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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

Abstract: 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.
Cite: 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 OpenAlex
Dates:
Published print: Feb 1, 2019
Published online: Mar 21, 2019
Identifiers:
Web of science: WOS:000463779400004
Scopus: 2-s2.0-85063998480
Elibrary: 38672432
OpenAlex: W2924613631
Citing:
DB Citing
Web of science 4
Scopus 3
Elibrary 5
OpenAlex 3
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