A. Regiec, Z. Machoń, R. Międzybrodzki
Jul 1, 2006
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Influential Citations
23
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Quality indicators
Journal
Archiv der Pharmazie
Abstract
The synthesis and biological investigation of the series of amide and ester derivatives 10–20 of 5‐(4‐chlorobenzoyl)amino‐3‐methyl‐4‐isothiazolecarboxylic acid 5 are presented. Because the amide series of 5‐benzoylamino‐3‐methyl‐4‐isothiazolecarboxylic acid 2 has been studied extensively and from this series denotivir (vratizolin) 4 [1, 2] became the antiviral drug. The influence of exchanging the N‐benzoyl for a N‐(4‐chlorobenzoyl) group at position 5 of the isothiazole ring on the pharmacological activity of 5‐benzoylamino‐3‐methyl‐4‐isothiazolecarboxylic acid 2 derivatives is dealt with here. The effect of structure modifications in the carboxylic group of the 5‐(4‐chlorobenzoyl)amino‐3‐methyl‐4‐isothiazolecarboxylic acid 5 series of derivatives on their biological activity is discussed. Some of the tested 5‐(4‐chlorobenzoyl)amino‐3‐methyl‐4‐isothiazolecarboxylamides revealed significant anti‐inflammatory activity in carrageenan induced edema and air‐pouch inflammation tests. Physicochemical properties of 6‐(4‐chlorophenyl)‐3‐methylisothiazolo[5,4‐d]‐4H‐1,3‐oxazin‐4‐one 6 are described. Its use in the synthesis of isothiazole derivatives and its reactivity are also presented.