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.
Highlights
In our previous work, we have reported that certain of substituted pyridine and Schiff base derivatives as antimicrobial, anti-inflammatory and anticancer agents [1,2,3,4,5,6]
In continuation of our interest in the chemical and pharmacological properties of disubstituted pyridine derivatives [17,18,19,20], we report the synthesis and antimicrobial activities of a new series of hydrazides and their corresponding N2,N6-bis(1-oxo-1-(2(substituted-benzylidene)-hydrazinyl)propan-2-yl)pyridine-2,6-di-carboxamide derivatives (Schiff's bases)
L-Alanine and/or 2-methylalanine methyl esters were initially coupled with 2,6-pyridinedicarbonyl dichloride (1) [21] to give the corresponding 2,6-bis-carboxamide pyridine methyl esters 2a,b
Summary
We have reported that certain of substituted pyridine and Schiff base derivatives as antimicrobial, anti-inflammatory and anticancer agents [1,2,3,4,5,6]. Schiff base and other heterocyclic derivatives were reported to possess diverse biological activities, such as antibacterial. Several substituted pyridines and their derivatives were reported to exhibit significant antimicrobial [14], anti-inflammatory [15] and anticancer activities [16]. In continuation of our interest in the chemical and pharmacological properties of disubstituted pyridine derivatives [17,18,19,20], we report the synthesis and antimicrobial activities of a new series of hydrazides and their corresponding N2,N6-bis(1-oxo-1-(2(substituted-benzylidene)-hydrazinyl)propan-2-yl)pyridine-2,6-di-carboxamide derivatives (Schiff's bases)
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