Studies on the derivatives of thiazoleacetic acid 2. syntheses and pharmacological analysis of 2 n aralkylidene and 2 n aralkyl derivatives of 2 amino 4 p chlorophenyl thiazole 5 acetic acid

Jakobiec, T.; Kowalczyk-Bronisz, S.H.; Stankiewicz, J.; Zawisza, T.; Glama, I.

Archivum Immunologiae et Therapiae Experimentalis 27(6): 795-814

1979


ISSN/ISBN: 0004-069X
Accession: 006515317

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Abstract
A number of 2-N-aralkylidene, 2-N-aralkyl and 2-N-aralkyl-.alpha.-sulphoderivatives of 2-amino-4-p-chlorophenylthiazole-5-acetic acid (I, R = H) and its methyl ester (I, R = CH3) were synthesized. As a result of condensation of methyl ester I with various aromatic aldehydes in boiling benzene solution, the Schiff-bases (anils) were obtained. After reduction with NaBH4 the compounds were transformed into amino esters. Esters heated with diluted aqueous solution of sodium hydroxide underwent selective hydrolysis giving the respective amino acids. Some Schiff bases reacted with aqueous alcoholic solution of sodium bisulphite to form a-sulfoderivatives. Several tests were performed in mice and rats to detect the antiinflammatory and immunosuppressive activity of the compounds. The pharmacological analysis allowed conclusions concerning the relationship between chemical structure and biological activity in this group of compounds to be made. The most efficacious immunosuppressive and antiinflammatory activity was exhibited by 2-aralkyl-.alpha.-sulfoderivatives.