Nucleosides Bearing Quinazoline Moiety and Evaluation Their Antimicrobial effects

Kadhim, Mohammed Abed; EL-Hashash, Maher; Rizk, Samh

doi:10.37652/juaps.2022.174831

	Nucleosides Bearing Quinazoline Moiety and Evaluation Their Antimicrobial effects
Journal of University of Anbar for Pure Science
Article 3, Volume 16, Issue 1, 2022, Pages 13-19 PDF (754.55 K)
Document Type: Research Paper
DOI: 10.37652/juaps.2022.174831
Authors
Mohammed Abed Kadhim^* ¹; Maher EL-Hashash²; Samh Rizk³
¹Department of Chemistry , Faculty of Science, University of Anbar, Alanbar ,Iraq
²Department of Organic Chemistry , Faculty of Science, University of Ain Shams ,Cairo,
³Department of Organic Chemistry , Faculty of Science, University of Ain Shams ,Cairo, Egypt
Abstract
The present work describes convenient synthesis of the novel Schiff bases 4, 5 and 6 by reaction of each of the previously synthesized quinazolinones 1, 2 and 3 with p-methoxybenzaldehyde. [2+2] Cycloaddition Reaction of the former Schiff bases within phenylisothiocyanate affording azatedine derivatives 7 and 8. Also, the quinazolines 1 and 2 could be reacted with α-bromoglucose tetraacetate giving peracetylated N-glycosides of quinazolinones 9 and 10 which were then deacetylated to afford N-glycosylated quinazolinones 11 and 12 respectively. On the other hand, Dapsone was reacted with p-methoxyacetophenone to afford 4-[(4-aminophenyl) sulfonyl]-N-[(1E)-1-(4-methoxyphenyl)ethylidene]aniline 15 which was, in turn, reacted with 4-chloro-2-ethoxyquinazoline 16 affording Schiff base 17. The latter was reacted with 2-furoyl chloride affording Schiff base 18. The structures of the novel Schiff bases and N-glycosides were confirmed by the IR, 1H-NMR, 13C-NMR, MS and elemental analysis. The antimicrobial activity for these synthesized compounds could outline, the moderate activity was observed with new quinazoline compounds which proved to possess marked activity against E. coli, S. aureus and C. albicans. The strong activity has observed nearly with the most synthesized compounds .
Keywords
quinazolin-4(3H)-one; N-glycosylated quinazoline. Dapsone; Schiff base.Azatedine

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