Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives

Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2019, Volume: 55, Number: 2, Pages: 135-141 Pages count : 7 DOI: 10.1007/s10593-019-02429-1

Tags

8-acetylharmine; -carbolines; chalcones; 8-formylharmine; pyrazolines; X-ray structural analysis

Authors

Adekenov Sergazy M. ¹ , Zhanimkhanova Pernesh Zh. ¹ , Nurmaganbetov Zhangeldy S. ¹ , Amanzhan Asel ¹ , Chernov Sergey V. ² , Turmukhambetov Aibek Zh. ¹ , Bagryanskaya Irina Yu. ^2,3 , Gatilov Yurii V. ^2,3 , Shults Elvira E. ^2,3

Affiliations

1	(Данные Web of science) JSC Int Res & Prod Holding Phytochem, 4 M Gazaliev St, Karaganda 100009, Kazakhstan
2	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 8 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, 1 Pirogova St, Novosibirsk 630090, Russia

Hybrid molecules containing -carboline and 1-acetylpyrazoline moieties were obtained on the basis of the alkaloid harmine. The synthetic procedure included acetylation of harmine with acetyl chloride in the presence of tin(IV) chloride, Claisen-Schmidt condensation with benzaldehydes under basic conditions, and cyclization of the obtained chalcones by the action of hydrazine hydrate and acetic acid. In addition, a method was proposed for the preparation of 8-formylharmine by treating harmine with dichloromethoxymethane in the presence of tin(IV) chloride. The structures of the synthesized compounds were confirmed by NMR spectra, mass spectra, and X-ray structural analysis.

Adekenov S.M. , Zhanimkhanova P.Z. , Nurmaganbetov Z.S. , Amanzhan A. , Chernov S.V. , Turmukhambetov A.Z. , Bagryanskaya I.Y. , Gatilov Y.V. , Shults E.E.
Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives
Chemistry of Heterocyclic Compounds. 2019. V.55. N2. P.135-141. DOI: 10.1007/s10593-019-02429-1 WOS Scopus РИНЦ

Published print:	Feb 1, 2019
Published online:	Mar 21, 2019

Web of science	WOS:000463779400004
Scopus	2-s2.0-85063998480
Elibrary	38672432
OpenAlex	W2924613631