Next Issue
Volume 2019, September
Previous Issue
Volume 2019, March

Table of Contents

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

  • Issues are regarded as officially published after their release is announced to the table of contents alert mailing list.
  • You may sign up for e-mail alerts to receive table of contents of newly released issues.
  • PDF is the official format for papers published in both, html and pdf forms. To view the papers in pdf format, click on the "PDF Full-text" link, and use the free Adobe Readerexternal link to open them.
Order results
Result details
Select all
Export citation of selected articles as:
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-)
Molbank 2019, 2019(2), M1067; https://doi.org/10.3390/M1067 - 25 Jun 2019
Viewed by 262
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)
Show Figures

Graphical abstract

Open AccessShort Note
α-d-Glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d-fructofuranoside]
Molbank 2019, 2019(2), M1066; https://doi.org/10.3390/M1066 - 16 Jun 2019
Viewed by 436
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)
Show Figures

Graphical abstract

Open AccessCommunication
N-Propargylation of Indolo-Triterpenoids and Their Application in Mannich Reaction
Molbank 2019, 2019(2), M1065; https://doi.org/10.3390/M1065 - 13 Jun 2019
Cited by 1 | Viewed by 284
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)
Show Figures

Graphical abstract

Open AccessShort Note
5,5′-Thiobis(3-methoxy-4H-1,2,6-thiadiazin-4-one)
Molbank 2019, 2019(2), M1064; https://doi.org/10.3390/M1064 - 09 Jun 2019
Viewed by 271
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)
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
Molbank 2019, 2019(2), M1063; https://doi.org/10.3390/M1063 - 04 Jun 2019
Viewed by 297
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)
Open AccessCommunication
(2S,5R)-2-Isopropyl-5-methylcyclohexanone Hydrazones
Molbank 2019, 2019(2), M1062; https://doi.org/10.3390/M1062 - 29 May 2019
Cited by 1 | Viewed by 321
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 3a3e 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)
Show Figures

Graphical abstract

Open AccessCommunication
4b,5,6,9-Tetrahydro-7H-dibenzo[c,e]pyrrolo[1,2-a]azepin-7-one
Molbank 2019, 2019(2), M1061; https://doi.org/10.3390/M1061 - 17 May 2019
Viewed by 386
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)
Show Figures

Graphical abstract

Open AccessCommunication
Synthesis of 1H-3-{4-[(3-Dimethylaminopropyl)aminomethyl]phenyl}-2-phenylindole and Evaluation of Its Antiprotozoal Activity
Molbank 2019, 2019(2), M1060; https://doi.org/10.3390/M1060 - 09 May 2019
Cited by 2 | Viewed by 301
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)
Open AccessShort Note
5-[(Z)-5-Chloro-2-oxoindolin-3-ylidene]-3-{(E)-[(4-hydroxyphenyl)imino]methyl}-2-thioxothiazolidin-4-one
Molbank 2019, 2019(2), M1059; https://doi.org/10.3390/M1059 - 06 May 2019
Viewed by 264
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)
Open AccessShort Note
(E)-N′-(4-Fluorobenzylidene)-5-methyl-2-(pyridin-3-yl)thiazole-4-carbohydrazide
Molbank 2019, 2019(2), M1058; https://doi.org/10.3390/M1058 - 02 May 2019
Viewed by 253
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)
Open AccessShort Note
A Ternary Nickel(II) Schiff Base Complex Containing Di-Anionic and Neutral Forms of a Dithiocarbazate Schiff Base
Molbank 2019, 2019(2), M1057; https://doi.org/10.3390/M1057 - 23 Apr 2019
Cited by 2 | Viewed by 277
Abstract
The title NiII 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 NiII 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)
Show Figures

Graphical abstract

Open AccessShort Note
8,18-Dithia-1,4,11,14-tetraazapentacyclo[11.7.0.03,11.05,9.015,19]icosa-3,5(9),6,13,15(19),16-hexaene-10,20-dione
Molbank 2019, 2019(2), M1056; https://doi.org/10.3390/M1056 - 13 Apr 2019
Viewed by 289
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[11.7.0.03,11.05,9.015,19]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)
Show Figures

Graphical abstract

Previous Issue
Back to TopTop