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SYNTHESIS OF ACYCLOVIR AND HBG ANALOGUES HAVING NICOTINONITRILE AND ITS 2-METHYLOXY 1,2,3-TRIAZOLE
Faculty
Science
Year:
2011
Type of Publication:
Article
Pages:
340-352
Authors:
Moustafa, Ahmed H, El-Sayed, Hassan A, Haikal, Abd El-Fattah Z, El Ashry, El Sayed H
DOI:
10.1080/15257770.2011.582850
Journal:
NUCLEOSIDES NUCLEOTIDES \& NUCLEIC ACIDS TAYLOR \& FRANCIS INC
Volume:
30
Research Area:
Biochemistry \& Molecular Biology
ISSN
ISI:000294553500002
Keywords :
Pyridin-2(1H)-one, acyclonucleosides, 1, 2, 3-triazole, [}3+2] cycloaddition
Abstract:
Reaction of pyridin-2(1H)-one 1 with 4-bromobutylacetate (2), (2-acetoxyethoxy)methyl bromide (3) gave the corresponding nicotinonitrile O-acyclonucleosides, 4 and 5, respectively. Deacetylation of 4 and 5 gave the corresponding deprotected acyclonucleosides 6 and 7, respectively. Treatment of pyridin-2(1H)-one 1 with 1,3-dichloropropan-2-ol (8), epichlorohydrin (10) and allyl bromide (12) gave the corresponding nicotinonitrile O-acyclonucleosides 9, 11, and 13, respectively. Furthermore, reaction of pyridin-2(1H)-one 1 with the propargyl bromide (14) gave the corresponding 2-O-propargyl derivative 15, which was reacted via {[}3+2] cycloaddition with 4-azidobutyl acetate (16) and {[}(2-acetoxyethoxy)methyl]azide (17) to give the corresponding 1,2,3-triazole derivatives 18 and 19, respectively. The structures of the new synthesized compounds were characterized by using IR, (1)H, (13)C NMR spectra, and microanalysis. Selected members of these compounds were screened for antibacterial activity.
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