Synthesis and Antinociceptive Activity of Substituted 2-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thiophene-2-ylamino)-4-oxobut-2-enoates
I. A. Gorbunovaa, Yu. O. Sharavyevaa, R. R. Makhmudova, D. A. Shipilovskikha, b, V. M. Shadrinc, N. A. Pulinac, and S. A. Shipilovskikha, d, *
aPerm State University, Perm, 614990 Russia
bPerm National Research Polytechnic University, Perm, 614990 Russia
cPerm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation, Perm, 614990 Russia
dITMO University, St. Petersburg, 197101 Russia
email: *s.shipilovskikh@metalab.ifmo.ru
Received 13 June, 2022
Abstract—
A method was proposed for the synthesis of substituted 2-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-4-oxobut-2-enoates containing a nitrile substituent in the thiophene ring by reacting the corresponding 3-thienylimino-3H-furan-2-ones with primary alcohols. The antinociceptive activity and acute toxicity of the obtained compounds were investigated. It was found that the substituted esters have pronounced antinociceptive activity and low toxicity. According to the classification of toxicity of drugs, the obtained substituted of 2-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-4-oxobut-2-enoates belong to the V class toxicity.
Keywords:
Gewald thiophenes,
2,4-dioxobutane acids,
3-(thiophene-2-yl)imino-3H-furan-2-ones,
antinociceptive activity,
toxicity
DOI: 10.1134/S1070363222100048