CAS: 88457-23-2; Melphalan Methyl Ester

该化合物是一种合成有机化合物,属于氨基酸衍生物类别,其特征为甲酯功能组,可提高其在有机溶剂中的溶性;该化合物含有苯麻黄碱基,这是一种必要的氨基酸,并经过二(2-氯乙基)氨基组的修改,表明可能发生反应和生物活动,特别是在药用化学方面;这一结构表明,该物质组可能表现出与抗癌活动有关的特点,因为具有类似功能的化合物往往因其与生物目标相互作用的能力而受到调查;二(2-氯乙基)组中的氯原子也可能影响其药理学和毒性特征;

结构式图片

物理性质

MSDS等安全信息

    上下游产品

    (S)-3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[3-(2,4-dimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-methyl-butyrylamino]-propionic acid methyl ester (S)-3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[3-(5-bromo-2,4-dimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-3-methyl-butyrylamino]-propionic acid methyl ester (S)-3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[3-methyl-3-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-butyrylamino]-propionic acid methyl ester methanol

    合成工艺路线路线简述

    • 合成目标产物 Melphalan Ep Impurity H 主要起始原料 Methanol And Melphalan
    • (文献来源)合成步骤主要原料 Methanol 和 Melphalan
    📜甲醇,美法仑置于氯化亚砜体系中,化学反应 12.0H,以93%的收率获得产物美法仑甲酯
    参考文献:具有选择性抗增殖活性的新型氮芥-依维二胺杂种的设计与合成
    标题:具有选择性抗增殖活性的新型氮芥-依维二胺杂种的设计与合成
    摘要:合成了一系列新颖的氮芥-依夫二胺杂种,并评估了它们的抗增殖特性.10A-D,11A-D和12A-D的抗增殖活性确定了针对四种不同类型的人类癌细胞系(pc-3,Hepg2,Thp-1和hl-60)和人类正常外周血单个核细胞(pbmc)的抗性.结果表明,所有目标杂合化合物均在一定程度上显示出对被测人肿瘤细胞系的抗增殖活性,而对人正常pbmc细胞则无抗增殖活性(> 200μm).肿瘤细胞与正常细胞之间的抗增殖选择性对于进一步开发抗肿瘤药物非常有用.在目标化合物中,12C对两种肿瘤细胞系(thp-1和hl-60)表现出最强的细胞毒性,Ic 50值分别为4.05μm和0.50μm,并被选择用于hl-60细胞的进一步机制研究.结果表明12C可以通过线粒体相关途径诱导hl-60细胞凋亡,并在低亚微摩尔浓度下阻滞在g 2期.
    DOI:10.1016/j.Bmcl.2017.10.014

    海关参考信息

    专利信息


    专利号:US-8921596-B2
    优先权日:2010-11-04
    标 题:Process for the preparation of melphalan hydrochloride
    发明人：GURJAR MUKUND KESHAV; TRIPATHY NARENDRA KUMAR; KOTHARKAR SANDEEP ANILRAO; PATIL PRADIP NANA; MEHTA SAMIT SATISH
    权利人:GURJAR MUKUND KESHAV; TRIPATHY NARENDRA KUMAR; KOTHARKAR SANDEEP ANILRAO; PATIL PRADIP NANA; MEHTA SAMIT SATISH; EMCURE PHARMACEUTICALS LTD
    摘要:The present invention provides a simple and efficient method for synthesis of 4-[bis(2-chloroethyl)-amino]-L-phenylalanine hydrochloride. The process involves the treatment of 4-[bis(2-chloroethyl)-amino]-L-phenylalanine free base with hydrochloric acid in water followed by isolation of 4-[bis(2-chloroethyl)-amino]-L-phenylalanine hydrochloride of desired purity.

    专利号:US-2005214310-A1
    优先权日:2004-01-23
    标 题 :Melphalan prodrugs
    发明人：TOKI BRIAN E; SENTER PETER D
    权利人:SEATTLE GENETICS INC
    摘要:Shown and described are the synthesis of more potent forms of C-Mel, a prodrug used in Antibody-Directed Enzyme Prodrug Therapy, that releases the clinically used anticancer alkylating agent melphalan extracellularly. Shown and described are the synthesis of a variety of melphalan analogues with the intention to promote facile intracellular drug access. Esters, amides, and peptides of melphalan are shown. Cephalosporin prodrugs of the most interesting melphalan derivatives were synthesized and evaluated for potency, toxicity, therapeutic window, plasma stability, and solubility.

    专利号:TR-2021005890-A2
    优先权日:2021-04-01
    标 题 :SYNTHESIS OF GLYCOLYSED MELPHLANE DERIVATIVES

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    主要参考文献


    1: Noesslinger T, Panny M, Simanek R, Moestl M, Boehm A, Menschel E, Koller E, Keil F. High dose Bendamustine-EAM followed by autologous stem cell rescue results in long term remission rates in lymphoma patients, without renal toxicty. Eur J Haematol. 2018 May 25. doi: 10.1111/ejh.13102. [Epub ahead of print] Czech. doi: 10.11406/rinketsu.59.395. Japanese. doi: 10.1186/s12883-018-1071-y.
    10: Fan FS, Yang CF. Complete response to orally administered melphalan in malignant pleural effusion from an occult female genital organ primary neoplasm with BRCA1/2 mutations: a case report. J Med Case Rep. 2018 May 6;12(1):122. doi: 10.1186/s13256-018-1674-3.
    11: Hishiki T, Matsumoto K, Ohira M, Kamijo T, Shichino H, Kuroda T, Yoneda A, Soejima T, Nakazawa A, Takimoto T, Yokota I, Teramukai S, Takahashi H, Fukushima T, Kaneko T, Hara J, Kaneko M, Ikeda H, Tajiri T, Nakagawara A; Japan Childhood Cancer Group Neuroblastoma Committee (JNBSG). Results of a phase II trial for high-risk neuroblastoma treatment protocol JN-H-07: a report from the Japan Childhood Cancer Group Neuroblastoma Committee (JNBSG). Int J Clin Oncol. 2018 Apr 26. doi: 10.1007/s10147-018-1281-8. [Epub ahead of print] pii: E1278. doi: 10.3390/ijms19051278. Review. doi: 10.1111/bjh.15249. Epub 2018 Apr 20. High-dose Carboplatin/Etoposide/Melphalan increases risk of thrombotic microangiopathy and organ injury after autologous stem cell transplantation in patients with neuroblastoma. Bone Marrow Transplant. 2018 Apr 19. doi: 10.1038/s41409-018-0159-8. [Epub ahead of print]

    合成参考文献

    合成方法参考DOI号:10.1021/ml500141f
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