5,6-bis(benzyloxy)-1-oxo-2-propyl-2-indanpropionic acid | 68935-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5,6-bis(benzyloxy)-1-oxo-2-propyl-2-indanpropionic acid
• 英文别名: 1H-Indene-2-propanoicacid, 2,3-dihydro-1-oxo-5,6-bis(phenylmethoxy)-2-propyl-；3-[3-oxo-5,6-bis(phenylmethoxy)-2-propyl-1H-inden-2-yl]propanoic acid
• CAS: 68935-40-0
• 化学式: C₂₉H₃₀O₅
• 分子量: 458.554
• InChiKey: NBZBRMBEAWOCAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-bis(benzyloxy)-1-oxo-2-propyl-2-indanpropionic acid 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 480.0h， 以67%的产率得到5,6-bis(benzyloxy)-1-hydroxy-2-propyl-2-indanpropionic acid
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of indanpropionic acids as uterine relaxants

  摘要：

  The PGF2 alpha antagonist 5,6-bis(benzyloxy)-1-oxo-2-propyl-2-indanpropionic acid (1) had previously been shown to provide significant protection against the abortifacient actions of PGF2 alpha in mice. To explore further structural concepts in drug design employed for the development of 1, several mono(benzyloxy) ketones (3-10) and alcohols (11-15) as well as a diacid (22) were prepared. None of these structural modifications resulted in compounds of greater superiority to 1 as uterine relaxants and 22 was void of any antagonistic properties, suggesting that the original rationale requiring one carboxyl group and two benzyloxy functions appropriately placed for maximum PGF2 alpha antagonism in this series was a good assumption. A carbonyl rather than hydroxyl group at position C-1 of the indan is most beneficial for reversible antagonism. Reduction of the ketone to the alcohol is of synthetic interest and discussed in some detail.

  DOI：

  10.1021/jm00375a023

文献信息

• Synthesis and pharmacological evaluation of indanpropionic acids as uterine relaxants
  作者：Donald T. Witiak、Ahmed M. Hassan、Franziska R. Del Vecchio、Richard J. Brumbaugh、Ralf G. Rahwan

  DOI：10.1021/jm00375a023

  日期：1984.9

  The PGF2 alpha antagonist 5,6-bis(benzyloxy)-1-oxo-2-propyl-2-indanpropionic acid (1) had previously been shown to provide significant protection against the abortifacient actions of PGF2 alpha in mice. To explore further structural concepts in drug design employed for the development of 1, several mono(benzyloxy) ketones (3-10) and alcohols (11-15) as well as a diacid (22) were prepared. None of these structural modifications resulted in compounds of greater superiority to 1 as uterine relaxants and 22 was void of any antagonistic properties, suggesting that the original rationale requiring one carboxyl group and two benzyloxy functions appropriately placed for maximum PGF2 alpha antagonism in this series was a good assumption. A carbonyl rather than hydroxyl group at position C-1 of the indan is most beneficial for reversible antagonism. Reduction of the ketone to the alcohol is of synthetic interest and discussed in some detail.