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Molbank, Volume 2019, Issue 3 (September 2019)

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Open AccessShort Note
4-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole
Molbank 2019, 2019(3), M1074; https://doi.org/10.3390/M1074
Received: 30 June 2019 / Revised: 12 July 2019 / Accepted: 16 July 2019 / Published: 19 July 2019
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Abstract
The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was established on the basis [...] Read more.
The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was established on the basis of NMR spectroscopy (1H, 13C), MS data and elemental analysis. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessShort Note
2,6-Bis[4-(4-butylphenyl)-1H-1,2,3-triazol-1-yl]-9-dodecyl-9H-purine
Molbank 2019, 2019(3), M1073; https://doi.org/10.3390/M1073
Received: 21 June 2019 / Accepted: 12 July 2019 / Published: 14 July 2019
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Abstract
Target 2,6-bis[4-(4-butylphenyl)-1H-1,2,3-triazol-1-yl]-9-dodecyl-9H-purine has been prepared via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction between 2,6-diazido-9-dodecyl-9H-purine and 4-n-butyl(phenylacetylene) in a 29% yield. The obtained compound was fully characterized by NMR, IR and HRMS. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessFeature PaperShort Note
1-(Imidazo[1,2-a]pyridin-1-ium-1-yl)-2,3,4-trioxocyclobutan-1-ide
Molbank 2019, 2019(3), M1072; https://doi.org/10.3390/M1072
Received: 5 June 2019 / Revised: 8 July 2019 / Accepted: 9 July 2019 / Published: 12 July 2019
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Abstract
1-(Imidazo[1,2-a]pyridin-1-ium-1-yl)-2,3,4-trioxocyclobutan-1-ide was obtained by reaction of squaric acid with imidazo[1,2-a]pyridine in acetic anhydride. Full article
(This article belongs to the Section Structure Determination)
Open AccessShort Note
4,4″-Dichloro-4′-(2-thienyl)-2,2′:6′,2″-terpyridine
Molbank 2019, 2019(3), M1071; https://doi.org/10.3390/M1071
Received: 25 June 2019 / Revised: 3 July 2019 / Accepted: 4 July 2019 / Published: 9 July 2019
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Abstract
A new thiophene-substituted terpyridine derivative has been prepared and characterized. This ligand features a thiophene heterocycle (as an electrochemically polymerizable unit) as well as two chlorine atoms for further functionalization. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note
N-(Isobutyl)-3,4-methylenedioxy Cinnamoyl Amide
Molbank 2019, 2019(3), M1070; https://doi.org/10.3390/M1070
Received: 19 June 2019 / Revised: 2 July 2019 / Accepted: 3 July 2019 / Published: 5 July 2019
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Abstract
The plant Zanthoxylum zanthoxyloides (Lam.) Zepern. & Timler is one of the most important medicinal species of the genus Zanthoxylum on the African continent. It is used in the treatment and management of parasitic diseases in sub-Saharan Africa. These properties have inspired scientists [...] Read more.
The plant Zanthoxylum zanthoxyloides (Lam.) Zepern. & Timler is one of the most important medicinal species of the genus Zanthoxylum on the African continent. It is used in the treatment and management of parasitic diseases in sub-Saharan Africa. These properties have inspired scientists to investigate species within the genus for bioactive compounds. However, a study, which details a spectroscopic, spectrometric and bioactivity guided extraction and isolation of antiparasitic compounds from the genus Zanthoxylum is currently non-existent. Tortozanthoxylamide (1), which is a derivative of the known compound armatamide was isolated from Z. zanthoxyloides and the full structure determined using UV, IR, 1D/2D-NMR and high-resolution liquid chromatography tandem mass spectrometry (HRESI-LC-MS) data. When tested against Trypanosoma brucei subsp. brucei, the parasite responsible for animal African trypanosomiasis in sub-Saharan Africa, 1 (IC50 7.78 µM) was just four times less active than the commercially available drug diminazene aceturate (IC50 1.88 µM). Diminazene aceturate is a potent drug for the treatment of animal African trypanosomiasis. Tortozanthoxylamide (1) exhibits a significant antitrypanosomal activity through remarkable alteration of the cell cycle in T. brucei subsp. brucei, but it is selectively non-toxic to mouse macrophages RAW 264.7 cell lines. This suggests that 1 may be considered as a scaffold for the further development of natural antitrypanosomal compounds. Full article
(This article belongs to the Section Natural Products)
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Open AccessShort Note
[Dicyclohexyl(sulfanylidene)-λ5-phosphanyl]methanol
Molbank 2019, 2019(3), M1069; https://doi.org/10.3390/M1069
Received: 18 June 2019 / Revised: 27 June 2019 / Accepted: 28 June 2019 / Published: 2 July 2019
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Abstract
The title compound, [dicyclohexyl(sulfanylidene)-λ5-phosphanyl]methanol, Cy2P(=S)CH2OH (1), was obtained from the reaction between [Cy2P(CH2OH)2]Cl with one molar equivalent of NaOH and an excess of elemental sulfur (powdered). Characterization was by [...] Read more.
The title compound, [dicyclohexyl(sulfanylidene)-λ5-phosphanyl]methanol, Cy2P(=S)CH2OH (1), was obtained from the reaction between [Cy2P(CH2OH)2]Cl with one molar equivalent of NaOH and an excess of elemental sulfur (powdered). Characterization was by a single-crystal X-ray structure determination as well as IR, and 1D-NMR (1H, 13C{1H}, 31P{1H}), and 2D-NMR (DEPT-135 and HSQC) spectroscopy, ESI mass spectrometry, and elemental analysis. X-ray crystallography on Compound 1 shows the phosphorus atom to be tetrahedrally coordinated within a non-symmetric C3S donor set but with relatively minor distortions from the ideal geometry. In the molecular packing, hydroxyl-O–H⋯S(thione) hydrogen bonds led to supramolecular helical chains along the b-axis direction. Full article
(This article belongs to the Section Structure Determination)
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Open AccessShort Note
6R/S-deutero-α-d-mannopyranoside 1-phosphate
Molbank 2019, 2019(3), M1068; https://doi.org/10.3390/M1068
Received: 3 June 2019 / Revised: 19 June 2019 / Accepted: 24 June 2019 / Published: 27 June 2019
PDF Full-text (367 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
6R/S-deutero-α-d-mannopyranoside 1-phosphate was synthesised from a C6 aldehydic mannose thioglycoside donor in four steps. Using NaBD4 as the reductant, isotopic enrichment at C6 was achieved and the resultant C6-deuterated material was converted through to the glycosyl [...] Read more.
6R/S-deutero-α-d-mannopyranoside 1-phosphate was synthesised from a C6 aldehydic mannose thioglycoside donor in four steps. Using NaBD4 as the reductant, isotopic enrichment at C6 was achieved and the resultant C6-deuterated material was converted through to the glycosyl 1-phosphate using a protection/glycosylation/deprotection sequence. The product was fully characterised by 1H, 13C, 31P and 2D NMR, alongside MS analysis. Full article
(This article belongs to the Special Issue Organic Synthesis of Carbohydrates)
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Molbank EISSN 1422-8599 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
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