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Novel Analogues of Sydnone: Synthesis, Characterization and Antibacterial Evaluation
Author(s) -
Moustafa Mohamed A.,
Gineinah Magdy M.,
Nasr Magda N.,
Bayoumi Waleed A. H.
Publication year - 2004
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200300847
Subject(s) - sydnone , characterization (materials science) , chemistry , combinatorial chemistry , antibacterial activity , antibacterial agent , chemical synthesis , stereochemistry , organic chemistry , nanotechnology , materials science , bacteria , antibiotics , in vitro , biochemistry , biology , ring (chemistry) , genetics
Abstract New sydnone derivatives bearing a substituted phenyl ring at the 3‐position have been synthesized. Two separate series of 3‐(carboxyphenyl)sydnone derivatives have been prepared by cyclization of the corresponding N ‐nitroso‐ N ‐(carboxyphenyl)‐glycine 3 . The obtained 3‐(carboxyphenyl)sydnones 4 were subjected to a series of different chemical reactions on the carboxylic acid group. Compound 5 , the potassium salt of 4a , was reacted with α‐chloroacetanilide derivatives 6 to give the corresponding esters 7 . On the other hand, the acid hydrazide 9 was condensed with different aromatic aldehydes to give the corresponding arylidene derivatives 10 . The synthesized compounds were tested for their antibacterial activities against both gram‐positive and gram‐negative organisms. Some of the test compounds exhibited high activity; among them, 10d is considered to be a lead compound possessing high broad‐spectrum antibacterial activity.