(E)-2-(4-chlorophenyl)-3-(4-methylsulfanylphenyl)prop-2-enoic acid | 1430809-14-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(4-chlorophenyl)-3-(4-methylsulfanylphenyl)prop-2-enoic acid
• CAS: 1430809-14-5
• 化学式: C₁₆H₁₃ClO₂S
• 分子量: 304.797
• InChiKey: KPLSEFPHWMHXKU-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-chlorophenyl)-3-(4-methylsulfanylphenyl)prop-2-enoic acid 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以73%的产率得到(E)-2-(4-chlorophenyl)-3-(4-methylsulfonylphenyl)prop-2-enoic acid
  参考文献：
  名称：

  2,3-Diarylpropenoic acids as selective non-steroidal inhibitors of type-5 17β-hydroxysteroid dehydrogenase (AKR1C3)

  摘要：

  The aldo-keto reductase AKR1C3 is an important target for the development of new drugs. Selective inhibitors of this enzyme are needed because they should not inhibit other, structurally closely related AKR1C isoforms. A comprehensive series of 2,3-diarylpropenoic acids was synthesized and evaluated for the inhibition of AKR1C1-AKR1C3. We found that the 4-methylsulfonylphenyl substituent at position 2 of these acids is required to exhibit the selective inhibition of AKR1C3. The best results were obtained for the compounds that fulfill the above requirement and possess a 4-bromophenyl, 4-methylthiophenyl, 4-methylphenyl or 4-ethylphenyl substituent at position 3 of the substituted propenoic acids (i.e., acids 28, 29, 37, and 39, respectively). These compounds represent an important step toward the development of drug candidates for a treatment of the hormone-dependent and hormone-independent forms of prostate and breast cancers. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.045
• 作为产物：
  描述：

  对氯苯乙酸 、 4-(甲基巯基)苯甲醛 在 乙酸酐 、 三乙胺 作用下， 反应 6.0h， 以55%的产率得到(E)-2-(4-chlorophenyl)-3-(4-methylsulfanylphenyl)prop-2-enoic acid
  参考文献：
  名称：

  2,3-Diarylpropenoic acids as selective non-steroidal inhibitors of type-5 17β-hydroxysteroid dehydrogenase (AKR1C3)

  摘要：

  The aldo-keto reductase AKR1C3 is an important target for the development of new drugs. Selective inhibitors of this enzyme are needed because they should not inhibit other, structurally closely related AKR1C isoforms. A comprehensive series of 2,3-diarylpropenoic acids was synthesized and evaluated for the inhibition of AKR1C1-AKR1C3. We found that the 4-methylsulfonylphenyl substituent at position 2 of these acids is required to exhibit the selective inhibition of AKR1C3. The best results were obtained for the compounds that fulfill the above requirement and possess a 4-bromophenyl, 4-methylthiophenyl, 4-methylphenyl or 4-ethylphenyl substituent at position 3 of the substituted propenoic acids (i.e., acids 28, 29, 37, and 39, respectively). These compounds represent an important step toward the development of drug candidates for a treatment of the hormone-dependent and hormone-independent forms of prostate and breast cancers. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.045

文献信息

• Substituted thiazoles for the treatment of inflammation
  申请人：G.D. SEARLE & CO.

  公开号：EP1125932A2

  公开（公告）日：2001-08-22

  A class of substituted thiazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II wherein R4 is selected from methyl and amino; wherein R5 is selected from optionally substituted aryl, cycloalkyl, cycloalkenyl and heterocyclic; and wherein R6 is selected from hydrogen or specified substituents; or a pharmaceutically-acceptable salt thereof.

  描述了一类用于治疗炎症和炎症相关疾病的取代噻唑化合物。特别感兴趣的化合物由式 II 定义 其中 R4 选自甲基和氨基；其中 R5 选自任选取代的芳基、环烷基、环烯基和杂环基；其中 R6 选自氢或特定取代基；或其药学上可接受的盐。
• US5668161A
  申请人：——

  公开号：US5668161A

  公开（公告）日：1997-09-16
• 2,3-Diarylpropenoic acids as selective non-steroidal inhibitors of type-5 17β-hydroxysteroid dehydrogenase (AKR1C3)
  作者：Martin Gazvoda、Nataša Beranič、Samo Turk、Bojan Burja、Marijan Kočevar、Tea Lanišnik Rižner、Stanislav Gobec、Slovenko Polanc

  DOI：10.1016/j.ejmech.2012.12.045

  日期：2013.4

  The aldo-keto reductase AKR1C3 is an important target for the development of new drugs. Selective inhibitors of this enzyme are needed because they should not inhibit other, structurally closely related AKR1C isoforms. A comprehensive series of 2,3-diarylpropenoic acids was synthesized and evaluated for the inhibition of AKR1C1-AKR1C3. We found that the 4-methylsulfonylphenyl substituent at position 2 of these acids is required to exhibit the selective inhibition of AKR1C3. The best results were obtained for the compounds that fulfill the above requirement and possess a 4-bromophenyl, 4-methylthiophenyl, 4-methylphenyl or 4-ethylphenyl substituent at position 3 of the substituted propenoic acids (i.e., acids 28, 29, 37, and 39, respectively). These compounds represent an important step toward the development of drug candidates for a treatment of the hormone-dependent and hormone-independent forms of prostate and breast cancers. (C) 2013 Elsevier Masson SAS. All rights reserved.