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Molbank
Volume 2016
Issue 4
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Molbank, Volume 2016, Issue 4 (December 2016) – 14 articles

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1150 KiB  
Short Note
N-[2-(Cyclohexylamino)-2-oxoethyl]-N-(4-octyloxy)phenyl-prop-2-enamide
by Shimoga D. Ganesh, Nabanita Saha, Pavel Kucharczyk and Petr Sáha
Molbank 2016, 2016(4), M921; https://doi.org/10.3390/M921 - 13 Dec 2016
Viewed by 3352
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)
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Figure 1

334 KiB  
Short Note
3-(2-Hydroxyethyl)-2-methylbenzothiazolium Bromide
by Stela Minkovska, Nikolay Gadjev, Nikola Burdzhiev, Alexi Alexiev and Todor Deligeorgiev
Molbank 2016, 2016(4), M920; https://doi.org/10.3390/M920 - 09 Dec 2016
Viewed by 3194
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)
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Scheme 1

476 KiB  
Short Note
1,4-Dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde
by Kwang Min Ko and Sung-Gon Kim
Molbank 2016, 2016(4), M918; https://doi.org/10.3390/M918 - 30 Nov 2016
Viewed by 2621
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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815 KiB  
Short Note
3-Ethyl-2-(ethylimino)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylate Ethyl Ester
by Ge Meng, Mei Wang, Ya-Nan Cheng, Kai Chen, Jing Tong and Jie-He Zhang
Molbank 2016, 2016(4), M919; https://doi.org/10.3390/M919 - 29 Nov 2016
Viewed by 2903
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

1064 KiB  
Short Note
1,3,1′,3′-(Dinaphthalene-1,8-diyl)bisthiourea
by Fatma Aydin
Molbank 2016, 2016(4), M917; https://doi.org/10.3390/M917 - 28 Nov 2016
Cited by 1 | Viewed by 3112
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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1754 KiB  
Communication
2-C-Alkynyl and 2-C-cis-Alkenyl β-Mannosides with Acetal Protected γ-Aldehyde Functionality via 2-Uloside Alkynylation and Lindlar Hydrogenation
by Daniel Borowski, Melchior Menzel and Thomas Ziegler
Molbank 2016, 2016(4), M916; https://doi.org/10.3390/M916 - 11 Nov 2016
Cited by 2 | Viewed by 3738
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 [...] Read more.
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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476 KiB  
Short Note
(3,5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]methanone
by Rania B. Bakr and Ahmed B. M. Mehany
Molbank 2016, 2016(4), M915; https://doi.org/10.3390/M915 - 10 Nov 2016
Cited by 12 | Viewed by 3205
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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Graphical abstract

524 KiB  
Short Note
4,4′-Bis[4-(4′-hydroxyphenyl)phenylazo]diphenyl Ether
by Rahima Rahman, Asghari Gul and Zareen Akhter
Molbank 2016, 2016(4), M914; https://doi.org/10.3390/M914 - 27 Oct 2016
Cited by 2 | Viewed by 3298
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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Graphical abstract

1884 KiB  
Communication
4-Acetyl-2-hydroxy-2,5-dimethylfuran-3(2H)-one
by Chiaki Akazaki, Shun Kawabata and Hiroshi Nishino
Molbank 2016, 2016(4), M913; https://doi.org/10.3390/M913 - 20 Oct 2016
Cited by 3 | Viewed by 4393
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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Graphical abstract

540 KiB  
Short Note
Benzyl 2-((E)-Tosyliminomethyl)phenylcarbamate
by Kwang Min Ko and Sung-Gon Kim
Molbank 2016, 2016(4), M912; https://doi.org/10.3390/M912 - 17 Oct 2016
Viewed by 2918
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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Graphical abstract

1779 KiB  
Short Note
(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
by Rodrigo Abonia, Lorena Cabrera, Jairo Quiroga, Braulio Insuasty, Rodolfo Moreno-Fuquen and Alan R. Kennedy
Molbank 2016, 2016(4), M911; https://doi.org/10.3390/M911 - 15 Oct 2016
Cited by 3 | Viewed by 3393
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

1296 KiB  
Short Note
5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)methyl]-6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
by Assem Barakat, Hazem A. Ghabbour, Saleh Atef, Abdullah Mohammed Al-Majid, Mohammad Shahidul Islam and M. Ali
Molbank 2016, 2016(4), M910; https://doi.org/10.3390/M910 - 30 Sep 2016
Cited by 3 | Viewed by 3295
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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Graphical abstract

516 KiB  
Communication
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
by Camille D. Dago, Estelle Messé, Olivier Mignen, Christophe Brigaudeau, Yves-Alain Békro and Jean-Pierre Bazureau
Molbank 2016, 2016(4), M909; https://doi.org/10.3390/M909 - 22 Sep 2016
Cited by 2 | Viewed by 3342
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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Graphical abstract

1686 KiB  
Communication
Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition
by Yuki Ban, Yuichiro Ashida, Hidefumi Nakatsuji and Yoo Tanabe
Molbank 2016, 2016(4), M908; https://doi.org/10.3390/M908 - 22 Sep 2016
Cited by 2 | Viewed by 4365
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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