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Molbank, Volume 2016, Issue 4 (December 2016)

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Research

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Open AccessCommunication Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition
Molbank 2016, 2016(4), M908; doi:10.3390/M908
Received: 31 July 2016 / Revised: 19 September 2016 / Accepted: 19 September 2016 / Published: 22 September 2016
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Abstract
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed
[...] Read more.
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclo-condensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton. Full article
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Open AccessCommunication A Convenient Four-Step Synthesis of 1-{β-[3-(4-Methoxy-phenyl)Propoxy]-4-Methoxyphenethyl}-1H-Imidazole Hydrochloride as a Probing Tool for SOCE Assays
Molbank 2016, 2016(4), M909; doi:10.3390/M909
Received: 17 August 2016 / Revised: 16 September 2016 / Accepted: 19 September 2016 / Published: 22 September 2016
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Abstract
1-{β-[3-(4-Methoxy-phenyl)propoxy]-4-methoxyphenethyl}-1H-imidazole hydrochloride 7, or SKF-96365, was synthesized in four steps with an overall yield of 9%. The structure of 7 was confirmed by 1H-, 13C-NMR, HRMS, and elemental analysis. The intermediates 3 and 4 were also isolated and
[...] Read more.
1-{β-[3-(4-Methoxy-phenyl)propoxy]-4-methoxyphenethyl}-1H-imidazole hydrochloride 7, or SKF-96365, was synthesized in four steps with an overall yield of 9%. The structure of 7 was confirmed by 1H-, 13C-NMR, HRMS, and elemental analysis. The intermediates 3 and 4 were also isolated and characterized by 1H-, 13C-NMR, and HRMS. Full article
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Open AccessCommunication 4-Acetyl-2-hydroxy-2,5-dimethylfuran-3(2H)-one
Molbank 2016, 2016(4), M913; doi:10.3390/M913
Received: 7 September 2016 / Revised: 12 October 2016 / Accepted: 14 October 2016 / Published: 20 October 2016
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Abstract
The facile synthesis of 4-acetyl-2-hydroxy-2,5-dimethylfuran-3(2H)-one (4) was achieved by the Mn(OAc)3-mediated aerobic oxidation of 2,4-pentanedione or the direct reaction of Mn(acac)3 in AcOH-TFE at room temperature under a dried air stream. Full article
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Open AccessCommunication 2-C-Alkynyl and 2-C-cis-Alkenyl β-Mannosides with Acetal Protected γ-Aldehyde Functionality via 2-Uloside Alkynylation and Lindlar Hydrogenation
Molbank 2016, 2016(4), M916; doi:10.3390/M916
Received: 5 October 2016 / Revised: 3 November 2016 / Accepted: 7 November 2016 / Published: 11 November 2016
Cited by 1 | PDF Full-text (1754 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside was subjected to manno-selective ketone alkynylation with propiolaldehyde dibenzyl acetal, resulting in the formation of a 2-C-alkynyl β-mannoside bearing a γ-dibenzyl acetal functionality. Subsequent transacetalization of the acetal moiety with methanol and
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Benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside was subjected to manno-selective ketone alkynylation with propiolaldehyde dibenzyl acetal, resulting in the formation of a 2-C-alkynyl β-mannoside bearing a γ-dibenzyl acetal functionality. Subsequent transacetalization of the acetal moiety with methanol and 1,3-dihydroxypropane and acetylation of position 2, respectively, gave 4 different 2-C-alkynyl branched mannosides. Lindlar hydrogenation of the latter under optimized conditions in dimethylformamide afforded a series of 2-C-cis-alkenyl mannosides. X-ray molecular structures of benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-1,5-pyranoside and of the branched glycoside benzyl 3,4,6-tri-O-benzyl-2-C-((Z)-3,3-dibenzyloxyprop-1-en-1-yl)-β-d-mannopyranoside are reported. Full article
(This article belongs to the Section Organic Synthesis)
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Other

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Open AccessShort Note 5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)methyl]-6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
Molbank 2016, 2016(4), M910; doi:10.3390/M910
Received: 20 July 2016 / Revised: 20 August 2016 / Accepted: 28 September 2016 / Published: 30 September 2016
Cited by 1 | PDF Full-text (1296 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)-methyl]-6-hydroxy-1,3-di-methylpyrimidine-2,4(1H,3H)-dione 3 was synthesized via a multicomponent reaction. The Aldol–Michael addition reactions of N,N-dimethylbarbituric acid, cyclohexane-1,3-dione, and 3-fluorobenzaldehyde in aqueous solution gave the product in high yield. The molecular structure of the compound was confirmed by
[...] Read more.
5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)-methyl]-6-hydroxy-1,3-di-methylpyrimidine-2,4(1H,3H)-dione 3 was synthesized via a multicomponent reaction. The Aldol–Michael addition reactions of N,N-dimethylbarbituric acid, cyclohexane-1,3-dione, and 3-fluorobenzaldehyde in aqueous solution gave the product in high yield. The molecular structure of the compound was confirmed by spectroscopic methods and X-ray crystallography. The title compound (C19H19FN2O5·H2O) crystallizes in the Monoclinic form, P21/c, a = 7.8630 (5) Å, b = 20.0308 (13) Å, c = 11.3987 (8) Å, β = 104.274 (3)°, V = 1739.9 (2)° Å3, Z = 4, Rint = 0.117, wR(F2) = 0.124, T = 100 K. Full article
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Open AccessShort Note (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
Molbank 2016, 2016(4), M911; doi:10.3390/M911
Received: 14 September 2016 / Revised: 8 October 2016 / Accepted: 10 October 2016 / Published: 15 October 2016
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Abstract
The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis
[...] Read more.
The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis of dubamine and graveoline alkaloids. Single crystals of the title compound suitable for X-ray diffraction were grown via slow evaporation in ethanol at room temperature. A complete crystallographic study was performed in depth to unequivocally confirm its structure and determine some interesting supramolecular properties. The crystal structure of the title o-aminochalcone, C15H12ClNO, shows two molecules per asymmetric unit (Z′ = 2) and adopts an E configuration about the C=C double bond. In the title compound, the mean plane of the non-H atoms of the central chalcone fragment C—C(O)—C—C—C is as follows: [r.m.s. deviation = 0.0130 Å for A-B and 0.0043 for C-D molecules]. In the crystal, molecules are linked by N—H...N and C—H...O, hydrogen bonds forming edge-fused R66(46) rings parallel to (100). Additionally, N—H...O hydrogen bonds generate a three-dimensional network. Full article
(This article belongs to the Section Structure Determination)
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Figure 1

Open AccessShort Note Benzyl 2-((E)-Tosyliminomethyl)phenylcarbamate
Molbank 2016, 2016(4), M912; doi:10.3390/M912
Received: 8 September 2016 / Revised: 10 October 2016 / Accepted: 11 October 2016 / Published: 17 October 2016
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Abstract
Benzyl 2-((E)-tosyliminomethyl)penylcarbamate was prepared in good yield and characterized by the condensation reaction of benzyl 2-formylphenylcarbamate with p-toluenesulfonyl amine. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, IR and mass spectral data. Full article
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Open AccessShort Note 4,4′-Bis[4-(4′-hydroxyphenyl)phenylazo]diphenyl Ether
Molbank 2016, 2016(4), M914; doi:10.3390/M914
Received: 30 August 2016 / Revised: 20 October 2016 / Accepted: 20 October 2016 / Published: 27 October 2016
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Abstract
4,4′-Bis[4-(4′-hydroxyphenyl)phenylazo]diphenyl ether (3) was prepared by diazotization coupling of 4,4′-oxy dianiline (1) and biphenyl-4-ol (2). The synthesized compound (3) was characterized by elemental analysis, UV-Visible, FTIR and 1H-NMR (nuclear magnetic resonance) spectroscopic studies. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note (3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone
Molbank 2016, 2016(4), M915; doi:10.3390/M915
Received: 28 September 2016 / Revised: 29 October 2016 / Accepted: 8 November 2016 / Published: 10 November 2016
Cited by 1 | PDF Full-text (476 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In an attempt to enhance cytotoxic activity of pyrazolo[3,4-d]pyrimidine core, we synthesized (3,5-dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone (4) by reacting 4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)benzohydrazide (3) with acetylacetone. Antiproliferative activity of this compound was screened against breast
[...] Read more.
In an attempt to enhance cytotoxic activity of pyrazolo[3,4-d]pyrimidine core, we synthesized (3,5-dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone (4) by reacting 4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)benzohydrazide (3) with acetylacetone. Antiproliferative activity of this compound was screened against breast (MCF-7), colon (HCT-116), and liver (HEPG-2) cancer cell lines. The tested compound exhibited cytotoxic activity with IC50 = 5.00–32.52 μM. Moreover, inhibitory activity of this compound was evaluated against the epidermal growth factor receptor (EGFR), the fibroblast growth factor receptor (FGFR), the insulin receptor (IR), and the vascular endothelial growth factor receptor (VEGFR). This target compound showed potent inhibitory activity, especially against FGFR with IC50 = 5.18 μM. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note 1,3,1′,3′-(Dinaphthalene-1,8-diyl)bisthiourea
Molbank 2016, 2016(4), M917; doi:10.3390/M917
Received: 12 October 2016 / Revised: 7 November 2016 / Accepted: 15 November 2016 / Published: 28 November 2016
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Abstract
A new bisthiourea compound, 1,3,1′,3′-(dinaphthalene-1,8-diyl)bisthiourea, was synthesized. Its structure was characterized by elemental analysis, FT-IR and 1H-, 13C-NMR and MS spectroscopic techniques. The compound was found to selectively recognize fluoride anions among other halides as demonstrated by means of UV-vis absorption
[...] Read more.
A new bisthiourea compound, 1,3,1′,3′-(dinaphthalene-1,8-diyl)bisthiourea, was synthesized. Its structure was characterized by elemental analysis, FT-IR and 1H-, 13C-NMR and MS spectroscopic techniques. The compound was found to selectively recognize fluoride anions among other halides as demonstrated by means of UV-vis absorption spectroscopic date and the naked eye. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note 1,4-Dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde
Molbank 2016, 2016(4), M918; doi:10.3390/M918
Received: 26 October 2016 / Revised: 19 November 2016 / Accepted: 22 November 2016 / Published: 30 November 2016
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Abstract
An aza-Michael/Michael cascade reaction of 2-((E)-2-nitrovinyl)-N-tosylbenzenamine with 3-phenylpropiolaldehyde catalyzed by pyrrolidine has produced a new compound, 1,4-dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde. The structure of the newly synthesized compound was determined using 1H, 13C-NMR, IR, and mass spectral data. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note 3-Ethyl-2-(ethylimino)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylate Ethyl Ester
Molbank 2016, 2016(4), M919; doi:10.3390/M919
Received: 2 November 2016 / Revised: 22 November 2016 / Accepted: 22 November 2016 / Published: 29 November 2016
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Abstract
An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N′-diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method
[...] Read more.
An efficient procedure to obtain the new compound 1a from ethyl acetoacetate (2a), NBS and N,N′-diethylthiourea (4a) was reported. In comparison with the traditional method to synthesize its analogues, this efficient, catalyst-free, and one-pot synthetic method is facile. The work-up procedure is easy and gives the pure target compound under milder reaction conditions in a relatively high yield of 75%. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

Open AccessShort Note 3-(2-Hydroxyethyl)-2-methylbenzothiazolium Bromide
Molbank 2016, 2016(4), M920; doi:10.3390/M920
Received: 24 October 2016 / Revised: 29 November 2016 / Accepted: 5 December 2016 / Published: 9 December 2016
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Abstract
A novel method for the preparation of 3-(2-hydroxyethyl)-2-methylbenzothiazolium bromide was developed. It consists of heating of 2-methylbenzothiazole, 2-bromoethanol and ethoxyethanol for 2 h. On the next day the precipitate was filtered and air dried. Full article
(This article belongs to the Section Organic Synthesis)
Figures

Scheme 1

Open AccessShort Note N-[2-(Cyclohexylamino)-2-oxoethyl]-N-(4-octyloxy)phenyl-prop-2-enamide
Molbank 2016, 2016(4), M921; doi:10.3390/M921
Received: 1 November 2016 / Revised: 8 December 2016 / Accepted: 8 December 2016 / Published: 13 December 2016
PDF Full-text (1150 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
N-[2-(Cyclohexylamino)-2-oxoethyl]-N-(4-octyloxy)phenyl-prop-2-enamide was prepared in good yield by coupling of 4(octyloxy)aniline, Cyclohexyl isocyanide, paraformaldehyde and acrylic acid by multicomponent Ugi reaction, at room temperature. The structure of the newly synthesized tripeptoid derivative was well characterized using elemental analysis, FTIR, NMR and
[...] Read more.
N-[2-(Cyclohexylamino)-2-oxoethyl]-N-(4-octyloxy)phenyl-prop-2-enamide was prepared in good yield by coupling of 4(octyloxy)aniline, Cyclohexyl isocyanide, paraformaldehyde and acrylic acid by multicomponent Ugi reaction, at room temperature. The structure of the newly synthesized tripeptoid derivative was well characterized using elemental analysis, FTIR, NMR and mass spectral data. Full article
(This article belongs to the Section Organic Synthesis)
Figures

Figure 1

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