Novel analogues of sydnone: synthesis, characterization and antibacterial evaluation.
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 alpha-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.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Abdulazis University, Geddah, Saudi Arabia.
Mohamed A
MA
Moustafa
Magdy M
MM
Gineinah
Magda N
MN
Nasr
Waleed A H
WA
Bayoumi
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D007202:Indicators and Reagents; D008826:Microbial Sensitivity Tests; D013558:Sydnones / Q000138:chemical synthesis* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D013558:Sydnones