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Molbank, Volume 2019, Issue 4 (December 2019) – 17 articles

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Open AccessCommunication
(2Sp,4R,6R,8Sp)-4,6-Dimethyl-1-phenyl-diferroceno-1-phosphines
Molbank 2019, 2019(4), M1098; https://doi.org/10.3390/M1098 - 13 Dec 2019
Cited by 2 | Viewed by 744
Abstract
Ferrocene-based compounds are powerful asymmetric ligands usable for chemical catalysis. We present the synthesis of six new homochiral diferroceno cycles potentially useful as P,O-, P,N- or P,S-ligands. Due to the stereoconservative nature of the SN1 reaction at carbons adjacent to ferrocene [...] Read more.
Ferrocene-based compounds are powerful asymmetric ligands usable for chemical catalysis. We present the synthesis of six new homochiral diferroceno cycles potentially useful as P,O-, P,N- or P,S-ligands. Due to the stereoconservative nature of the SN1 reaction at carbons adjacent to ferrocene units, we obtained a single diastereomer of the 8-membered diferroceno[c,f]heterophosphocines in all cases. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessFeature PaperShort Note
5′-Chloro-5′-deoxy-2′,3′-O-isopropylidene-6-fluoro nebularine
Molbank 2019, 2019(4), M1097; https://doi.org/10.3390/M1097 - 13 Dec 2019
Cited by 1 | Viewed by 739
Abstract
In this paper, we report on the synthesis and spectroscopic characterization of the novel nucleoside 5′-chloro-5′-deoxy-2′,3′-O-isopropylidene-6-fluoro nebularine, obtained as a side product during the second step of the synthesis of 5′-fluoro-5′-deoxy-5-aminoimidazole-4-carboxamide-β-d-riboside (5′-F-AICAR), a non-phosphorylable analogue of 5-aminoimidazole-4-carboxamide-β-d-riboside (AICAR). Full article
(This article belongs to the Special Issue Molecules from Side Reactions) Printed Edition available
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Open AccessCommunication
Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone
Molbank 2019, 2019(4), M1096; https://doi.org/10.3390/M1096 - 10 Dec 2019
Cited by 1 | Viewed by 885
Abstract
2,3,5-Tri-O-benzyl- and 2,3,5-tri-O-methyl-d-ribono-γ-lactone were converted with (methoxyethoxymethoxy)methyl and benzyloxy tributylstannane into the corresponding protected d-psicoses as mixtures of anomers in 31%–72% yield. Treatment of 2,3,5-tri-O-methyl-l-ribono-γ-lactone with benzyloxy tributylstannane afforded the corresponding l [...] Read more.
2,3,5-Tri-O-benzyl- and 2,3,5-tri-O-methyl-d-ribono-γ-lactone were converted with (methoxyethoxymethoxy)methyl and benzyloxy tributylstannane into the corresponding protected d-psicoses as mixtures of anomers in 31%–72% yield. Treatment of 2,3,5-tri-O-methyl-l-ribono-γ-lactone with benzyloxy tributylstannane afforded the corresponding l-psicose derivative as an anomeric mixture in 72% yield. Both methylated psicoses were further converted into 1,2-O-isopropylidene-3,4,6-tri-O-methyl-d- and l-psicofuranosides, the respective α- and β-anomers of which could be separated and characterized. Full article
(This article belongs to the Special Issue Molecules from Side Reactions) Printed Edition available
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Open AccessCommunication
Pyridine-Imidazlolium Salts: Oxidatively Cleavage of N-C Bond via Nitration
Molbank 2019, 2019(4), M1095; https://doi.org/10.3390/M1095 - 23 Nov 2019
Cited by 1 | Viewed by 664
Abstract
Azaheterocycles derivatives with pyridine-imidazole skeleton are compounds of great value for medicinal chemistry. We report herein the nitration of 1,1′-(pyridine-2,6-diylbis(methylene))bis{3-[2-(4-nitrophenyl)-2-oxoethyl]-1H-imidazol-3-ium} bromide using a typical mixture of nitric and sulphuric acid. The nitration occur with the oxidative cleavage of N–C bond between [...] Read more.
Azaheterocycles derivatives with pyridine-imidazole skeleton are compounds of great value for medicinal chemistry. We report herein the nitration of 1,1′-(pyridine-2,6-diylbis(methylene))bis{3-[2-(4-nitrophenyl)-2-oxoethyl]-1H-imidazol-3-ium} bromide using a typical mixture of nitric and sulphuric acid. The nitration occur with the oxidative cleavage of N–C bond between imidazolium ring and methylene group. Full article
(This article belongs to the Special Issue Molecules from Side Reactions) Printed Edition available
Open AccessShort Note
Paenidigyamycin G: 1-Acetyl-2,4-dimethyl-3-phenethyl-1H-imidazol-3-ium
Molbank 2019, 2019(4), M1094; https://doi.org/10.3390/M1094 - 21 Nov 2019
Cited by 1 | Viewed by 673
Abstract
The Ghanaian Paenibacillus sp. DE2SH (GenBank Accession Number: MH091697) is a prolific producer of potent antiparasitic alkaloids. Further detailed study of the culture broth of this strain produced the compound Paenidigyamycin G (1), which is a derivative of the known antiparasitic [...] Read more.
The Ghanaian Paenibacillus sp. DE2SH (GenBank Accession Number: MH091697) is a prolific producer of potent antiparasitic alkaloids. Further detailed study of the culture broth of this strain produced the compound Paenidigyamycin G (1), which is a derivative of the known antiparasitic compound Paenidigyamycin A (2). Compound (1) was isolated on HPLC at tR ≈ 37.5 min and its structure determined by IR, UV, MS, 1D, and 2D-NMR data. Compound 1 produced weak to moderate antileishmanial and antitrypanosomal activity when tested against Leishmania donovani (Laveran and Mesnil) Ross (D10) and Trypanosoma brucei subsp. brucei strain GUTat 3.1 with IC50 = 115.41 and 28.75 μM, respectively. This result is interesting since the parent compound 2 is known to possess consistent and potent antiparasitic activity. However, 1 displayed a promising selectivity profile towards T. brucei subsp. brucei due to its relatively low toxicity against normal mouse macrophages RAW 264.7 cells (SI = 8.70). Given that compound 1 is also the main metabolite found in the hexane fraction of all extracts produced by Paenibacillus sp. DE2SH when it is co-cultured with other bacteria strains, it must possess some unique biological functions which should make it an excellent candidate for further biological activity screening in other bioassays. Full article
(This article belongs to the Section Natural Products)
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2,2′-((1,4-Dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene))bis(quinoline-3-carboxylic acid)
Molbank 2019, 2019(4), M1093; https://doi.org/10.3390/M1093 - 21 Nov 2019
Viewed by 828
Abstract
The title compound, 2,2′-((1,4-dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene))bis(quinoline-3-carboxylic acid) was synthesized from isoxazolo[3,4-b]quinolin-3(1H)-one and dimethyl acetylenedicarboxylate (DMAD) via a double aza-Michael addition followed by [1,3]-H shifts. The product was characterized by infrared and nuclear magnetic resonance spectroscopy, as well as elemental analysis and [...] Read more.
The title compound, 2,2′-((1,4-dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene))bis(quinoline-3-carboxylic acid) was synthesized from isoxazolo[3,4-b]quinolin-3(1H)-one and dimethyl acetylenedicarboxylate (DMAD) via a double aza-Michael addition followed by [1,3]-H shifts. The product was characterized by infrared and nuclear magnetic resonance spectroscopy, as well as elemental analysis and high-resolution mass spectrometry (HRMS). The proposed reaction mechanism was rationalized by density functional theory (DFT) calculations. Full article
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Open AccessShort Note
1,1,4,7-Tetramethyldecahydro-1H-cyclopropa[e]azulen-7-ol from the Stembark Chisocheton pentandrus
Molbank 2019, 2019(4), M1092; https://doi.org/10.3390/M1092 - 20 Nov 2019
Viewed by 657
Abstract
A new aromadendrane-type sesquiterpenoid, namely dehydrosphatulenol (1), has been isolated from the stembark of Chisocheton pentandrus. The chemical structure of 1 was characterized on the basis of spectroscopic evidences including mainly one dimension and two dimension Nuclear Magnetic Resonance, and [...] Read more.
A new aromadendrane-type sesquiterpenoid, namely dehydrosphatulenol (1), has been isolated from the stembark of Chisocheton pentandrus. The chemical structure of 1 was characterized on the basis of spectroscopic evidences including mainly one dimension and two dimension Nuclear Magnetic Resonance, and Mass Spectroscopy as well as through a comparison with those related compounds previously reported. Full article
(This article belongs to the Section Natural Products)
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Open AccessShort Note
8-(Pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane
Molbank 2019, 2019(4), M1091; https://doi.org/10.3390/M1091 - 20 Nov 2019
Cited by 1 | Viewed by 586
Abstract
Heptasulfur imides substituted by hereterocycle may be of interest as biologically active compounds. In this communication, the reaction of pyrimidin-2-amine 1 with disulfur dichloride was carefully investigated to give 8-(pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane in good yield. The structure of the newly synthesized compound was established by [...] Read more.
Heptasulfur imides substituted by hereterocycle may be of interest as biologically active compounds. In this communication, the reaction of pyrimidin-2-amine 1 with disulfur dichloride was carefully investigated to give 8-(pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane in good yield. 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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Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2S)-2-[(1R)-1-(methylamino)-ethyl]]ferrocene-aminal
Molbank 2019, 2019(4), M1090; https://doi.org/10.3390/M1090 - 19 Nov 2019
Cited by 3 | Viewed by 747
Abstract
In the course of an ongoing synthetic project, we observed an unprecedented reactivity of N-methyl groups in bis(N,N-dimethylaminoethylferrocenyl)phenylphosphinesulfide upon treatment with manganese dioxide (MnO2). The intramolecular course of this reaction resulted in the formation of an [...] Read more.
In the course of an ongoing synthetic project, we observed an unprecedented reactivity of N-methyl groups in bis(N,N-dimethylaminoethylferrocenyl)phenylphosphinesulfide upon treatment with manganese dioxide (MnO2). The intramolecular course of this reaction resulted in the formation of an unexpected homochiral diaza macrocycle. The target structure was accessible in two steps from known N,N-dimethylaminoethylferrocene. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note
1-Octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium Bis(trifluoromethane)sulfonimide
Molbank 2019, 2019(4), M1089; https://doi.org/10.3390/M1089 - 19 Nov 2019
Viewed by 694
Abstract
The title compound 1-octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium bis(trifluoromethane)sulfonimide was prepared in three steps. This asymmetrical dicationic ionic liquid (ADIL) is composed of two different positively charged head groups (1-octylimidazolium and methylpyrrolidinium cations), which are linked through a propyl alkyl chain and by two bis(trifluoromethane)sulfonimide anions. The [...] Read more.
The title compound 1-octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium bis(trifluoromethane)sulfonimide was prepared in three steps. This asymmetrical dicationic ionic liquid (ADIL) is composed of two different positively charged head groups (1-octylimidazolium and methylpyrrolidinium cations), which are linked through a propyl alkyl chain and by two bis(trifluoromethane)sulfonimide anions. The final ADIL was obtained by a simple metathesis reaction of the corresponding dibromide ionic liquid, in turn prepared by alkylation of 3-(3-bromopropyl)-1-propylimidazolium bromide. The ADIL structure and those of its precursors were confirmed through NMR and infrared spectroscopy, and the thermal properties of all compounds were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Density, solubility, and viscosity were measured for the prepared compounds. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note
3-(3,4-Dimethoxyphenyl)-5-(2-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole
Molbank 2019, 2019(4), M1088; https://doi.org/10.3390/M1088 - 12 Nov 2019
Cited by 1 | Viewed by 776
Abstract
A new analogue of fluorinated pyrazoline (compound 1) has been synthesized via one-pot three-component reaction in a sealed-vessel reactor, Monowave 50. The structure of compound 1 has been established by spectroscopy analysis, including UV, FT-IR, HRMS, 1H and 13C NMR [...] Read more.
A new analogue of fluorinated pyrazoline (compound 1) has been synthesized via one-pot three-component reaction in a sealed-vessel reactor, Monowave 50. The structure of compound 1 has been established by spectroscopy analysis, including UV, FT-IR, HRMS, 1H and 13C NMR spectroscopy. Based on the in silico studies, this compound showed a good potential as an inhibitor for dengue virus type 2 (DEN2) NS2B/NS3 serine protease and can be used as a reference in the next design of an antidengue virus. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note
6-Bromo-N-(2-methyl-2H-benzo[d][1,2,3]triazol-5-yl)quinolin-4-amine
Molbank 2019, 2019(4), M1087; https://doi.org/10.3390/M1087 - 27 Oct 2019
Cited by 4 | Viewed by 879
Abstract
We describe a straightforward synthesis of the title compound, incorporating a relatively rare 2-methyl-2H-1,2,3-triazole heterocylic motif as a potential kinase inhibitor motif. The small molecule crystal structure has been resolved, revealing an interesting packing arrangement and overall conformation. We also performed [...] Read more.
We describe a straightforward synthesis of the title compound, incorporating a relatively rare 2-methyl-2H-1,2,3-triazole heterocylic motif as a potential kinase inhibitor motif. The small molecule crystal structure has been resolved, revealing an interesting packing arrangement and overall conformation. We also performed routine characterization with 1H/13C-NMR and liquid chromatography (LC) and high-resolution mass spectra (HRMS). Full article
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Open AccessFeature PaperCommunication
Synthesis of 2-Cyanopyrimidines
Molbank 2019, 2019(4), M1086; https://doi.org/10.3390/M1086 - 22 Oct 2019
Cited by 3 | Viewed by 614
Abstract
4,6-Dichloro-2-(methylthio)pyrimidine (7) was converted to 4-chloro-6-methoxy-2-(methylthio)pyrimidine (15) and 4,6-dimethoxy-2-(methylthio)pyrimidine (14). Chlorination of the latter with N-chlorosuccinimide (NCS) affords 5-chloro-4,6-dimethoxy-2-(methylthio)pyrimidine (16) in 56% yield. Both methylthiopyrimidines 15 and 14 were converted in two steps to [...] Read more.
4,6-Dichloro-2-(methylthio)pyrimidine (7) was converted to 4-chloro-6-methoxy-2-(methylthio)pyrimidine (15) and 4,6-dimethoxy-2-(methylthio)pyrimidine (14). Chlorination of the latter with N-chlorosuccinimide (NCS) affords 5-chloro-4,6-dimethoxy-2-(methylthio)pyrimidine (16) in 56% yield. Both methylthiopyrimidines 15 and 14 were converted in two steps to 4-chloro-6-methoxypyrimidine-2-carbonitrile (13) and 4,6-dimethoxypyrimidine-2-carbonitrile (12), respectively, after oxidation to sulfones and displacement of the sulfinate group with KCN. 4,6-Dimethoxypyrimidine-2-carbonitrile (12) was chlorinated with NCS to give 5-chloro-4,6-dimethoxypyrimidine-2-carbonitrile (10) in 53% yield. All new compounds were fully characterized. Full article
Open AccessCommunication
Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies
Molbank 2019, 2019(4), M1085; https://doi.org/10.3390/M1085 - 14 Oct 2019
Cited by 2 | Viewed by 652
Abstract
A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, 1H NMR, 13C NMR, LC/MS [...] Read more.
A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, 1H NMR, 13C NMR, LC/MS and single crystal X-ray diffraction. UV/Vis and IR spectra of compounds are described. The presence of a strong intramolecular hydrogen bond between the hydroxy group and the carbonyl oxygen atom of the ester group in methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate is shown. The crystal structure of product was stabilized through intermolecular hydrogen bonds. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Open AccessCommunication
Reactions of Polychlorinated Pyrimidines with DABCO
Molbank 2019, 2019(4), M1084; https://doi.org/10.3390/M1084 - 14 Oct 2019
Cited by 2 | Viewed by 644
Abstract
The reaction of 2,4,5,6-tetrachloropyrimidine (4) and 4,5,6-trichloropyrimidine-2-carbonitrile (1) with DABCO (1 equiv.), in MeCN, at ca. 20 °C gives 2,4,5-trichloro-6-[4-(2-chloroethyl)piperazin-1-yl]pyrimidine (5) and 4,5-dichloro-6-[4-(2-chloroethyl)piperazin-1-yl]pyrimidine-2-carbonitrile (6) in 42% and 52% yields, respectively. The new compounds were fully characterized. Full article
Open AccessShort Note
3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione
Molbank 2019, 2019(4), M1083; https://doi.org/10.3390/M1083 - 03 Oct 2019
Viewed by 591
Abstract
The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human [...] Read more.
The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human blood cell. The title compound 5, subjected to in vitro activities, showed that it is cytotoxic with an IC50 of 42.30 µM and a good anti-inflammatory agent. The docking results against cyclin dependent kinase 2 (CDK2) (PDB ID: 3QQK) gave insights on its inhibitory activity. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessShort Note
2-{[Bis(propan-2-yl)carbamothioyl]sulfanyl}acetic acid
Molbank 2019, 2019(4), M1082; https://doi.org/10.3390/M1082 - 20 Sep 2019
Cited by 1 | Viewed by 564
Abstract
The title compound, (iPr)2NC(=S)SCH2C(=O)OH (1), was synthesized by conventional methods and its X-ray crystal structure was determined by X-ray crystallography. The compound was further characterized by analytical, IR, UV, 1D NMR (1H and 13C{ [...] Read more.
The title compound, (iPr)2NC(=S)SCH2C(=O)OH (1), was synthesized by conventional methods and its X-ray crystal structure was determined by X-ray crystallography. The compound was further characterized by analytical, IR, UV, 1D NMR (1H and 13C{1H}), and 2D NMR (DEPT-135) spectroscopy, and density functional theory (DFT) methods. X-ray crystallography on 1 confirms the formulation and reveals a nearly orthogonal relationship between the planar NCS2 and C2O2 residues. In the crystal, hydroxyl-O–H⋯O(carbonyl) hydrogen bonds lead dimers via an eight-membered {⋯OCOH}2 ring. Full article
(This article belongs to the Section Structure Determination)
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