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Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives. / Adekenov, Sergazy M.; Zhanimkhanova, Pernesh Zh; Nurmaganbetov, Zhangeldy S. et al.

In: Chemistry of Heterocyclic Compounds, Vol. 55, No. 2, 15.02.2019, p. 135-141.

Research output: Contribution to journal › Article › peer-review

Harvard

Adekenov, SM, Zhanimkhanova, PZ, Nurmaganbetov, ZS, Amanzhan, A, Chernov, SV, Turmukhambetov, AZ, Bagryanskaya, IY, Gatilov, YV & Shults, EE 2019, 'Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives', Chemistry of Heterocyclic Compounds, vol. 55, no. 2, pp. 135-141. https://doi.org/10.1007/s10593-019-02429-1

APA

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. (2019). Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives. Chemistry of Heterocyclic Compounds, 55(2), 135-141. https://doi.org/10.1007/s10593-019-02429-1

Vancouver

Adekenov SM, Zhanimkhanova PZ, Nurmaganbetov ZS, Amanzhan A, Chernov SV, Turmukhambetov AZ et al. Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives. Chemistry of Heterocyclic Compounds. 2019 Feb 15;55(2):135-141. doi: 10.1007/s10593-019-02429-1

Author

Adekenov, Sergazy M. ; Zhanimkhanova, Pernesh Zh ; Nurmaganbetov, Zhangeldy S. et al. / Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives. In: Chemistry of Heterocyclic Compounds. 2019 ; Vol. 55, No. 2. pp. 135-141.

BibTeX

@article{cd95eddb0e95498bbed9e525226a656e,
title = "Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives",
abstract = "Hybrid molecules containing β-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.",
keywords = "8-acetylharmine, 8-formylharmine, chalcones, pyrazolines, X-ray structural analysis, β-carbolines, MONOAMINE-OXIDASE, APOPTOSIS, BETA-CARBOLINES, ANTI-ALZHEIMER, IN-VITRO, INHIBITION, ANTICANCER, -carbolines, BIOLOGICAL EVALUATION, NF-KAPPA-B, CYTOTOXICITY",
author = "Adekenov, {Sergazy M.} and Zhanimkhanova, {Pernesh Zh} and Nurmaganbetov, {Zhangeldy S.} and Asel Amanzhan and Chernov, {Sergey V.} and Turmukhambetov, {Aibek Zh} and Bagryanskaya, {Irina Yu} and Gatilov, {Yurii V.} and Shults, {Elvira E.}",
year = "2019",
month = feb,
day = "15",
doi = "10.1007/s10593-019-02429-1",
language = "English",
volume = "55",
pages = "135--141",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer New York",
number = "2",

}

RIS

TY - JOUR

T1 - Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives

AU - Adekenov, Sergazy M.

AU - Zhanimkhanova, Pernesh Zh

AU - Nurmaganbetov, Zhangeldy S.

AU - Amanzhan, Asel

AU - Chernov, Sergey V.

AU - Turmukhambetov, Aibek Zh

AU - Bagryanskaya, Irina Yu

AU - Gatilov, Yurii V.

AU - Shults, Elvira E.

PY - 2019/2/15

Y1 - 2019/2/15

N2 - Hybrid molecules containing β-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.

AB - Hybrid molecules containing β-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.

KW - 8-acetylharmine

KW - 8-formylharmine

KW - chalcones

KW - pyrazolines

KW - X-ray structural analysis

KW - β-carbolines

KW - MONOAMINE-OXIDASE

KW - APOPTOSIS

KW - BETA-CARBOLINES

KW - ANTI-ALZHEIMER

KW - IN-VITRO

KW - INHIBITION

KW - ANTICANCER

KW - -carbolines

KW - BIOLOGICAL EVALUATION

KW - NF-KAPPA-B

KW - CYTOTOXICITY

UR - http://www.scopus.com/inward/record.url?scp=85063998480&partnerID=8YFLogxK

U2 - 10.1007/s10593-019-02429-1

DO - 10.1007/s10593-019-02429-1

M3 - Article

AN - SCOPUS:85063998480

VL - 55

SP - 135

EP - 141

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 2

ER -

ID: 19355808