6,7-Dihydroxy-1-(4-trifluoromethyl-benzoyl)-isoquinoline-3-carboxylic acid | 597543-80-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 6,7-Dihydroxy-1-(4-trifluoromethyl-benzoyl)-isoquinoline-3-carboxylic acid
• 英文别名: 6,7-dihydroxy-1-[4-(trifluoromethyl)benzoyl]isoquinoline-3-carboxylic acid
• CAS: 597543-80-1
• 化学式: C₁₈H₁₀F₃NO₅
• 分子量: 377.276
• InChiKey: JUTGUXZPCAMMMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6,7-Dihydroxy-1-(4-trifluoromethyl-benzoyl)-isoquinoline-3-carboxylic acid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 6,7-Dihydroxy-1-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-isoquinoline-3-carboxylic acid
  参考文献：
  名称：

  6,7-Dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-Like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain

  摘要：

  A series of 1-benzoyl isoquinolines, based on compound 1, was synthesized and evaluated for their ability to displace IGF-I from its complex with IGF-binding protein-3. Successful modifications of I included the replacement of the 3,4-dihydroxy-benzoyl group with a substituted benzyl group. These alternations culminated in the discovery of compounds such as 7o which had excellent in vitro potency (K-i = 9.4 nM) but with one less of the labile catechol functionality of 1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00321-4
• 作为产物：
  描述：

  6,7-Bis-benzyloxy-1-(4-trifluoromethyl-benzyl)-isoquinoline-3-carboxylic acid benzyl ester 在 selenium(IV) oxide 、 氢气 、 溶剂黄146 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 生成 6,7-Dihydroxy-1-(4-trifluoromethyl-benzoyl)-isoquinoline-3-carboxylic acid
  参考文献：
  名称：

  6,7-Dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-Like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain

  摘要：

  A series of 1-benzoyl isoquinolines, based on compound 1, was synthesized and evaluated for their ability to displace IGF-I from its complex with IGF-binding protein-3. Successful modifications of I included the replacement of the 3,4-dihydroxy-benzoyl group with a substituted benzyl group. These alternations culminated in the discovery of compounds such as 7o which had excellent in vitro potency (K-i = 9.4 nM) but with one less of the labile catechol functionality of 1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00321-4