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Synthesis, antitumor and antimicrobial activities of 4-(4-chlorophenyl)-3-cyano-2-(beta-O-glycosyloxy)-6-(thien-2-yl)-nicotin onitrile
Faculty
Science
Year:
2011
Type of Publication:
Article
Pages:
2948-2954
Authors:
Moustafa, Ahmed H, El-Sayed, Hassan A, Haikal, Abd El-Fattah Z, Abu-El-Halawa, Rajab, El Ashry, El Sayed H
DOI:
10.1016/j.ejmech.2011.04.019
Journal:
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Volume:
46
Research Area:
Pharmacology \& Pharmacy
ISSN
ISI:000291895200032
Keywords :
3-Cyanopyridin-2(1H)-one, Nicotinonitrile 2-O-glycosides/ribosides, 2-O-Lactoside, Microwave, Antitumor, Antimicrobial activity
Abstract:
4-(4-Chlorophenyl)-3-cyano-6-(thien-2-yl)-1H-pyridin-2-one (2) was obtained by reaction of 2-acetyl thiophene with 4-chlorobenzaldehyde and ethyl cyanoacetate in presence of ammonium acetate or by the reaction of alpha,beta-unsaturated compound 1 with ethyl cyanoacetate in the presence of ammonium acetate. 4-(4-Chlorophenyl)-2-(2',3',4',6'-tetra-O-acetyl-beta-D-gluco/galactopyr anosyloxy)-6-(thien-2-yl) nicotinonitrile (5a and 5b), riboside 11, xyloside 12 and lactoside 16 were prepared by the reaction of 2 with glycosyl/galactosyl/xylosyl/lactosyl bromide and peracetylated xylose/ribose under the conventional and microwave irradiation methods. The reaction has regioselectively gave the O-glycosides and not the N-glycosides. The glycosides 5a,b, riboside 11, xyloside 12 and lactoside 16 were deacetylated in the presence of Et3N/MeOH and few drops of water to give 7a,b, 13, 14 and 17. The structure of the new synthesized compounds was confirmed by using IR, H-1, C-13 NMR spectra and microanalysis. Selected members of these compounds were screened for antitumor and antibacterial activity. (C) 2011 Elsevier Masson SAS. All rights reserved.
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