(E)-3-(1-tert-butoxycarbonyl-3-oxo-2-phenylpyrazolidin-4-ylidenemethyl)-4,6-dichloro-1H-indole-2-carboxylic acid | 166974-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-3-(1-tert-butoxycarbonyl-3-oxo-2-phenylpyrazolidin-4-ylidenemethyl)-4,6-dichloro-1H-indole-2-carboxylic acid
• 英文别名: 4,6-dichloro-3-[(E)-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3-oxo-2-phenylpyrazolidin-4-ylidene]methyl]-1H-indole-2-carboxylic acid
• CAS: 166974-27-2
• 化学式: C₂₄H₂₁Cl₂N₃O₅
• 分子量: 502.354
• InChiKey: FSSAAZLYSXNXBH-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(1-tert-butoxycarbonyl-3-oxo-2-phenylpyrazolidin-4-ylidenemethyl)-4,6-dichloro-1H-indole-2-carboxylic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到4,6-dichloro-3-(5-oxo-1-phenylpyrazolidin-4-ylidenemethyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists

  摘要：

  After the identification of GV150526, the indole-2-carboxylate template was further explored in order to identify novel potential anti-stroke agents. In particular, the SAR of the side chain present at the C-3 position of the indole nucleus was widely studied. In this paper, the synthesis and the pharmacological profile of a further class of conformationally restricted analogues of GV150526 as in vitro and in vivo potent glycine antagonists is reported. In particular, a pyrazolidinone derivative was identified as a potent neuroprotective agent in animal models of cerebral ischaemia. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01141-7
• 作为产物：
  描述：

  4,6-二氯-3-甲酰基-1H-吲哚-2-甲酸乙酯 在 4-二甲氨基吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (E)-3-(1-tert-butoxycarbonyl-3-oxo-2-phenylpyrazolidin-4-ylidenemethyl)-4,6-dichloro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and pharmacological characterisation of a conformationally restrained series of indole-2-carboxylates as in vivo potent glycine antagonists

  摘要：

  After the identification of GV150526, the indole-2-carboxylate template was further explored in order to identify novel potential anti-stroke agents. In particular, the SAR of the side chain present at the C-3 position of the indole nucleus was widely studied. In this paper, the synthesis and the pharmacological profile of a further class of conformationally restricted analogues of GV150526 as in vitro and in vivo potent glycine antagonists is reported. In particular, a pyrazolidinone derivative was identified as a potent neuroprotective agent in animal models of cerebral ischaemia. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01141-7