(2Z)-(3-phenylpropylidene)succinic acid | 945414-56-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z)-(3-phenylpropylidene)succinic acid
• 英文别名: (3-phenyl-propylidene)-succinic acid；ε-Phenyl-β-amylen-α.β-dicarbonsaeure；γ-(β-Phenaethyl)-itaconsaeure；(3-Phenyl-propyliden)-bernsteinsaeure
• CAS: 945414-56-2
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: YMGGFEDVENVONG-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (3-phenyl-propenyl)-succinic acid 在 sodium hydroxide 作用下， 生成 (2Z)-(3-phenylpropylidene)succinic acid
  参考文献：
  名称：

  Fichter; Hirsch, Chemische Berichte, 1901, vol. 34, p. 2189

  摘要：

  DOI：

文献信息

• Simultaneous presence of unsaturation and long alkyl chain at <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" altimg="si10.gif" overflow="scroll"><mml:mrow><mml:msubsup><mml:mrow><mml:mtext>P</mml:mtext></mml:mrow><mml:mrow><mml:mn>1</mml:mn></mml:mrow><mml:mrow><mml:mo>′</mml:mo></mml:mrow></mml:msubsup></mml:mrow></mml:math> of Ilomastat confers selectivity for gelatinase A (MMP-2) over gelatinase B (MMP-9) inhibition as shown by molecular modelling studies
  作者：Gautier Moroy、Clément Denhez、Haquima El Mourabit、Alix Toribio、Alexandra Dassonville、Martine Decarme、Jean-Hugues Renault、Catherine Mirand、Georges Bellon、Janos Sapi、Alain J.P. Alix、William Hornebeck、Erika Bourguet

  DOI：10.1016/j.bmc.2007.05.001

  日期：2007.7

  Structural analogues of Ilomastat (Galardin (R)), containing unsaturation(s) and chain extension carrying bulky phenyl group or alkyl moieties at P-1(') were synthesized and purified by centrifugal partition chromatography. They were analyzed for their inhibitory capacity towards MMP-1, MMP-2, MMP-3, MMP-9 and MMP-14, main endopeptidases involved in tumour progression. Presence of unsaturation(s) decreased the inhibitory potency of compounds but, in turn increased their selectivity for gelatinases. 2b and 2d derivatives with a phenyl group inhibited preferentially MMP-9 with IC50 equal to 45 and 38 nM, respectively, but also display activity against MMP-2 IC50 equal to 280 and 120 nM, respectively). Molecular docking computations confirmed affinity of these substances for both gelatinases. With aims to obtain a specific gelatinase A (MMP-2) inhibitor, P, of Ilomastat was modified to carry one unsaturation coupled to an alkyl chain with pentylidene group. Docking studies indicated that MMP-2, but not MMP-9, could accommodate such substitution; indeed 2a proved to inhibit MMP-2 (IC50 = 123 nM), while displaying no inhibitory capacity towards MMP-9. (c) 2007 Elsevier Ltd. All rights reserved.