2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl 2-oxo-2H-chromene-3-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl 2-oxo-2H-chromene-3-carboxylate
• 英文别名: 2-(1,3-dioxoisoindol-2-yl)ethyl 2-oxochromene-3-carboxylate
• 化学式: C₂₀H₁₃NO₆
• 分子量: 363.326
• InChiKey: LRKDHUNEOQYOOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-羟乙基酞酰亚胺 、 香豆素-3-羧酸 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10%的产率得到2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl 2-oxo-2H-chromene-3-carboxylate
  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

文献信息

• Flavonoids and cinnamic acid esters as inhibitors of fungal 17β-hydroxysteroid dehydrogenase: A synthesis, QSAR and modelling study
  作者：Matej Sova、Andrej Perdih、Miha Kotnik、Katja Kristan、Tea Lanišnik Rižner、Tom Solmajer、Stanislav Gobec

  DOI：10.1016/j.bmc.2006.07.027

  日期：2006.11

  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.