(E)-3-Phenyl-acrylic acid 1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl ester | 748812-30-8

• 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: (E)-3-Phenyl-acrylic acid 1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl ester
• 英文别名: (1,3-dioxoisoindol-2-yl)methyl (E)-3-phenylprop-2-enoate
• CAS: 748812-30-8
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: NIJJDJGSTXBRTN-ZHACJKMWSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  480.2±28.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)
• 溶解度：
  2.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-羟甲基邻苯二甲酰亚胺 、 肉桂酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以12%的产率得到(E)-3-Phenyl-acrylic acid 1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl ester
  参考文献：
  名称：

  Flavonoids and cinnamic acid esters as inhibitors of fungal 17β-hydroxysteroid dehydrogenase: A synthesis, QSAR and modelling study

  摘要：

  The 17 beta-hydroxysteroid dehydrogenases (17 beta-HSDs) modulate the biological potency of estrogens and androgens by interconversion of inactive 17-keto-steroids and their active 17 beta-hydroxy- counterparts. We have shown previously that flavonoids are potentially useful lead compounds for developing inhibitors of 17 beta-HSDs. In this paper, we describe the synthesis and biochemical evaluation of structurally analogous inhibitors, the trans-cinnamic acid esters and related compounds. Additionally, quantitative structure-activity relationship (QSAR) and modelling studies were performed to rationalize the results and to suggest further optimization. The results stress the importance of a hydrogen bond with Asn154 and hydrophobic interactions with the aromatic side chain of Tyr212 for optimal molecular recognition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.027