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

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

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

机译：Carboline生物碱的合成修饰问题：8个取代衍生物的合成

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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.

机译：基于生物碱的气动获得含含碱和1-乙酰吡唑啉部分的杂化分子。合成程序包括在锡（IV）氯化锡的存在下用乙酰氯，Claisen-Schmidt缩合在基本条件下，通过肼水合物和乙酸的作用来环化所得硫酸的环化。此外，提出了一种通过在锡（IV）氯化物存在下用二氯甲氧基甲烷治疗问题来制备8-甲酰甲骨。通过NMR光谱，质谱和X射线结构分析证实了合成化合物的结构。

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来源
《Chemistry of heterocyclic compounds》 |2019年第2期|共7页
作者
Adekenov Sergazy M.; Zhanimkhanova Pernesh Zh.; Nurmaganbetov Zhangeldy S.; Amanzhan Asel; Chernov Sergey V.; Turmukhambetov Aibek Zh.; Bagryanskaya Irina Yu.; Gatilov Yurii V.; Shults Elvira E.;
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作者单位

JSC Int Res &

Prod Holding Phytochem 4 M Gazaliev St Karaganda 100009 Kazakhstan;

JSC Int Res &

Prod Holding Phytochem 4 M Gazaliev St Karaganda 100009 Kazakhstan;

JSC Int Res &

Prod Holding Phytochem 4 M Gazaliev St Karaganda 100009 Kazakhstan;

JSC Int Res &

Prod Holding Phytochem 4 M Gazaliev St Karaganda 100009 Kazakhstan;

Russian Acad Sci Siberian Branch NN Vorozhtsov Novosibirsk Inst Organ Chem 8 Akad Lavrentieva Ave Novosibirsk 630090 Russia;

JSC Int Res &

Prod Holding Phytochem 4 M Gazaliev St Karaganda 100009 Kazakhstan;

Russian Acad Sci Siberian Branch NN Vorozhtsov Novosibirsk Inst Organ Chem 8 Akad Lavrentieva Ave Novosibirsk 630090 Russia;

Russian Acad Sci Siberian Branch NN Vorozhtsov Novosibirsk Inst Organ Chem 8 Akad Lavrentieva Ave Novosibirsk 630090 Russia;

Russian Acad Sci Siberian Branch NN Vorozhtsov Novosibirsk Inst Organ Chem 8 Akad Lavrentieva Ave Novosibirsk 630090 Russia;

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原文格式 PDF
正文语种 eng
中图分类杂环化合物;
关键词
8-acetylharmine; -carbolines; chalcones; 8-formylharmine; pyrazolines; X-ray structural analysis;

机译：8-乙酰化;-Carbolines;chalcones;8-甲甲藓;吡唑啉;X射线结构分析;

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专利

1. Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives [J] . Adekenov Sergazy M., Zhanimkhanova Pernesh Zh., Nurmaganbetov Zhangeldy S., Chemistry of heterocyclic compounds . 2019,第2期

机译：Carboline生物碱的合成修饰问题：8个取代衍生物的合成
2. Quantitative structure-activity relationship of antitumor and neurotoxic β-carbolines alkaloids: Nine harmine derivatives [J] . Lamchouri F., Toufik H., Elmalki Z., Research on Chemical Intermediates . 2013,第5期

机译：抗肿瘤药和神经毒性β-咔啉生物碱的定量构效关系：九种harmine衍生物
3. Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by β-carboline alkaloids, harmine derivatives [J] . Zhao T., He Y.-Q., Wang J., Phytotherapy research: PTR . 2011,第11期

机译：β-咔啉生物碱，甜菜碱衍生物对人细胞色素P450酶3A4和2D6的抑制作用
4. Variety of natural products derived fromtryptophan and stereoselective synthesis oftetrahydro-beta-carboline derivatives ofpharmacological importance [C] . Piotr Roszkowski, Stefan Czarnocki, Jan K. Mauri International Study Group for Tryptophan Research . 2007

机译：各种天然产物源自源性产物和立体选择合成的四滴β-咔啉衍生物的形态重要性
5. Part One. Synthesis of optically active tryptophan derivatives with potential activity as indoleamine 2,3-dioxygenase inhibitors: An approach via asymmetric catalytic hydrogenation. Part Two. Design, synthesis and pharmacology of selective ligands for alpha1-containing GABA(A)/benzodiazepine receptor subtypes: SAR studies of beta-carbolines at positions -3 and -6 and their corresponding bivalent ligands. Part Three. First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A. [D] . Yin, Wenyuan. 2007

机译：第一部分。具有吲哚胺2,3-二加氧酶抑制剂潜在活性的旋光色氨酸衍生物的合成：一种通过不对称催化氢化的方法。第二部分。含α1的GABA（A）/苯并二氮杂receptor受体亚型的选择性配体的设计，合成和药理作用：位于-3和-6位的β-咔啉及其相应的二价配体的SAR研究。第三部分。重要生物遗传中间体，（+）-聚神经氨酸和（+）-聚神经氨酸醛，以及16-表-维西辛和Macusine A的首次对映体全合成。
6. Synthesis and Fungicidal Activity of β-Carboline Alkaloids and Their Derivatives [O] . Zhibin Li, Shaohua Chen, Shaowen Zhu, 2015

机译：β-咔啉生物碱及其衍生物的合成及杀真菌活性
7. Synthetic Derivatives of Natural Alkaloid Harmine [O] . N.M. Ismagulova, Zh.S. Nurmaganbetov, A.Zh. Turmukhambetov, 2016

机译：天然生物碱的合成衍生物

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

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