CAS: 117048-59-6; (Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Phenol

该化合物是一种自然产生的化合物,产自Combretum咖啡林树的树皮,以其强大的抗癌特性而著称;它属于二苯类,并因其抑制管状聚合的能力而得到承认,从而干扰了细胞分裂所必需的微囊的形成;这一机制使它成为癌症治疗的有希望的候选体,特别是针对固体肿瘤的治疗;该化合物的分子重量相对较低,其特征是特定的结构特征,包括跨石质结构;Combretastatin A4在临床前研究中显示,它对各种癌症细胞线具有严重的细胞毒性;此外,还调查了它有可能提高其他乳腺剂的功效,并导致肿瘤血管血管崩溃,从而减少肿瘤血液供应;然而,它的临床应用受到诸如溶性性和稳定性等因素的限制,促使对其衍生物和配方进行持续研究,以改善治疗结果.

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合成工艺路线路线简述

    (E)-3-(3-Acetoxy-4-Methoxyphenyl)-2-(3,4,5-Trimethoxyphenyl)Acrylic Acid置于喹啉,Copper Chromite 吡啶,乙酸酐,盐酸,Sodium Hydroxide,水体系中,化学反应 2.25H,以59%的收率获得(Z)-3,4,5,4',-四甲氧基-3'-羟基二苯乙烯
    参考文献:Wo2007/59118
    标题:Wo2007/59118

    海关参考信息

    专利信息


    专利号:US-2025101045-A1
    优先权日:2022-01-18
    标题:Synthesis of boron-containing amidoxime reagents and their application to synthesize functionalized oxadiazole and quinazolinone derivatives
    发明人:DAS BHASKAR
    权利人:LONG ISLAND UNIV
    摘要:The present disclosure is concerned with borylated amidoximes useful in the synthesis of biologically relevant drug-like molecules, including functionalized oxadizole and quinazolinone derivatives. Also disclosed are methods of making borylated amidoximes, methods of making functionalized oxadiazole and quinazolinone compounds using the amidoximes, and functionalized oxadiazole and quinazolinone compounds prepared from borylated amidoximes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

    专利号:US-12391691-B2
    优先权日:2018-11-16
    标题:Synthesis of key intermediate of KRAS G12C inhibitor compound
    发明人:PARSONS ANDREW THOMAS; COCHRAN BRIAN MCNEIL; POWAZINIK IV WILLIAM; CAPORINI MARC ANTHONY
    权利人:AMGEN INC
    摘要:The present invention relates to an improved, efficient, scalable process to prepare intermediate compounds, such as compound 5M, having the structure n nuseful for the synthesis of compounds that target KRAS G12C mutations, such as

    专利号:US-2025206736-A1
    优先权日:2019-11-14
    标题 :Synthesis of kras g12c inhibitor compound
    发明人:CORBETT MICHAEL THOMAS; CAILLE SEBASTIEN
    权利人:AMGEN INC
    摘要:The present disclosure relates to an improved, efficient, scalable process to prepare intermediate compounds, such as 2-isopropyl-4-methylpyridin-3-amine, useful for the synthesis of compounds, such as Compound 9, for the treatment of KRAS G12C mutated cancers.

    专利号:US-7105695-B2
    优先权日:2001-12-21
    标题 :Synthesis of combretastatin A-2 prodrugs
    发明人:PETTIT GEORGE R; MOSER BRYAN R
    权利人:UNIV ARIZONA STATE
    摘要:The original synthesis of combretastatin A-2 (1a) was modified to provide an efficient scale-up procedure for obtaining this antineoplastic stilbene. Subsequent conversion to a useful prodrug was accomplished by phosphorylation employing in situ formation of dibenzylchlorophosphite followed by cleavage of the benzyl ester protective groups with bromotrimethylsilane to afford phosphoric acid intermediate 11. The latter was immediately treated with sodium methoxide to complete a practical route to the disodium phosphate prodrug (2a). The phosphoric acid precursor (11) of phosphate 2a was employed in a parallel series of reactions to produce a selection of metal and ammonium cation prodrug candidates. Each of the phosphate salts (2a–q) was evaluated with respect to relative solubility behavior, cancer cell growth inhibition, and antimicrobial activity.

    专利号:US-2005130221-A1
    优先权日:2001-02-01
    标 题:Synthesis for the preparation of compounds for screening as potential tubulin binding agents
    发明人:FLYNN BERNARD L; HAMEL ERNEST
    权利人:US GOV HEALTH & HUMAN SERV
    摘要:The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

    专利号:US-2009099218-A1
    优先权日:2007-09-17
    标题 :Synthesis of novel tubulin polymerization inhibitors: benzoylphenylurea (bpu) sulfur analogs
    发明人:KHAN SAEED R; HALLUR GURULINGAPPA; HIDALGO MANUEL; JIMENO ANTONIO
    权利人:KHAN SAEED R; HALLUR GURULINGAPPA; HIDALGO MANUEL; JIMENO ANTONIO
    摘要:This invention provides a series of BPU analogues; their synthesis and evaluated biological activity. BPU sulfur analogues were found to possess up to 20 fold increased potency, when compared to compound 1, in various cancerous cell lines.
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    主要参考文献

    1. Sun, L., Vasilevich, N.I., Fuselier, J.A., et al. Abilities of 3,4-diarylfuran-2-one analogs of combretastatin A-4 to inhibit both proliferation of tumor cell lines and growth of relevant tumors in nude mice. Anticancer Research 24, 179-186 (2004). 2. Dey, P. Chromatin remodeling, cancer and chemotherapy. Current Medicinal Chemistry 13, 2909-2919 (2006).

    合成参考文献


    参考文献:10.1055/s-0029-1217010
    摘要:Narender T, Papi Reddy K, Madhur G. Synthesis of (E)-Stilbenes and (E,E)-1,4-Diphenylbuta-1,3-diene Promoted by Boron Trifluoride-Diethyl Ether Complex. Synthesis. 2009 Sep 23;2009(22):3791–6. doi: 10.1055/s-0029-1217010.
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