Aseries of substituted 2-methylenehydrazino-4-aryl-4-oxobut-2-enoic acids and their anilides and esters were obtained using reactions of 4-aryl-2-hydroxy-4-oxobut-2-enoic acids and their amides and esters with benzophenone hydrazone, benzyl monohydrazone, and triphenylphosphazines. The methyl ester of 2-(1,2-diphenyl-2-oxoethylidenehydrazino)-4-(4-chlorophenyl)-4-oxobut-2-enoic acid was also synthesized by decyclization of 3-(1,2-diphenyl-2-oxoethylidenehydrazino)-5-(4-chlorophenyl)-3H-furan-2-one using methanol. The synthesized compounds exhibit moderate anti-inflammatory, analgesic, and antimicrobial activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Yu. S. Andreichikov, V. L. Gein, V. V. Zalesov, et al., in: Chemistry of Five-Membered 2,3-Dioxoheterocycles [in Russian], Yu. S. Andreichikov, ed., Izd. Perm. Univ., Perm (1994).
V. I. Saloutin, Ya. V. Burgart, and O. N. Chupakhin, Usp. Khim., 68(3), 227 – 239 (1999).
S. G. Perevalov, Ya. V. Burgart, V. I. Saloutin, et al., Usp. Khim., 70(11), 1039 – 1058 (2001).
V. O. Koz(minykh and E. N. Koz(minykh, Khim.-farm. Zh., 38(2), 10 – 20 (2004).
A. E. Rubtsov, R. R. Makhmudov, N. V. Kovylyaeva, et al., Khim.-farm. Zh., 36(11), 31 – 35 (2002).
S. Yu. Solodnikov, G. D. Mails, O. P. Krasnykh, et al., Khim.-farm. Zh., 36(5), 10 – 11 (2002).
A. E. Rubtsov and V. V. Zalesov, Zh. Org. Khim., 39(6), 918 – 923 (2003).
“Methodical Recommendations for Experimental Study of Nonsteroid Anti-inflammatory Compounds,” Pharmacological Committee, MZ USSR, Protocol No. 22 of Nov. 11, 1982, Moscow (1982).
V. V. Gatsura, Methods of Basic Pharmacological Studies of Biologically Active Compounds [in Russian], Meditsina, Moscow (1974), pp. 39 – 45.
V. P. Fisenko, ed., Handbook of Experimental (Preclinical) Study of New Pharmacological Compounds [in Russian], IIA Remedium, Moscow (2000), pp. 264 – 273.
V. B. Prozorovskii, M. P. Prozorovskaya, and V. I. Demchenko, Farmakol. Toksikol., 4, 497 – 502 (1978).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 43, No. 8, pp. 17 – 20, August, 2009.
deceased.
Rights and permissions
About this article
Cite this article
Pulina, N.A., Zalesov, V.V., Bystritskaya, O.A. et al. Synthesis and biological activity of substituted 4-aryl-2-methylenehydrazino-4-oxobut-2-enoic acids and their derivatives. Pharm Chem J 43, 444–447 (2009). https://doi.org/10.1007/s11094-009-0334-8
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-009-0334-8