methyl 3-(4-carboxymethylphenyl)acrylate | 153464-15-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 3-(4-carboxymethylphenyl)acrylate
• 英文别名: 2-[4-(3-Methoxy-3-oxoprop-1-enyl)phenyl]acetic acid
• CAS: 153464-15-4
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: PRYGIHPZXVXTJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-carboxymethylphenyl)acrylate 在 盐酸羟胺 、 氨 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 N-cyclopropyl-3-(4-fluorophenyl)-2-{4-[(1E)-3-(hydroxyamino)-3-oxoprop-1-en-1-yl]phenyl}acrylamide
  参考文献：
  名称：

  Orally available stilbene derivatives as potent HDAC inhibitors with antiproliferative activities and antitumor effects in human tumor xenografts

  摘要：

  Herein we report the synthesis and activity of a novel class of HDAC inhibitors based on 2, 3-diphenyl acrylic acid derivatives. The compounds in this series have shown to be potent HDAC inhibitors possessing significant antiproliferative activity. Further compounds in this series were subjected to metabolic stability in human liver microsomes (HLM), mouse liver microsomes (MLM), and exhibits promising stability in both. These efforts culminated with the identification of a developmental candidate (5a), which displayed desirable PK/PD relationships, significant efficacy in the xenograft models and attractive ADME profiles. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.014
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 对溴苯乙酸 在 palladium diacetate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 生成 methyl 3-(4-carboxymethylphenyl)acrylate
  参考文献：
  名称：

  Orally available stilbene derivatives as potent HDAC inhibitors with antiproliferative activities and antitumor effects in human tumor xenografts

  摘要：

  Herein we report the synthesis and activity of a novel class of HDAC inhibitors based on 2, 3-diphenyl acrylic acid derivatives. The compounds in this series have shown to be potent HDAC inhibitors possessing significant antiproliferative activity. Further compounds in this series were subjected to metabolic stability in human liver microsomes (HLM), mouse liver microsomes (MLM), and exhibits promising stability in both. These efforts culminated with the identification of a developmental candidate (5a), which displayed desirable PK/PD relationships, significant efficacy in the xenograft models and attractive ADME profiles. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.014

文献信息

• Ti/Ni-Mediated Inter- and Intramolecular Conjugate Addition of Aryl and Alkenyl Halides and Triflates
  作者：Irene R. Márquez、Delia Miguel、Alba Millán、M. Luisa Marcos、Luis Álvarez de Cienfuegos、Araceli G. Campaña、Juan M. Cuerva

  DOI：10.1021/jo402626u

  日期：2014.2.21

  extent, chlorides and triflates to α,β-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five- and six-membered rings are obtained in good yields.

  在这项工作中，我们表明，镍催化剂和Cp 2 TiCl的独特组合可以在室温下直接共轭添加芳基和链烯基碘化物，溴化物，并在较小程度上将氯化物和三氟甲磺酸盐生成α，β-不饱和羰基。 ，而无需事先形成有机金属亲核试剂。该反应在分子间和分子内以良好的官能团相容性进行，这是开发自由保护基方法的关键。五元环和六元环的碳环和杂环以高收率获得。此外，从循环伏安法，UV-vis和HRTEM测量中获得了有关机理的一些见解。
• HDAC INHIBITORS
  申请人：Davidson Alan Hornsby

  公开号：US20100010010A1

  公开（公告）日：2010-01-14

  Compounds of formula (I) inhibit HDAC activity, wherein A, B and D independently represent ═C— or ═N—; W is a divalent radical —CH═CH— or CH 2 CH 2 —; R 1 is a carboxylic acid group (—COOH), or an ester group which is hydrolysable by one or more intracellular carboxyesterase enzymes to a carboxylic acid group; R 2 is the side chain of a natural or non-natural alpha amino acid; z is 0 or 1; and Y, L 1 , and X 1 are as defined in the claims.

  公式（I）的化合物抑制HDAC活性，其中A、B和D分别表示═C—或═N—；W是二价基团—CH═CH—或CH2CH2—；R1是羧酸基（—COOH），或者是可被一个或多个细胞内羧酸酯酶水解为羧酸基的酯基团；R2是天然或非天然α氨基酸的侧链；z为0或1；Y、L1和X1如权利要求中所定义。
• HDAC inhibitor
  申请人：Chroma Therapeutics Limited

  公开号：EP2295410A1

  公开（公告）日：2011-03-16

  Cyclopentyl (2S)-cyclohexyl[(6-[3-(hydroxyamino)-3-oxopropyl]pyridin-3 yl}methyl)amino]acetate inhibits HDAC activity.

  (2S)-环己基[(6-[3-（羟基氨基）-3-氧代丙基]吡啶-3 yl}甲基）氨基]乙酸环戊酯可抑制 HDAC 活性。
• Preparation and use of palladium catalysts for cross-coupling reactions
  申请人：——

  公开号：US20020173421A1

  公开（公告）日：2002-11-21

  The invention relates to a process for preparing meterable solutions or dispersions of palladium catalysts, to these solutions or dispersions of such catalysts, and to the use of such catalysts in cross-coupling reactions.

  本发明涉及一种制备可计量的钯催化剂溶液或分散体的工艺、这些催化剂溶液或分散体以及在交叉偶联反应中使用这些催化剂。
• US5489693A
  申请人：——

  公开号：US5489693A

  公开（公告）日：1996-02-06