3-(4-chlorophenyl)-2-oxopropionic acid | 127273-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorophenyl)-2-oxopropionic acid
• 英文别名: 3-(4-chlorophenyl)-2-oxopropanoic acid；(Z)-3-(4-chlorophenyl)-2-hydroxyacrylic acid；2-hydroxy-3-(4-chlorophenyl)acrylic acid；3-(4-Chlorophenyl)-2-hydroxy-acrylic acid；(Z)-3-(4-chlorophenyl)-2-hydroxyprop-2-enoic acid
• CAS: 127273-12-5
• 化学式: C₉H₇ClO₃
• 分子量: 198.606
• InChiKey: LJIZTSRZWZUBJE-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-2-oxopropionic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 (Z)-3-(4-chlorophenyl)-2-methoxy-N-phenylacrylamide
  参考文献：
  名称：

  Synthesis of novel cinnamanilides as potential immunosuppressive agents

  摘要：

  A series of new cinnamanilides (6-40) were synthesized and their immunosuppressive activity and cytotoxicity were evaluated. Most of the cinnamanilides showed good immunosuppressive activity. Among the synthesized compounds, (Z)-N-(4-bromophenyl)-2-methoxy-3-(4-methoxyphenyl)acrylamide (37) and (Z)-2-methoxy-3-(4-methoxyphenyl)-N-p-tolylacrylamide (38) exhibited potent immunosuppressive activity (IC50 = 1.77 +/- 0.33 and 0.94 +/- 0.13 mu M) without significant cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.027
• 作为产物：
  描述：

  对氯苯乙腈 在 硫酸 、 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 3-(4-chlorophenyl)-2-oxopropionic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of analogues of butyrolactone I and molecular model of its interaction with CDK2

  摘要：

  一系列丁酯内酯I的类似物被合成，该天然产物是从土曲霉（Aspergillus terreus）中分离出来的，能够选择性抑制CDK2和CDK1激酶，并且已被发现表现出有趣的抗增殖活性。其抗肿瘤活性已被测试。通过结合构象搜索和自动对接技术构建了丁酯内酯I与CDK2活性位点之间复合物的分子模型。通过分子动态模拟评估了所得到复合物的稳定性，并基于分子模型对合成类似物获得的实验结果进行了合理化分析。

  DOI：

  10.1039/b403052d

文献信息

• A novel synthetic protocol for the synthesis of <i>pulvinones,</i> and naturally occurring <i>Aspulvinone E</i>, molecules of medicinal interest
  作者：Kyriakos C. Prousis、Sotirios Katsamakas、John Markopoulos、Olga Igglessi-Markopoulou

  DOI：10.1080/00397911.2021.2001662

  日期：2022.1.2

  Abstract A novel two step methodology for readily accessible natural “pulvinone” derivatives in excellent yields has been developed starting from activated precursors, bearing a functionalized 1,3-dioxolane-2,4-diones (OCA’s), as dually protected-activated synthons of α-hydroxy acids. The present procedure is based on a tandem C-acylation-cyclization process under mild conditions with good yields.

  摘要 一种新颖的两步方法，用于以优异的收率获得易于获得的天然“pulvinone”衍生物，从活化前体开始，带有功能化的 1,3-二氧戊环-2,4-二酮 (OCA)，作为 α 的双重保护活化合成子-羟基酸。本程序基于在温和条件下以良好收率进行的串联 C-酰化-环化过程。此外，pulvinones 显示出重要的药用特征，其中 tetronate 杂环表现出良好的药代动力学 (PK) 和 ADME-Tox 特性，由于合成限制，迄今为止可被认为尚未开发。
• An<i>Atropos</i>Biphenyl Bisphosphine Ligand with 2,2′-<i>tert</i>-Butylmethylphosphino Groups for the Rhodium-Catalyzed Asymmetric Hydrogenation of Enol Esters
  作者：Jia Jia、Dongyang Fan、Jian Zhang、Zhenfeng Zhang、Wanbin Zhang

  DOI：10.1002/adsc.201800774

  日期：2018.10.4

  calculations described in our previous work. This P‐stereogenic bisphosphine ligand possessing a biphenyl backbone and 2,2′‐tert‐butylmethylphosphino groups has been applied to the Rh‐catalyzed asymmetric hydrogenation of enol esters, which has not been widely studied and can be used for the synthesis of several important bioactive compounds. Although there is room for further improvement in enantioselectivity

  这是我们先前有关Atropos联苯双膦配体开发的工作的更新。单晶X射线衍射证实了Atropos出乎意料的结构性能，该结果与我们先前工作中所述的计算结果相符。这种具有联苯骨架和2,2'-叔丁基甲基膦基的P-stereogenic bisphosphine配体已被用于Rh催化的烯醇酯的不对称加氢反应，尚未得到广泛研究，可用于合成几种重要的生物活性化合物。尽管在对映选择性方面仍有进一步改进的余地，但本文报道的结果提供了对这类配体的进一步理解。
• Enantioselective synthesis of non-natural amino acids using phenylalanine dehydrogenases modified by site-directed mutagenesis
  作者：Patricia Busca、Francesca Paradisi、Eamonn Moynihan、Anita R. Maguire、Paul C. Engel

  DOI：10.1039/b406364c

  日期：——

  The substrate scope of three mutants of phenylalanine dehydrogenase as biocatalysts for the transformation of a series of 2-oxo acids, structurally related to phenylpyruvic acid, to the analogous α-amino acids, non-natural analogues of phenylalanine, has been investigated. The mutant enzymes are more tolerant than the wild type enzyme of the non-natural substrates, especially those with substituents at the 4-position on the phenyl ring. Excellent enantiocontrol resulted in all cases.

  三个变种的苯丙氨酸脱氢酶作为生物催化剂，用于将一系列与苯丙酮酸结构相关的2-氧酸转化为相应的α-氨基酸，即苯丙氨酸的非天然类似物，其底物范围已被研究。这些变种酶比野生型酶更能容忍非天然底物，特别是那些在苯环的4-位有取代基的底物。在所有情况下，都表现出了优秀的对映选择性。
• 5-(α-Halobenzyl)- and 5-Benzylidene-2,2-dimethyl-1,3-oxazolidin-4-ones in Synthesis of α-Hydroxy Acids
  作者：V. A. Mamedov、V. L. Mamedova、G. Z. Khikmatova、D. E. Korshin、O. G. Sinyashin

  DOI：10.1134/s1070363217120088

  日期：2017.12

  The reactions of acid hydrolysis of 5-(α-halobenzyl)- and 5-benzylidene-2,2-dimethyl-1,3-oxazolidin-4-ones were studied. A possibility of the synthesis of corresponding α-hydroxy acids was shown.

  研究了5-（α-卤代苄基）-和5-亚苄基-2,2-二甲基-1,3-恶唑烷丁-4-酮的酸水解反应。显示了合成相应的α-羟基酸的可能性。
• Method of treating resistant tumors
  申请人：Wyeth Holdings Corporation

  公开号：US20040121965A1

  公开（公告）日：2004-06-24

  The invention provides a method of treating or inhibiting the growth of or eradicating a tumor in a mammal in need thereof wherein said tumor is resistant to at least one chemotherapeutic agent which method comprises providing to said mammal an effective amount of a compound of Formula II or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制哺乳动物体内对至少一种化疗药物产生耐药性的肿瘤生长或根除肿瘤的方法，该方法包括向该哺乳动物提供有效量的公式II化合物或其药学上可接受的盐。

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