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Molecules 2010, 15(7), 4711-4721; doi:10.3390/molecules15074711

Article

Synthesis of Some New Pyridine-2,6-carboxamide-derived Schiff Bases as Potential Antimicrobial Agents

Mohamed A. Al-Omar and Abd El-Galil E. Amr*

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia

* Author to whom correspondence should be addressed.

Received: 13 June 2010; in revised form: 30 June 2010 / Accepted: 1 July 2010 / Published: 6 July 2010

Download PDF Full-Text [179 KB, uploaded 6 July 2010 10:31 CEST]

Abstract: A series of pyridine-bridged 2,6-bis-carboxamide Schiff's bases has been prepared starting from 2,6-pyridinedicarbonyl dichloride (1) and L-alanine or 2-methyl-alanine methyl ester.The coupling of acid chloride 1 with L-alanine methyl ester hydrochloride -or 2-methylalanine methyl ester hydrochloride gave the corresponding 2,6-bis-carboxamide pyridine methyl esters 2a,b.Hydrazonolysis of 2 with hydrazine hydrate afforded the corresponding bis-hydrazides 3a,b. Treatment of 3a,b with appropriate aromatic or heterocyclic aldehydes afforded the corresponding pyridine- bridged 2,6-bis-carboxamide Schiff's bases 4a-f and 5a-f, respectively. The newly synthesized compounds 2-5 were screened for their bactericidal and fungicidal activities. Many of the obtained compounds exhibited significant antimicrobial activity, comparable to streptomycin and fusidic acid, which were used as reference antibiotic drugs.

Keywords: 2,6-pyridinedicarbonyl dichloride; pyridine-2,6-carboxamides; Schiff's base; antimicrobial activity

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