Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological Activity

In this work, a series of new Nucleoside analogues (D-galactopyranose linked to oxepanebenzimidazole moiety) was synthesized via multisteps synthesis. The first step involved preparation of two benzimidazoles 2-styrylbenzimidazole and 2-(phenyl ethynyl) benzimidazole via reaction of phenylenediamine...

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Main Author: Baghdad Science Journal
Format: Article
Language:English
Published: University of Baghdad, College of Science for Women 2016-09-01
Series:مجلة بغداد للعلوم
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Online Access:http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/2298
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author Baghdad Science Journal
author_facet Baghdad Science Journal
author_sort Baghdad Science Journal
collection DOAJ
description In this work, a series of new Nucleoside analogues (D-galactopyranose linked to oxepanebenzimidazole moiety) was synthesized via multisteps synthesis. The first step involved preparation of two benzimidazoles 2-styrylbenzimidazole and 2-(phenyl ethynyl) benzimidazole via reaction of phenylenediamine with cinnamic acid or ?-phenyl propiolic acid. Electrophilic addition of the prepared benzimidazoles by three anhydrides in the second step afforded (4-6) and (14-16) which in turn were treated with 1,2,3,4-di-O-isopropylidene galactopyranose in the third step to afford a series of the desirable protected nucleoside analogues (7-9) ,(17-19)which after hydrolysis in methanolic sodium methoxidein the fourth step afforded the free nucleoside analogues (10-12) and (20-22) .The synthesized compounds were identified by FT-IR and some of them by 1H-NMR and13C-NMR. The synthesized oxepane nucleoside analogues were screened for their antibacterial activity against three types of bacteria including Staphylococcusaureus ,Bacillus(gram positive) andE.coli (gram negative) bacteria repectively.
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spelling doaj-art-7c827eae6d7042abb8dba5daf5535f652025-08-20T02:52:26ZengUniversity of Baghdad, College of Science for Womenمجلة بغداد للعلوم2078-86652411-79862016-09-0113310.21123/bsj.13.3.531-546Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological ActivityBaghdad Science JournalIn this work, a series of new Nucleoside analogues (D-galactopyranose linked to oxepanebenzimidazole moiety) was synthesized via multisteps synthesis. The first step involved preparation of two benzimidazoles 2-styrylbenzimidazole and 2-(phenyl ethynyl) benzimidazole via reaction of phenylenediamine with cinnamic acid or ?-phenyl propiolic acid. Electrophilic addition of the prepared benzimidazoles by three anhydrides in the second step afforded (4-6) and (14-16) which in turn were treated with 1,2,3,4-di-O-isopropylidene galactopyranose in the third step to afford a series of the desirable protected nucleoside analogues (7-9) ,(17-19)which after hydrolysis in methanolic sodium methoxidein the fourth step afforded the free nucleoside analogues (10-12) and (20-22) .The synthesized compounds were identified by FT-IR and some of them by 1H-NMR and13C-NMR. The synthesized oxepane nucleoside analogues were screened for their antibacterial activity against three types of bacteria including Staphylococcusaureus ,Bacillus(gram positive) andE.coli (gram negative) bacteria repectively.http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/2298"Nucleoside, oxepane nucleoside, isopropyledenegalactopyranose"
spellingShingle Baghdad Science Journal
Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological Activity
مجلة بغداد للعلوم
"Nucleoside, oxepane nucleoside, isopropyledenegalactopyranose"
title Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological Activity
title_full Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological Activity
title_fullStr Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological Activity
title_full_unstemmed Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological Activity
title_short Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological Activity
title_sort synthesis of some new nucleoside analogues containing seven membered ring and studying their biological activity
topic "Nucleoside, oxepane nucleoside, isopropyledenegalactopyranose"
url http://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/2298
work_keys_str_mv AT baghdadsciencejournal synthesisofsomenewnucleosideanaloguescontainingsevenmemberedringandstudyingtheirbiologicalactivity