Cyclocondensation of 4-(3,4-dimethoxybenzyl)heptan-4-ol with N-substituted cyanoacetamide was used to synthesize (3,3-dipropyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2(2H)-ylidene)acetamides. The hydrochlorides of the resulting enaminoamides exist in the imino form. All hydrochlorides displayed analgesic effects in the hotplate test at the level of sodium metamizole, and the most active were the amide with the N-substituted 2-(3,4-dimethyoxyphenyl)ethyl radical, which had greater levels of analgesic activity than metamizole and nimesulide. Many of the resulting amides displayed anti-inflammatory effects in a carragheenan model which were comparable in magnitude to those of sodium metamizole.
Similar content being viewed by others
References
L. V. Anikina, Yu. B. Vikharev, V. A. Safin, et al., Khim.-Farm. Zh., 36(2), 19 – 23 (2002); Pharm. Chem. J., 36(2), 18 – 22 (2002).
V. A. Glushkov, L. V. Anikina, Yu. B. Vikharev, et al., Khim.-Farm. Zh., 39(10), 27 – 29 (2005); Pharm. Chem. J., 39(10), 533 – 536 (2005).
Yu. B. Vikharev, Yu. V. Shklyaev, L. V. Anikina, et al., Khim.-Farm. Zh., 39(8), 13 – 15 (2005); Pharm. Chem. J., 39(8), 405 – 408 (2005).
L. V. Anikina, Yu. B. Vikharev, A. A. Gorbunov, and Yu. V. Shklyaev, Khim.-Farm. Zh., 47(8), 23 – 25 (2013); Pharm. Chem. J., 47(8), 419 – 421 (2013).
O. V. Surikova, E. S. Limanskii, G. A. Aleksandrova, et al., Khim.-Farm. Zh., 47(4), 20 – 23 (2013); Pharm. Chem. J., 47(4), 198 – 201 (2013).
O. V. Surikova, A. S. Yusov, R. R. Makhmudov, and A. G. Mikhailovskii, Khim.-Farm. Zh., 51(1), 20 – 22 (2017); Pharm. Chem. J., 51(1), 18 – 21 (2017).
O. V. Surikova, A. G. Mikhailovskii, B. Ya. Syropyatov, et al., Khim.-Farm. Zh., 51(1), 23 – 25 (2017); Pharm. Chem. J., 51(1), 22 – 25 (2017).
N. B. Eddy and D. Leimbach, J. Pharmacol. Exp. Ther., 107(3), 385 – 393 (1953).
F. P. Trinus, B. M. Klebanov, V. I. Kondratyuk, Methodolgoical Guidelines for Experimental Studies of Nonsteroidal Anti-inflammatory Pharmacological Substances [in Russian], USSR Ministry of Health, Moscow (1983).
Guidelines for Preclinical Studies of Drugs [in Russian], A. N. Mironov and N. D. Bunyatyan (eds.), Grif i K, Moscow (2012), part 1.
V. B. Prozorovskii, M. P. Prozorovskaya, and V. M. Demchenko, armakol. Toksikol., 41(4), 497 – 502 (1978).
K. K. Sidorov, in: Toxicology of Novel Industrial Substances [in Russian], issue 13, Moscow (1973), pp. 47 – 51.
Ya. A. Sigidin, G. Ya. Shvarts, A. P. Arzamastsev, and S. S. Liberman, Treatment of the Inflammatory Process: Experimental and Clinical Pharmacology of Anti-inflammatory Drugs [in Russian], Meditsina, Moscow (1988).
A. V. Piskarev, V. S. Nesterenko, and S. I. Suminov, Farmakol. Toksikol., 38(1), 48 – 54 (1973).
V. E. Kolla and B. Ya. Syropyatov, Doses of Drugs and Chemical Compounds for Laboratory Animals [in Russian], Meditsina, Moscow (1998), p. 155.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 53, No. 1, pp. 36 – 40, January, 2019.
Rights and permissions
About this article
Cite this article
Yusov, A.S., Chashchina, S.V., Mikhailovskii, A.G. et al. Synthesis and Analgesic and Anti-Inflammatory Activities of (3,3-Dipropyl-6,7-Dimethoxy-3,4-Dihydroisoquinolin-1(2H)-Ylidene)-Acetamide Hydrochlorides. Pharm Chem J 53, 35–39 (2019). https://doi.org/10.1007/s11094-019-01951-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-019-01951-y