CAS: 26833-85-2; (R)-1-((11Bs,12S,14Ar)-13-Methoxy-2,3,5,6,11B,12-Hexahydro-1H-[1,3]Dioxolo[4',5':4,5]Benzo[1,2-D]Cyclopenta[b]Pyrrolo[1,2-A]Azepin-12-yl) 4-Methyl 2-Hydroxy-2-(3-Hydroxy-3-Methylbutyl)Succinate

该化合物是一种天然的藻类,产自植物物种Cephalotaxus harringtonia, 通称为日本羽羽毛.它被归类为蛋白合成的强力抑制剂,具体针对乳液性脊髓炎.哈林顿因蛋白质表现出抗沙素特性,并研究其在治疗各种癌症,特别是急性流星素白血病方面的潜在用途.该化合物因其在癌症细胞中诱发流行性疾病的能力而闻名,因此成为癌症研究的一个主题.就其化学结构而言,哈林顿因子具有复杂的多环形框架,有助于其生物活动.它通常通过静脉注射进行,原因是其口服生物利用率低.和许多alkaloids一样,哈林顿因子可能会产生副作用,而且其使用往往伴随着临床环境的仔细监测.

结构式图片

欧盟法规

C&L通报

上下游产品

R)-2-methoxy-(3arC4,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester(Ξ)-2-benzyloxy-2-(3-hydroxy-3-methyl-butyl)-succinic acid 1-((3aR)-2-methoxy-(3arC4,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester 4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carbonyl chloride R)-2-methoxy-(3arC4,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl ester(Ξ)-4-benzyloxy-7,7-dimethyl-2-oxo-oxepane-4-carboxylic acid (3aR)-2-methoxy-(3arC4,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl ester cephalotaxine

合成工艺路线路线简述

    📜1-O-[(2S,3S,6R)-4-Methoxy-16,18-Dioxa-10-Azapentacyclo[11.7.0.02,6.06,10.015,19]Icosa-1(20),4,13,15(19)-Tetraen-3-Yl] 4-O-Methyl (2R)-2-[3-[tert-Butyl(Dimethyl)Silyl]Oxy-3-Methylbutyl]-2-Hydroxybutanedioate置于triethylamine Tris(Hydrogen Fluoride),三乙胺体系中,用 乙腈 用作溶剂,化学反应 72.0H,以92%的收率获得三尖杉酯碱
    参考文献:非对称mukaiyama Aldol反应的非对映选择性合成头孢酯.
    标题:非对称mukaiyama Aldol反应的非对映选择性合成头孢酯.
    摘要:我们报告了协议的高效立体选择性安装头孢酯侧链的手性含氧四取代叔碳立体中心通过α-酮酸酯(2)和(z)-α-氯之间的高度非对映选择性的mukaiyama羟醛反应乙烯酮甲硅烷基缩醛.该方案允许合成头孢菌素酯,包括具有高非对映选择性(dr高达97:3)的高至极佳产率(高达94%)的六种天然产物,并且可以以多克规模进行.
    Doi:10.1021/acs.Orglett.7B00743

    海关参考信息

    专利信息


    专利号:WO-02055470-A1
    优先权日:2000-12-29
    标 题 :Method for the enantioselective preparation of adducts of $g(a)-substituted phenylethylamine-cycloalkanes and of 2-acetoxyacrylonitrile, intermediates in the enantioselective synthesis of the lateral chain of harringtonines
    发明人:DUMAS FRANCOISE; ROBIN JEAN-PIERRE; KELLER LAURENT; BATAILLE PATRICIA; D ANGELO JEAN
    权利人:ONCOPHARM; CENTRE NAT RECH SCIENT; DUMAS FRANCOISE; ROBIN JEAN-PIERRE; KELLER LAURENT; BATAILLE PATRICIA; D ANGELO JEAN
    摘要:The invention relates to a method for the enantioselective preparation of adducts of alpha -substituted phenylethylimino-cycloalkanes and of 2-acetoxyacrylonitrile with the formula (I), wherein the carbon atom in position 1' has the stereochemistry 1'S or 1'R; n = 0 to 3; Z is a protected alcohol radical having the formula OGP<1>; GP<1> is a protective group such as a carbon-containing ether, a silylated ether or an ester; GP<2> is a protective group of enols such as a silylated ether; and involving a Michael reaction between the methyl cyanoacetate and a chiral imine.

    专利号:WO-2025032401-A1
    优先权日:2023-08-07
    标题:Method for identifying 3'p rna fragments as modulators of ribosomes and protein synthesis
    发明人:DEL PIANO ALESSIA; KECMAN TEA; CLAMER MASSIMILIANO
    权利人:IMMAGINA BIOTECHNOLOGY S R L
    摘要:A method for the identification of RNA fragments comprising a 3' phosphate or a 2'/3' cyclic phosphate as modulators of ribosomes and protein synthesis.

    专利号:US-12161658-B2
    优先权日:2017-11-10
    标 题 :Compositions and methods for the treatment of expanded repeat-associated disorders
    发明人:RICHTER JOEL D; GAO FEN-BIAO
    权利人:UNIV MASSACHUSETTS
    摘要:Translation modulating agents that modulate expression of one or more translation start sites for expanded repeat (e.g., DPR) protein synthesis are provided. Compositions and methods for treating translation start sites for expanded repeat (e.g., DPR) protein synthesis-associated disorders are also provided.

    专利号:US-2007166415-A1
    优先权日:2006-01-18
    标题:Safe medicine for treating and preventing cancer and method of use
    发明人:LIU YAGUANG
    权利人:LIU YAGUANG
    摘要:The present invention provides a new method for extracting Homoharringtonine (HHT) by culture cells or culture plant tissues. Also, disclosed are methods of obtaining HHT from semi-synthesis and biosynthesis. The present invention disclosed that HHT combined with some botanical drugs could induce cancer cells to resemble normal cells. To add some botanical drugs combined with HHT can significantly increase anticancer effects of HHT. These drugs include Matrine (MAT), Guanzhongsu (GU), Maidongsu (MU), and Indirubin (IND). The experimental data showed that above drugs have strong synergisms effects for treating leukemia and other cancer cells and more safe.

    专利号:US-10183955-B2
    优先权日:2015-07-21
    标题:Molecules for isolation of polyribosomes, ribosomes, uses and kits thereof
    发明人:CLAMER MASSIMILIANO; VIERO GABRIELLA; GUELLA GRAZIANO; QUATTRONE ALESSANDRO
    权利人:IMMAGINA BIOTECHNOLOGY S R L
    摘要:Molecules of general Formula (I): able to bind to native polyribosomes engaged in active protein synthesis. The disclosure relates also to the use of the molecules of general Formula (I) for isolating at least one active ribosome from a biological sample, and for ribosome profiling, as well as kits for isolating at least one active ribosome from a biological sample.

    专利号:US-12410437-B2
    优先权日:2016-07-12
    标 题:Incorporation of internal polya-encoded poly-lysine sequence tags and their variations for the tunable control of protein synthesis in bacterial and eukaryotic cells
    发明人:DJURANOVIC SERGEJ; GREEN RACHEL
    权利人:WASHINGTON UNIVERSITY ST LOUIS; UNIV JOHNS HOPKINS
    摘要:The present disclosure relates to modulation of protein expression.

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Kaur P, Thiruchelvan M, Lee RC, Chen H, Chen KC, Ng ML, Chu JJ. Inhibition of chikungunya virus replication by harringtonine, a novel antiviral that suppresses viral protein expression. Antimicrob Agents Chemother. 2013 Jan;57(1):155-67. doi: 10.1128/AAC.01467-12. Epub 2012 Oct 22.
    2: Moirangthem DS, Borah JC, Laishram S, Kalita MC, Talukdar NC. HPLC analysis of harringtonine and homoharringtonine in the needles of Cephalotaxus griffithii alkaloid fraction and cytotoxic activity on chronic myelogenous leukaemia K562 cell. Nat Prod Res. 2014;28(18):1503-6. doi: 10.1080/14786419.2014.913241. Epub 2014 Apr 30. doi: 10.1021/jo302203g. Epub 2012 Dec 18. Chinese. doi: 10.1038/nprot.2012.086.
    6: Cao W, Liu Y, Zhang R, Zhang B, Wang T, Zhu X, Mei L, Chen H, Zhang H, Ming P, Huang L. Homoharringtonine induces apoptosis and inhibits STAT3 via IL-6/JAK1/STAT3 signal pathway in Gefitinib-resistant lung cancer cells. Sci Rep. 2015 Jul 13;5:8477. doi: 10.1038/srep08477.

    合成参考文献


    参考文献:10.5281/zenodo.5794106
    摘要:The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
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