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Molbank, Volume 2018, Issue 3 (September 2018)

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Open AccessShort Note O-Methyl m-Tolylcarbamothioate
Molbank 2018, 2018(3), M1020; https://doi.org/10.3390/M1020
Received: 4 September 2018 / Revised: 13 September 2018 / Accepted: 13 September 2018 / Published: 15 September 2018
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Abstract
The synthesis, spectroscopic, and crystallographic characterisation of the title compound, O-methyl m-tolylcarbamothioate, MeOC(=S)N(H)(m-tolyl) (1), are described. The crystallographic study confirms the structure determined by spectroscopy and shows the presence of the thioamide tautomer, a syn-disposition of
[...] Read more.
The synthesis, spectroscopic, and crystallographic characterisation of the title compound, O-methyl m-tolylcarbamothioate, MeOC(=S)N(H)(m-tolyl) (1), are described. The crystallographic study confirms the structure determined by spectroscopy and shows the presence of the thioamide tautomer, a syn-disposition of the thione-S and thioamide-N-H atoms and, in the crystal, thioamide-N-HS(thione) hydrogen bonding leading to an eight-membered {HNCS}2 synthon. Full article
(This article belongs to the Section Structure Determination)
Open AccessShort Note (E)-1-(2′,4′-Dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one
Molbank 2018, 2018(3), M1019; https://doi.org/10.3390/M1019
Received: 27 August 2018 / Revised: 10 September 2018 / Accepted: 12 September 2018 / Published: 13 September 2018
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Abstract
Thiazole and chalcone motifs are of research interest to medicinal chemists due to their array of synthetic and biological utility. Hence, in the present study we intended to prepare (E)-1-(2′,4′-dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one (3c) containing both these scaffolds. The compound 3c was
[...] Read more.
Thiazole and chalcone motifs are of research interest to medicinal chemists due to their array of synthetic and biological utility. Hence, in the present study we intended to prepare (E)-1-(2′,4′-dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one (3c) containing both these scaffolds. The compound 3c was synthesized by the acid-catalyzed condensation of 2,4-dimethyl-5-acetylthiazole with 2,4-difluorobenzaldehyde. Purification and characterization of the compound were carried out by recrystallization and spectral techniques including UV, IR, 1H-NMR, 13C-NMR, Mass spectrometry and X-ray powdered diffractometry. The molecule 3c was successfully synthesized, purified, and characterized. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessFeature PaperShort Note 5-Amino-3-(diethylamino)-5H-benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine 1,1-Dioxide
Molbank 2018, 2018(3), M1018; https://doi.org/10.3390/M1018
Received: 20 August 2018 / Revised: 6 September 2018 / Accepted: 6 September 2018 / Published: 11 September 2018
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Abstract
In the quest for discovery of novel bioactive molecules, new heterocyclic ring systems provide templates for exploration of uncharted chemical space. Herein, we describe the synthesis of a new benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine derivative from readily available 1,2-diaminobenzimidazole and N,N-diethyl-N
[...] Read more.
In the quest for discovery of novel bioactive molecules, new heterocyclic ring systems provide templates for exploration of uncharted chemical space. Herein, we describe the synthesis of a new benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine derivative from readily available 1,2-diaminobenzimidazole and N,N-diethyl-N′-chlorosulfonyl chloroformamidine. The product structure, confirmed by X-ray crystallography, bears an exocyclic NH2 group, which should enable synthesis of an extended range of derivatives of this unusual scaffold. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Open AccessFeature PaperShort Note (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one
Molbank 2018, 2018(3), M1017; https://doi.org/10.3390/M1017
Received: 27 July 2018 / Revised: 22 August 2018 / Accepted: 27 August 2018 / Published: 31 August 2018
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Abstract
(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one has been synthesized for the first time by the enantiospecific oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1,1-diphenylbutan-1-ol. The cyclocarbonylation reaction was carried out at 100 °C in 1,2-dimethoxyethane (DME) as the solvent for 15 h, under 20 atm of
[...] Read more.
(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one has been synthesized for the first time by the enantiospecific oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1,1-diphenylbutan-1-ol. The cyclocarbonylation reaction was carried out at 100 °C in 1,2-dimethoxyethane (DME) as the solvent for 15 h, under 20 atm of a 4:1 mixture of CO–air and in the presence of the catalytic system PdI2/KI (substrate:KI:PdI2 molar ratio = 100:10:1), to give the oxazolidinone derivative in 81% isolated yield. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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Graphical abstract

Open AccessShort Note (1R,5S)-6-(4-Methyl-2-oxo-2,5-dihydrofuran-3-yl)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one
Molbank 2018, 2018(3), M1016; https://doi.org/10.3390/M1016
Received: 11 August 2018 / Revised: 25 August 2018 / Accepted: 28 August 2018 / Published: 30 August 2018
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Abstract
Efficient large-scale and feasible industrial synthesis of the 1-oxacephem core structure from 6-aminopenicillanic acid (6-APA) has been reported for several decades. Via the industrial synthesis route, a byproduct (compound 9) containing a butenolide unit was purified and characterized by NMR and HRMS
[...] Read more.
Efficient large-scale and feasible industrial synthesis of the 1-oxacephem core structure from 6-aminopenicillanic acid (6-APA) has been reported for several decades. Via the industrial synthesis route, a byproduct (compound 9) containing a butenolide unit was purified and characterized by NMR and HRMS in this work. It is worth noting that compound 9 is an entirely new compound. Additionally, a plausible mechanism and effects on the formation of 9 by different Lewis acids were proposed. The discovery of compound 9 could improve the purity of this feasible industrial synthesis and provide considerable cost savings. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessFeature PaperShort Note (3-Ammonio-2,2-dimethyl-propyl)carbamate Dihydrate
Molbank 2018, 2018(3), M1015; https://doi.org/10.3390/M1015
Received: 16 July 2018 / Revised: 26 August 2018 / Accepted: 27 August 2018 / Published: 29 August 2018
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Abstract
(3-Ammonio-2,2-dimethylpropyl)carbamate dihydrate was synthesised. The title compound was characterised by single crystal X-ray diffraction and IR-/Raman-spectroscopy. It has been demonstrated that a mixture of dilute acetic acid and 2,2-dimethyl-1,3-diaminopropane is able to capture CO2 spontaneously from the atmosphere. An intramolecular hydrogen bond
[...] Read more.
(3-Ammonio-2,2-dimethylpropyl)carbamate dihydrate was synthesised. The title compound was characterised by single crystal X-ray diffraction and IR-/Raman-spectroscopy. It has been demonstrated that a mixture of dilute acetic acid and 2,2-dimethyl-1,3-diaminopropane is able to capture CO2 spontaneously from the atmosphere. An intramolecular hydrogen bond stabilises the conformation of the ylide-type title molecule. Intermolecular hydrogen bonds between all moieties connect them to a strand-type chain structure. Full article
(This article belongs to the Section Structure Determination)
Open AccessFeature PaperShort Note 1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine
Molbank 2018, 2018(3), M1014; https://doi.org/10.3390/M1014
Received: 14 August 2018 / Revised: 22 August 2018 / Accepted: 23 August 2018 / Published: 24 August 2018
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Abstract
1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine (3) has been successfully synthesized by reacting p-toluic hydrazide (1) and glycine (2) via the polyphosphoric acid condensation route. The course of the reaction was found to be high yielding (87%) and the title compound
[...] Read more.
1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine (3) has been successfully synthesized by reacting p-toluic hydrazide (1) and glycine (2) via the polyphosphoric acid condensation route. The course of the reaction was found to be high yielding (87%) and the title compound was spectroscopically characterized by UV-Vis, FTIR, DSC, 13C/1H-NMR, and sass spectrometric techniques. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Graphical abstract

Open AccessShort Note 5-[3-(4-Bromophenyl)-1-(2,5-dimethoxyphenyl)-3-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-tri-one
Molbank 2018, 2018(3), M1013; https://doi.org/10.3390/M1013
Received: 2 August 2018 / Revised: 19 August 2018 / Accepted: 20 August 2018 / Published: 23 August 2018
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Abstract
The title compound was prepared by a two-step reaction. The first step was the formation of a chalcone derivative using Claisen–Schmidt condensation, which was followed by the Michael addition of the formed chalcone with 1,3-dimethylbarbituric acid. The structure of the prepared compound was
[...] Read more.
The title compound was prepared by a two-step reaction. The first step was the formation of a chalcone derivative using Claisen–Schmidt condensation, which was followed by the Michael addition of the formed chalcone with 1,3-dimethylbarbituric acid. The structure of the prepared compound was established by spectral data: FTIR, HRESIMS, 1H- and 13C-NMR. Full article
(This article belongs to the Special Issue Molecules from Catalytic Processes)
Open AccessShort Note N-(4-Bromophenyl)methoxycarbothioamide
Molbank 2018, 2018(3), M1012; https://doi.org/10.3390/M1012
Received: 26 July 2018 / Revised: 13 August 2018 / Accepted: 13 August 2018 / Published: 17 August 2018
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Abstract
The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the
[...] Read more.
The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the asymmetric unit of 1. The C‒S and C‒N bond lengths confirm the presence of the thioamide tautomer. The thione-S and amide-N‒H atoms are syn, enabling the formation of amide-N‒HS(thione) hydrogen bonds between the two independent molecules that generates a two-molecule aggregate via an eight-membered {HNCS}2 synthon. The aggregates are connected into a three-dimensional architecture via weak intermolecular interactions, including Brπ(4-bromophenyl), Sπ(4-bromophenyl), and weak BrS halogen bonding contacts. The overall molecular conformation, thioamide tautomer, and the presence of amide-N‒HS(thione) hydrogen bonding in the crystal conform with expectation for this class of compound. Full article
(This article belongs to the Section Structure Determination)
Open AccessShort Note 3-(3,5-Difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
Molbank 2018, 2018(3), M1011; https://doi.org/10.3390/M1011
Received: 14 July 2018 / Revised: 30 July 2018 / Accepted: 30 July 2018 / Published: 1 August 2018
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Abstract
Vilsmeier–Haack reaction of (E)-1-[1-(3,5-difluorophenyl)ethylidene]-2-phenylhydrazine (1) using dimethyl formamide in excess of phosphorus oxychloride by conventional method, resulted in the synthesis of the title compound 3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4- carbaldehyde (2) in good yield and high purity. Structure characterization
[...] Read more.
Vilsmeier–Haack reaction of (E)-1-[1-(3,5-difluorophenyl)ethylidene]-2-phenylhydrazine (1) using dimethyl formamide in excess of phosphorus oxychloride by conventional method, resulted in the synthesis of the title compound 3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4- carbaldehyde (2) in good yield and high purity. Structure characterization of the title compound was done by IR, 1H-NMR, 13C-NMR and HRMS spectral analysis. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessCommunication Benzyl (R)-2-(Acetylthio)Propanoate: A Promising Sulfur Isoster of (R)-Lactic Acid and Ester Precursors
Molbank 2018, 2018(3), M1010; https://doi.org/10.3390/M1010
Received: 6 July 2018 / Revised: 22 July 2018 / Accepted: 24 July 2018 / Published: 29 July 2018
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Abstract
In this paper, an accessible chiral pool synthesis of benzyl (R)-2-(acetylthio)propanoate (acetylthiolactate), which is less odorous than the methyl or ethyl analogue, was performed through a clean SN2 displacement reaction using available AcSK with tris[2-(2-methoxyethoxy)]ethylamine (TDA-1), starting from commercially
[...] Read more.
In this paper, an accessible chiral pool synthesis of benzyl (R)-2-(acetylthio)propanoate (acetylthiolactate), which is less odorous than the methyl or ethyl analogue, was performed through a clean SN2 displacement reaction using available AcSK with tris[2-(2-methoxyethoxy)]ethylamine (TDA-1), starting from commercially available benzyl (S)-lactate in 76%, 94% ee (2 steps). Deprotection of the acetyl group using N,N-dimethylethylenediamine afforded benzyl (R)-2-sulfanylpropanoate in 93% yield with 90% ee. These two sulfur-containing benzyl esters were sufficiently odorless to be purified by column chromatography. Direct HPLC analysis was applied to determine the enantiomeric excess without thiazolidin-4-one derivatizations. A complementary debenzylation of benzyl (R)-2-(acetylthio)propanoate was also performed using HBr/AcOH to afford (R)-2-(acetylthio)propanoic acid without critical racemization in 92% yield with 92% ee. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note 2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid
Molbank 2018, 2018(3), M1009; https://doi.org/10.3390/M1009
Received: 5 July 2018 / Revised: 23 July 2018 / Accepted: 27 July 2018 / Published: 29 July 2018
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Abstract
Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as
[...] Read more.
Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as the catalyst. The structure of the title compound is determined by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectral data. In order to determine the molecular interactions with the bacterial enzyme, the title compound is further docked into the active site of the MurB protein of Staphylococcus aureus (PDB ID: 1HSK). The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. The compound is also evaluated for its antioxidant property by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging assay. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

Open AccessShort Note N-[2-(1H-Indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide
Molbank 2018, 2018(3), M1008; https://doi.org/10.3390/M1008
Received: 10 July 2018 / Revised: 24 July 2018 / Accepted: 24 July 2018 / Published: 25 July 2018
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Abstract
N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13
[...] Read more.
N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13C-NMR spectroscopy. To investigate the potential of compound 2 to act as antitubercular agent, it was docked against the enoyl reductase (InhA) enzyme of Mycobacterium tuberculosis. The docking pose and non-covalent interactions gave insights on its plausible inhibitory action. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Graphical abstract

Open AccessShort Note 5,7-Dihydroxy-3,6-Dimethoxy-3′,4′-Methylendioxyflavone
Molbank 2018, 2018(3), M1007; https://doi.org/10.3390/M1007
Received: 25 June 2018 / Revised: 17 July 2018 / Accepted: 19 July 2018 / Published: 23 July 2018
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Abstract
A new flavonoid derivative, namely 5,7-dihydroxy-3,6-dimethoxy-3′,4′-methylenedioxyflavone (1), was isolated from the leaves of Melicope glabra (Blume) T.G. Hartley. The structure of 1 was elucidated based on their UV, IR, HRESIMS, and 1D and 2D NMR spectral data. Full article
(This article belongs to the Section Natural Products)
Open AccessFeature PaperShort Note Quercetin-3-oleate
Molbank 2018, 2018(3), M1006; https://doi.org/10.3390/M1006
Received: 27 June 2018 / Revised: 16 July 2018 / Accepted: 19 July 2018 / Published: 20 July 2018
PDF Full-text (900 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Polyphenols are well-known health promoting agents, but they have some limitations due to their spontaneous oxidation. This evidence has limited their use as drugs in recent years. In this field, several chemical modifications have been proposed to overcome these restrictions; among these, esterification
[...] Read more.
Polyphenols are well-known health promoting agents, but they have some limitations due to their spontaneous oxidation. This evidence has limited their use as drugs in recent years. In this field, several chemical modifications have been proposed to overcome these restrictions; among these, esterification seems to be the preferred modification. Ester derivatives may be able to reduce the bioavailability problems connected to polyphenols. On the other hand, the presence of esterase enzymes in the body guarantees ester hydrolysis, which in turn frees the two molecules that make it up. Lipase-catalyzed esterifications gave birth to several derivatives of flavonoids glycosides, in green conditions. In this short paper, pancreatic porcine lipase was firstly used as a cheap bio-catalyst, to synthesize oleoyl derivatives of quercetin in aglycone form. The results demonstrated how the enzyme is able to promote a regioselective acylation on C-3 position, with high yields and easy purification processes. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

Open AccessShort Note 1-(4-Hexylbenzoyl)-3-methylthiourea
Molbank 2018, 2018(3), M1005; https://doi.org/10.3390/M1005
Received: 12 June 2018 / Revised: 5 July 2018 / Accepted: 6 July 2018 / Published: 9 July 2018
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Abstract
The 1-(4-hexylbenzoyl)-3-methylthiourea compound has been successfully synthesized by reacting 4-hexylbenzoyl chloride and 1-methylthiourea via the reflux method using a triethylamine catalyst. The 1-(4-hexylbenzoyl)-3-methylthiourea compound was identified by UV-visible, FT-IR, 13C/1H-NMR and Mass spectrophotometry. From the activity test on four cancer
[...] Read more.
The 1-(4-hexylbenzoyl)-3-methylthiourea compound has been successfully synthesized by reacting 4-hexylbenzoyl chloride and 1-methylthiourea via the reflux method using a triethylamine catalyst. The 1-(4-hexylbenzoyl)-3-methylthiourea compound was identified by UV-visible, FT-IR, 13C/1H-NMR and Mass spectrophotometry. From the activity test on four cancer cell lines (HeLa, T47D, WiDr and MCF7 cell), it could be seen that it had better activity on four cancer cells than the control, hydroxyurea. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note 5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
Molbank 2018, 2018(3), M1004; https://doi.org/10.3390/M1004
Received: 18 June 2018 / Revised: 6 July 2018 / Accepted: 6 July 2018 / Published: 9 July 2018
PDF Full-text (777 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Natural and semi-synthetic compounds are being studied as novel phosphodiesterase 5 (PDE5) inhibitors for the treatment of erectile dysfunction, pulmonary hypertension, and lower urinary symptoms. Maclura pomifera is a source of flavonoids, one of the main classes of molecules investigated for these purposes.
[...] Read more.
Natural and semi-synthetic compounds are being studied as novel phosphodiesterase 5 (PDE5) inhibitors for the treatment of erectile dysfunction, pulmonary hypertension, and lower urinary symptoms. Maclura pomifera is a source of flavonoids, one of the main classes of molecules investigated for these purposes. The extraction of the natural isoflavone osajin and its modification to obtain a semi-synthetic derivative are described in this short note. 1H and 13C-nuclear magnetic resonance spectroscopy (NMR), mass spectrometry, high-performance liquid chromatography (HPLC) and spectroscopic characterization of the title compound are also hereby provided. Two-dimensional (2D) nuclear Overhauser effect spectroscopy (NOESY) NMR, supported by in silico conformational studies, was used to achieve a complete assignment of the proton signals, assessing the correct chemical structure of the compound. Heteronuclear single quantum coherence spectroscopy (HSQC) and heteronuclear multiple bond correlation (HMBC) NMR experiments were performed to assign 13C chemical shifts. Calculated chemical properties and preliminary in silico docking suggest that this molecule might be a promising candidate as PDE5 inhibitor. Full article
(This article belongs to the Section Natural Products)
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Graphical abstract

Open AccessShort Note 3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide]
Molbank 2018, 2018(3), M1003; https://doi.org/10.3390/M1003
Received: 22 June 2018 / Revised: 2 July 2018 / Accepted: 3 July 2018 / Published: 5 July 2018
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Abstract
The nitramino derivatives of furoxans are of specific interest as precursors for the preparation of high energy salts with nitrogen-rich cations. In this communication, the 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was prepared via nitration of available 4,4′-diamino-3,3′-diazenofuroxan; the best yield of the target compound was achieved
[...] Read more.
The nitramino derivatives of furoxans are of specific interest as precursors for the preparation of high energy salts with nitrogen-rich cations. In this communication, the 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was prepared via nitration of available 4,4′-diamino-3,3′-diazenofuroxan; the best yield of the target compound was achieved under the action of nitrating system HNO3/(CF3CO)2O in molar ratio 15:3 in CCl4 at −5 °C. The structure of 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was confirmed by means of 1H, 13C,14N-NMR, IR spectroscopy and high resolution mass spectra (HRMS). Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Graphical abstract

Open AccessCommunication 2-[2-Methyl-5-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide
Molbank 2018, 2018(3), 1002; https://doi.org/10.3390/M1002
Received: 16 June 2018 / Revised: 26 June 2018 / Accepted: 26 June 2018 / Published: 28 June 2018
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Abstract
We synthesized 2-[2-methyl-5-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide 4 as a novel compound derived from the indibulin and combretastatin scaffolds, which are known anti-mitotic agents, using a multistep reaction. We tested its cytotoxic activity against three breast cancer cell lines, namely, MCF-7, T47-D,
[...] Read more.
We synthesized 2-[2-methyl-5-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide 4 as a novel compound derived from the indibulin and combretastatin scaffolds, which are known anti-mitotic agents, using a multistep reaction. We tested its cytotoxic activity against three breast cancer cell lines, namely, MCF-7, T47-D, and MDA-MB 231 as well as normal cell line NIH-3T3, by 3-(4,5-dimethylthiazoyl-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The biological activity results showed good cytotoxicity on cancerous cell lines (IC50 value 27.7–39.2 µM) and low toxicity on normal cell line (NIH-3T3, IC50 value > 100 µM). Full article
(This article belongs to the Special Issue Heterocycles)
Open AccessShort Note (E)-3-[3-(2-Butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one
Molbank 2018, 2018(3), 1001; https://doi.org/10.3390/M1001
Received: 25 May 2018 / Revised: 15 June 2018 / Accepted: 18 June 2018 / Published: 21 June 2018
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Abstract
The coumarinyl-quinolinylchalcone hybrid (E)-3-[3-(2-butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one 3b was prepared in good yield from a Claisen-Schmidt condensation reaction between 3-acetyl-4-hydroxy-2H-chromen-2-one 1 and 2-butoxyquinoline-3-carbaldehyde 2 in methanol at reflux and catalyzed by KOH pellets. The structure of the synthesized compound 3b
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The coumarinyl-quinolinylchalcone hybrid (E)-3-[3-(2-butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one 3b was prepared in good yield from a Claisen-Schmidt condensation reaction between 3-acetyl-4-hydroxy-2H-chromen-2-one 1 and 2-butoxyquinoline-3-carbaldehyde 2 in methanol at reflux and catalyzed by KOH pellets. The structure of the synthesized compound 3b was fully confirmed by FTIR-ATR, (1D and 2D) NMR experiments, EIMS and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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