α-methyl-trans-α,β-epoxy-β-phenylpropanoic acid | 25547-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: α-methyl-trans-α,β-epoxy-β-phenylpropanoic acid
• 英文别名: trans-2-methyl-3-phenyl-2-oxiranecarboxylic acid；(+/-)-2,3-epoxy-2-methyl-3-phenylpropionic acid；2-methyl-3-phenyloxirane-2-carboxylic acid；trans-α,β-epoxy-α-methylcinnamic acid；(2RS,3SR)-2,3-epoxy-2-methyl-3-phenyl-propionic acid；(2RS,3SR)-2,3-Epoxy-2-methyl-3-phenyl-propionsaeure；(2R,3S)-2-methyl-3-phenyloxirane-2-carboxylic acid
• CAS: 25547-51-7；82812-97-3；82812-98-4
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: UPEAOFCHTFWNFG-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-methyl-trans-α,β-epoxy-β-phenylpropanoic acid 在 copper(II) nitrate sodium tetrahydroborate 、 sodium azide 作用下， 以 水 为溶剂， 反应 4.5h， 生成 (+/-)-(2S,3S)-3-amino-2-hydroxy-2-methyl-3-phenylpropanoic acid
  参考文献：
  名称：

  First One-Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-Amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines

  摘要：

  alpha-Hydroxy-beta-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.

  DOI：

  10.1021/jo034752y
• 作为产物：
  描述：

  2-甲基-3-苯基丙烯酸 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二异丙酯 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 生成 α-methyl-trans-α,β-epoxy-β-phenylpropanoic acid
  参考文献：
  名称：

  一种具有抗肿瘤活性的Chrysamide B衍生物及其制备和应用

  摘要：

  本发明属于药物化学领域，具体涉及一种海洋天然产物Chrysamide B及其衍生物，包括其立体异构体或药学上可接受的盐、溶剂化物和前药，通式为式（一）、式（二）和式（三），及所述化合物的制备和用途。本发明所述化合物具有抗癌作用，如对消化系统癌症、白血病、肝脏肿瘤、非小细胞肺癌、宫颈癌、乳腺癌等具有良好的抑制活性，并且所述化合物具有诱导肿瘤细胞凋亡和激活凋亡蛋白表达、阻滞周期和抑制增殖等作用，是一类具有潜在的抗肿瘤药物。。

  公开号：

  CN111440155B

文献信息

• Design, synthesis and antitumor activity evaluation of Chrysamide B derivatives
  作者：Longqing Zhu、Junfang Li、Xiaohong Fan、Xiaoling Hu、Jinhong Chen、Yonghong Liu、Xiangyong Hao、Tao Shi、Zhen Wang、Quanyi Zhao

  DOI：10.1016/j.bioorg.2021.104828

  日期：2021.6

  Marine natural products derived from special or extreme environment provide an important source for the development of anti-tumor drugs due to their special skeletons and functional groups. In this study, based on our previous work on the total synthesis and structure revision of the novel marine natural product Chrysamide B, a group of its derivatives were designed, synthesized, and subsequently of

  来自特殊或极端环境的海洋天然产物由于其特殊的骨架和功能基团，为抗肿瘤药物的开发提供了重要来源。本研究在我们前期对新型海洋天然产物菊酰胺 B 的全合成和结构修正的基础上，设计、合成了一组其衍生物，随后对其抗癌活性、构效关系和首次探索了细胞机制。与菊酰胺 B 相比，观察到某些衍生物对五种人类癌细胞系（SGC-7901、MGC-803、HepG2、HCT-116、MCF-7）具有更好的抗癌性能，尤其是化合物b-9对 MGC-带有 IC 50 的803 和 SGC-7901 电池值分别为 7.88 ± 0.81 和 10.08 ±1.08 μM。随后，细胞机制研究表明，b-9处理可抑制胃癌MGC-803和SGC-7901细胞的细胞增殖，降低细胞的迁移和侵袭能力，诱导线粒体依赖性凋亡。此外，化合物b-9诱导的线粒体依赖性细胞凋亡与JAK2/STAT3/Bcl-2信号通路有关。总而言之，我们的结果为从
• Antispasmodics. XVII. β-Diethylaminoethyl Esters of Substituted Acetic and Glycidic Acids
  作者：F. F. Blicke、J. A. Faust、H. Raffelson

  DOI：10.1021/ja01641a014

  日期：1954.6
• Bromolysis and Iodolysis of α,β-Epoxycarboxylic Acids in Water Catalyzed by Indium Halides
  作者：David Amantini、Francesco Fringuelli、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/jo0156215

  日期：2001.6.1

  The ring opening of alpha,beta -epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereoselective fashion. The iodolysis of trans-beta -monoalkylated epoxycarboxylic acids at pH 4.0 was completely ol-regioselective and anti diastereoselective. The InCl3-catalyzed iodolysis of a variety of alpha,beta -epoxycarboxylic acids at pH 1.5 gave the corresponding anti beta -iodohydrins in 88-95% yields. The one-pot synthesis of the alpha- and beta -hydroxyhexanoic acids, starting from the corresponding alpha,beta -epoxycarboxylic acid 1a by iodolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaBH4-InCl3 in water, has been performed.
• Bokanov, A. I.; Persianova, I. P.; Shvedov, V. I., Journal of Organic Chemistry USSR (English Translation), 1982, p. 971 - 972
  作者：Bokanov, A. I.、Persianova, I. P.、Shvedov, V. I.

  DOI：——

  日期：——
• AlCl 3 as an efficient Lewis acid catalyst in water
  作者：Francesco Fringuelli、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1016/s0040-4039(00)02164-x

  日期：2001.2

  For the first time AlCl3 has been conveniently employed as a Lewis acid in water and efficiently catalysed regio- and stereoselective azidolysis of alpha,beta -epoxycarboxylic acids in water. (C) 2001 Elsevier Science Ltd. All rights reserved.