CAS: 4429-63-4; Methyl (3Ar,3A1S,10Br)-3A-Ethyl-3A,3A1,4,6,11,12-Hexahydro-1H-Indolizino[8,1-Cd]Carbazole-5-Carboxylate

该化合物是一种自然产生的藻类,主要来自属于亚伯纳宫家族的Tabernaemontana divalicataa植物,其特点是复杂的蛋白结构,有助于其生物活动; 塔伯森尼表现出一系列药理特性,包括抗炎,止痛和潜在的抗癌影响,使其成为医学化学的一个主题; 该化合物通常以白到白的晶状固体的形式出现,在有机溶剂中溶解; 其分子公式反映了碳,氢,氮和氧原子的具体安排,这对于其生物相互作用至关重要; 对塔伯森的研究突出其作为药物发展主要化合物的潜力,特别是在治疗各种疾病方面; 但是,必须进行进一步研究,以充分了解其行动和治疗潜力的机制.与许多阿勒尼相比,塔伯宁的影响可能因剂量和研究的生物系统而不同.

结构式图片

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CAS号55856-70-7 19-Iodo-tabersonine | CAS号17640-15-2 氰基甲酸甲酯 | CAS号32975-46-5 (3aR,10bR)-3aα-... | CAS号41787-54-6 16-epi-19-S-vin... | CAS号80642-07-5 5-(chloromethyl... | CAS号66859-22-1 1,2,3,4,5,6-Hex... | CAS号536-78-7 3-乙基吡啶 | CAS号23995-13-3 1-methyl-carbaz... | CAS号120202-64-4 Ervayunine

合成工艺路线路线简述

    2-甲基吲哚-3-甲醛置于咪唑,盐酸,Titanium(Iv) Tetraethanolate,Potassium Tert-Butylate,Sodium Hydride,亚甲基三苯基膦烷,Lithium Hexamethyldisilazane,Lithium Diisopropyl Amide体系中,用 四氢呋喃,水,N,N-二甲基甲酰胺 作为反应溶剂,化学反应 24.0H,反应生成 它勃宁
    参考文献:芳烃融合的米歇尔.迈克尔/曼尼希反应的发展和范围:在孢霉属生物碱(-)-曲霉精,(-)-他布森碱和(-)-长春花碱的总合成中的应用
    标题:芳烃融合的米歇尔.迈克尔/曼尼希反应的发展和范围:在孢霉属生物碱(-)-曲霉精,(-)-他布森碱和(-)-长春花碱的总合成中的应用
    摘要:描述了芳烃融合的多米诺骨牌迈克尔/曼尼希路线的开发和应用,将其与曲霉生物碱的四氢咔唑(abe)核心结合使用.就亲核组分(即,N-亚磺酰基金属亚胺)和亲电组分(即,迈克尔受体)研究了该新型转化的范围.还讨论了该方法在10-11个步骤中分别分别成功合成简明的吲哚生物碱(-)-Aspidospermidine,(-)-Tabersonine和(-)-Vincadifformine的简明总合成方法.
    DOI:10.1021/acs.Joc.6B02551

    海关参考信息

    专利信息


    专利号:US-2025092433-A1
    优先权日:2023-09-20
    标 题:Polypeptides for use in the synthesis of kratom alkaloids
    发明人:CASARETTO JOSE; AKTAR TARIQ A; ROTHSTEIN STEVEN; SOUBEYRAND ERIC
    权利人:MITRADYNE CORP
    摘要:Described herein are polypeptides encoding enzymes for the synthesis of monoterpene indole alkaloids. For example, the polypeptide comprises or consists of the sequence of SEQ ID NO: 1-68, or a variant thereof having at least 80% sequence identity to SEQ ID NO: 1-68, or a fragment of the polypeptide, or the variant thereof.

    专利号:US-4400249-A
    优先权日:1980-09-30
    标 题:Partial synthesis process for preparing (+) -vincamine and related indolic alkaloids
    发明人:BENARDELLI GIOVANNI
    权利人:LINNEA SA
    摘要:A process of partial synthesis of vincamine and related indolic alkaloids for use as the active principal ingredient in drugs for treatment of diseases of the circulatory system and the central nervous system. The process includes the technique of activating oxygen in the elementary state in situ into an excited singlet state for chemical reaction by subjecting a reaction mixture to gaseous oxygen blowing under substantially ambient temperature and pressure conditions while effecting irradiation of the mixture by a light source. Operating conditions of the partial synthesis process are simplified, treatment times are reduced, and conversion yields are high.

    专利号:US-2025304985-A1
    优先权日:2022-04-08
    标题 :Genetically Engineered Plants for Increased Production of Vindoline
    发明人:LEE-PARSONS CAROLYN; COLE LAUREN F
    权利人:UNIV NORTHEASTERN
    摘要:Two novel transcription factors, CrDELLA1 and CrDELLA2, are described in Catharanthus roseus plants. The DELLA transcription factors have a regulatory role in the synthesis of vinblastine and vincristine, two important anti-cancer compounds that have proved difficult to obtain in sufficient quantities. The present technology provides genetically modified C. roseus plants having enhanced DELLA activity, which leads to activation of multiple enzymes in the biosynthetic pathway leading to vinblastine and vincristine. The genetic modifications can be used together with activation of plant defense mechanisms and responses to light in order to boost vinblastine and vincristine synthesis.

    专利号:US-4316029-A
    优先权日:1979-06-22
    标 题:Synthesis of vincaminic acid derivatives
    发明人:ROSSEY GUY
    权利人:SYNTHELABO
    摘要:Vincaminic acid derivatives of formula (A) ##STR1## useful in treating cerebral insufficiency, are prepared by reacting 1-ethyl-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizine with the 2,4-DNP hydrazone of ethyl or methyl bromopyruvate followed by (i) reduction of the Câ•?N bond and (ii) simultaneous cyclization with removal of the ketone-protecting group in either order.

    专利号:US-11072613-B2
    优先权日:2016-03-02
    标 题:Compositions and methods for making terpenoid indole alkaloids
    发明人:DE LUCA VINCENZO; QU YANG
    权利人:WILLOW BIOSCIENCES INC
    摘要:Methods that may be used for the manufacture of a class of chemical compounds known as terpenoid indole alkaloids, including tabersonine and catharanthine are provided. Compositions useful for the synthesis of terpenoid indole alkaloids, including tabersonine and catharanthine are also provided. The provided compounds are useful in the manufacture of chemotherapeutic agents.

    专利号:EP-4538367-A2
    优先权日:2023-09-20
    标 题:Polypeptides for use in the synthesis of kratom alkaloids
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    CAS号:4429-63-4
    中文名:水甘草碱
    英文名:TABERSONINE
    纯度:99% HPLC1G/5G/1KG
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    主要参考文献


    1: Kamileen MO, Nakamura Y, Luck K, Heinicke S, Hong B, Colinas M, Lichman BR, O'Connor SE. Streamlined screening platforms lead to the discovery of pachysiphine synthase from Tabernanthe iboga. New Phytol. 2024 Sep 16. doi: 10.1111/nph.20133. Epub ahead of print. 62(1):394-403. doi: 10.1080/13880209.2024.2351934. Epub 2024 May 13.
    4: Li X, Li X, Chen L, Deng Y, Zheng Z, Ming Y. Tabersonine Induces the Apoptosis of Human Hepatocellular Carcinoma In vitro and In vivo. Anticancer Agents Med Chem. 2024;24(10):764-772. doi: 10.2174/0118715206286612240303172230.
    5: Chen X, Yan Y, Liu Y, Yi Q, Xu Z. Tabersonine Enhances Olaparib Sensitivity through FHL1-Mediated Epithelial-Mesenchymal Transition in an Ovarian Tumor. J Nat Prod. 2024 Apr 26;87(4):837-848. doi: 10.1021/acs.jnatprod.3c01056. Epub 2024 Feb 28. 121(7):e2318586121. doi: 10.1073/pnas.2318586121. Epub 2024 Feb 6.

    合成参考文献


    参考文献:10.1007/s004380050006
    摘要:Ouwerkerk PBF, Memelink J. A G-box element from the Catharanthus roseus strictosidine synthase (Str) gene promoter confers seed-specific expression in transgenic tobacco plants. Molecular Genetics and Genomics. 1999 Jun;261(4-5):635–43. doi: 10.1007/s004380050006.
    参考文献:10.1021/ja017863s
    摘要:Kozmin SA, Iwama T, Huang Y, Rawal VH. An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine. J Am Chem Soc. 2002 May 01;124(17):4628–41. doi: 10.1021/ja017863s.
    参考文献:10.1126/science.aat4100
    摘要:Caputi L, Franke J, Farrow SC, Chung K, Payne RME, Nguyen TD, Dang TT, Soares Teto Carqueijeiro I, Koudounas K, Dugé de Bernonville T, Ameyaw B, Jones DM, Vieira IJC, Courdavault V, O'Connor SE. Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle. Science. 2018 Jun 15;360(6394):1235–9. doi: 10.1126/science.aat4100.
    参考文献:10.1007/s12298-020-00842-x
    摘要:Verma P, Singh N, Khan SA, Mathur AK, Sharma A, Jamal F. TIAs pathway genes and associated miRNA identification in Vinca minor: supporting aspidosperma and eburnamine alkaloids linkage via transcriptomic analysis. Physiology and Molecular Biology of Plants. 2020 Jul 08;26(8):1695–711. doi: 10.1007/s12298-020-00842-x.
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