(S)-3-(4-Amino-phenyl)-2-[((R)-2-benzenesulfonyl-2-aza-bicyclo[2.2.2]octane-3-carbonyl)-amino]-propionic acid methyl ester | 887904-71-4

• 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: (S)-3-(4-Amino-phenyl)-2-[((R)-2-benzenesulfonyl-2-aza-bicyclo[2.2.2]octane-3-carbonyl)-amino]-propionic acid methyl ester
• CAS: 887904-71-4
• 化学式: C₂₄H₂₉N₃O₅S
• 分子量: 471.577
• InChiKey: XRHMEYXVXNLSSZ-JFHVBQFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  118.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-Amino-phenyl)-2-[((R)-2-benzenesulfonyl-2-aza-bicyclo[2.2.2]octane-3-carbonyl)-amino]-propionic acid methyl ester 在 lithium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-2-[((R)-2-Benzenesulfonyl-2-aza-bicyclo[2.2.2]octane-3-carbonyl)-amino]-3-[4-(2,6-dichloro-benzoylamino)-phenyl]-propionic 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：

  2-Benzenesulfonyl-2-aza-bicyclo[2.2.2]octane-3-carboxylic acid ethyl ester 在 lithium hydroxide 、 氯化铵 、 1-羟基苯并三唑 、 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 (S)-3-(4-Amino-phenyl)-2-[((R)-2-benzenesulfonyl-2-aza-bicyclo[2.2.2]octane-3-carbonyl)-amino]-propionic acid methyl ester
  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