Synthesis and antiinflammatory activity of novel 2,5-disubstituted thiophene derivatives

Authors

SAHAR BADR

DOI

10.3906/kim-1001-473

Abstract

New series of 2,5-disubstituted thiophenes were synthesized. Thiosemicarbazones 1a-b were reacted with various reagents, such as diethyl-2-bromomalonate, ethyl-2-chloroacetoacetate, thioglycolic acid, 4-substituted phenacyl bromides, and acetic anhydride, to afford heterocyclic substituted thiophene derivatives 2a-b, 3a-b, 4a-b, 5a-b, 6a-b, and 7a-b, respectively. Moreover, cyclization of the key intermediate 1b with chloroacetic acid yielded thiazolidine 9, which on reaction with appropriate aromatic aldehydes afforded the corresponding arylidene derivatives 10a-f. Finally, reaction of N^\-arylidene cyanoacetohydrazide 11 with sulfur and phenylisothiocyanate yielded thiazoline derivative 12, which on treatment with triethylorthoformate and acetic anhydride afforded thiazolo[4,5-d]pyrimidinone derivative 13. Some of the newly synthesized compounds showed promising antiinflammatory activity.

Keywords

Thiophenes, thiazoles, thiadiazoles, synthesis, antiinflammatory

First Page

131

Last Page

143

Recommended Citation

BADR, SAHAR (2011) "Synthesis and antiinflammatory activity of novel 2,5-disubstituted thiophene derivatives," Turkish Journal of Chemistry: Vol. 35: No. 1, Article 12. https://doi.org/10.3906/kim-1001-473
Available at: https://journals.tubitak.gov.tr/chem/vol35/iss1/12