methyl (2S)-2-[[(3S)-2-(benzenesulfonyl)-2-azabicyclo[2.2.2]octane-3-carbonyl]amino]-3-[4-(1,3-dioxoisoindol-2-yl)phenyl]propanoate | 387337-39-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-[[(3S)-2-(benzenesulfonyl)-2-azabicyclo[2.2.2]octane-3-carbonyl]amino]-3-[4-(1,3-dioxoisoindol-2-yl)phenyl]propanoate
• CAS: 387337-39-5
• 化学式: C₃₂H₃₁N₃O₇S
• 分子量: 601.68
• InChiKey: ITNIDOUEVRPFAL-OWMKTDRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(3S)-2-(benzenesulfonyl)-2-azabicyclo[2.2.2]octane-3-carbonyl]amino]-3-[4-(1,3-dioxoisoindol-2-yl)phenyl]propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 N-(4-{(S)-2-[((S)-2-Benzenesulfonyl-2-aza-bicyclo[2.2.2]octane-3-carbonyl)-amino]-2-carboxy-ethyl}-phenyl)-phthalamic acid
  参考文献：
  名称：

  Aza-bicyclic amino acid sulfonamides as α4β1/α4β7 integrin antagonists

  摘要：

  The design, synthesis, and biological activity of novel alpha(4)beta(1) and alpha(4)beta(7) integrin antagonists, containing a bridged azabicyclic nucleus, are reported. Conformational analysis of targets containing an azabicyclo[2.2.2]octane carboxylic acid and known integrin antagonists indicated that this azabicycle would be a suitable molecular scaffold. Variation of substituents on the pendant arylsulfonamide and phenylalanine groups resulted in potent alpha(4)beta(1)-selective and dual alpha(4)beta(1)/alpha(4)beta(7) antagonists. Potent compounds 11i, 11h, and 14 were effective in the antigen-sensitized sheep model of asthma. (C) 2003 Elsevier Science Ltd. All rights reserved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.063
• 作为产物：
  描述：

  (S)-4-硝基苯丙氨酸甲酯 在 氯化铵 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl (2S)-2-[[(3S)-2-(benzenesulfonyl)-2-azabicyclo[2.2.2]octane-3-carbonyl]amino]-3-[4-(1,3-dioxoisoindol-2-yl)phenyl]propanoate
  参考文献：
  名称：

  Aza-bicyclic amino acid sulfonamides as α4β1/α4β7 integrin antagonists

  摘要：

  The design, synthesis, and biological activity of novel alpha(4)beta(1) and alpha(4)beta(7) integrin antagonists, containing a bridged azabicyclic nucleus, are reported. Conformational analysis of targets containing an azabicyclo[2.2.2]octane carboxylic acid and known integrin antagonists indicated that this azabicycle would be a suitable molecular scaffold. Variation of substituents on the pendant arylsulfonamide and phenylalanine groups resulted in potent alpha(4)beta(1)-selective and dual alpha(4)beta(1)/alpha(4)beta(7) antagonists. Potent compounds 11i, 11h, and 14 were effective in the antigen-sensitized sheep model of asthma. (C) 2003 Elsevier Science Ltd. All rights reserved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.063