Analgesic and Antidepressant Activity of 8-Substituted Harmine Derivatives

Seidakhmetova R.B. Amanzhan A. Shults E.E. Goldaeva K.V. Adekenov S.M. Berillo D.
July 2022 Springer

Chemistry of Heterocyclic Compounds
2022 #58 Issue 6-7 324 - 332 pp.

[Figure not available: see fulltext.] The present study describes the synthesis of a novel type of harmine derivatives, containing substituent at the C-8 position and their physicochemical characterization by FTIR, NMR, and elemental analysis. Computer simulation of the interaction of harmine and its derivatives (Z)-8-(1-hydrazonoethyl)-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole and 8-{(Z)-1-[(Z)-1-(2-fluorophenyl)hydrazono]ethyl}-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole with biological targets dopamine D2 receptor and enzymes monoamine oxidase A and B is discussed. Harmine alkaloid derivatives were studied for antidepressant and analgesic activity. It was found that 8-{(Z)-1-[(Z)-(2-fluorophenyl) hydrazono]ethyl}-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole at a dose of 10 mg/kg exhibited antidepressant effect in the Porsolt behavioral despair test. (Z)-8-(1-Hydrazonoethyl)-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole has a pronounced analgesic activity. Modeling of biological activity using PASS software predicted HIV attachment inhibiting, antimycobacterial, antituberculosic, histamine release inhibiting, cytochrome P450 stimulating, and various antineoplastic activities for synthesized harmine derivatives with high probability.

alkaloids , analgesic activity , antidepressant effect , harmine , molecular docking

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JSC International Scientific and Production Holding “Phytochemistry”, 4 Gazalieva St., Karaganda, 100009, Kazakhstan
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russian Federation
Department of Pharmaceutical and Toxicological Chemistry, Pharmacognosy, and Botany, School of Pharmacy, Asfendiyarov Kazakh National Medical University, 94 Tole Bi St, Almaty, Kazakhstan

JSC International Scientific and Production Holding “Phytochemistry”
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
Department of Pharmaceutical and Toxicological Chemistry

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