl) interactions. Full article

(This article belongs to the Section Structure Determination)

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4 pages, 801 KiB

Open AccessShort Note

8,18-Dithia-1,4,11,14-tetraazapentacyclo[11.7.0.0^3,11.0^5,9.0^15,19]icosa-3,5(9),6,13,15(19),16-hexaene-10,20-dione

by Vladimir A. Ogurtsov and Oleg A. Rakitin

Molbank 2019, 2019(2), M1056; https://doi.org/10.3390/M1056 - 13 Apr 2019

Cited by 1 | Viewed by 1567

Abstract

4H-3λ²-Thieno[3,2-d]pyrimidin-4-one derivatives are of interest as biologically active compounds. In this communication, 2-(chloromethyl)-4H-3λ²-thieno[3,2-d]pyrimidin-4-one (1) was investigated in the reaction with ammonia, potassium phthalimide, and other basic agents. The dimerization [...] Read more.

4H-3λ²-Thieno[3,2-d]pyrimidin-4-one derivatives are of interest as biologically active compounds. In this communication, 2-(chloromethyl)-4H-3λ²-thieno[3,2-d]pyrimidin-4-one (1) was investigated in the reaction with ammonia, potassium phthalimide, and other basic agents. The dimerization product—8,18-dithia-1,4,11,14-tetrazapentacyclo[11.7.0.0^3,11.0^5,9.0^15,19]icosa-3,5(9),6,13,15(19),16-hexaene-10,20-dione was formed in the reaction with potassium phthalimide in DMF, by heating at 110 °C for 5 h. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR, and IR spectroscopy, and mass-spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Molbank, Volume 2019, Issue 2 (June 2019) – 12 articles

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