methyl 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylate | 93503-51-6

• 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: methyl 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylate
• 英文别名: methyl 4-(2-phenyl-1H-indol-3-yl)cyclohex-3-ene-1-carboxylate
• CAS: 93503-51-6
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: AWWMJVNMXOCUGW-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  533.2±50.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylate 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 26.75h， 生成 4-(1-methyl-2-phenyl-1H-indol-3-yl)-benzoic acid
  参考文献：
  名称：

  Syntheses and complement inhibitory activities of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids

  摘要：

  The syntheses of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids are described. These compounds express potent in vitro inhibition of the human classical complement pathway, and qualitative SAR have been determined. Several of the in vitro active compounds also suppressed the complement dependent reverse passive Arthus reaction (RPAR) in guinea pigs.

  DOI：

  10.1021/jm00380a002
• 作为产物：
  描述：

  4-羰基环己羧酸 在 磷酸 、 乙酸酐 、 potassium carbonate 、 溶剂黄146 作用下， 反应 78.0h， 生成 methyl 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylate
  参考文献：
  名称：

  Syntheses and complement inhibitory activities of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids

  摘要：

  The syntheses of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids are described. These compounds express potent in vitro inhibition of the human classical complement pathway, and qualitative SAR have been determined. Several of the in vitro active compounds also suppressed the complement dependent reverse passive Arthus reaction (RPAR) in guinea pigs.

  DOI：

  10.1021/jm00380a002

文献信息

• 2-Phenylindole derivatives, their use as complement inhibitors
  申请人：Sterling Drug Inc.

  公开号：US04510158A1

  公开（公告）日：1985-04-09

  4-(1-R'-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acids, 4-(1'R'-2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids, 4-(1-R'-2-phenyl-1H-indol-3-yl)benzoic acids, the corresponding cyclohexene- and cyclohexane-1,1-dicarboxylic acids, and lower-alkyl esters thereof, wherein R' is hydrogen or lower-alkyl, are prepared by reacting a 1-R'-2-phenyl-1H-indole with a cyclohexanone-4-carboxylic acid or -4,4-dicarboxylic acid, followed as desired by a hydrogenation or aromatization process. The compounds which are free carboxylic acids or salts thereof are useful as complement inhibitors. The corresponding esters are useful as intermediates.

  通过将1-R'-2-苯基-1H-吲哚与环己酮-4-羧酸或-4,4-二羧酸反应，然后根据需要进行氢化或芳构化处理，制备4-(1-R'-2-苯基-1H-吲哚-3-基)-3-环己烯-1-羧酸、4-(1'R'-2-苯基-1H-吲哚-3-基)环己烷-1-羧酸、4-(1-R'-2-苯基-1H-吲哚-3-基)苯甲酸，相应的环己烯-和环己烷-1,1-二羧酸以及它们的低烷基酯。其中R'是氢或低烷基。这些化合物中的游离羧酸或其盐可用作补体抑制剂。相应的酯可用作中间体。
• BAILEY, D. M.;DEGRAZIA, G. D.;ALEXANDER, E. J.;POWLES, R. G.;JOHNSON, R. +, J. MED. CHEM., 1985, 28, N 2, 160-164
  作者：BAILEY, D. M.、DEGRAZIA, G. D.、ALEXANDER, E. J.、POWLES, R. G.、JOHNSON, R. +

  DOI：——

  日期：——
• US4510158A
  申请人：——

  公开号：US4510158A

  公开（公告）日：1985-04-09