Pyrrolidine-1-carboxylic acid 4-((S)-2-{[(S)-1-(3,5-dichloro-benzenesulfonyl)-2-methyl-pyrrolidine-2-carbonyl]-amino}-2-methoxycarbonyl-ethyl)-phenyl ester | 217453-30-0

• 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: Pyrrolidine-1-carboxylic acid 4-((S)-2-{[(S)-1-(3,5-dichloro-benzenesulfonyl)-2-methyl-pyrrolidine-2-carbonyl]-amino}-2-methoxycarbonyl-ethyl)-phenyl ester
• CAS: 217453-30-0
• 化学式: C₂₇H₃₁Cl₂N₃O₇S
• 分子量: 612.531
• InChiKey: GUMUOMVUKANDJD-HOFKKMOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  122.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Pyrrolidine-1-carboxylic acid 4-((S)-2-{[(S)-1-(3,5-dichloro-benzenesulfonyl)-2-methyl-pyrrolidine-2-carbonyl]-amino}-2-methoxycarbonyl-ethyl)-phenyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 Pyrrolidine-1-carboxylic acid 4-((S)-2-carboxy-2-{[(S)-1-(3,5-dichloro-benzenesulfonyl)-2-methyl-pyrrolidine-2-carbonyl]-amino}-ethyl)-phenyl ester
  参考文献：
  名称：

  The discovery of small molecule carbamates as potent dual α4β1/α4β7 integrin antagonists

  摘要：

  The alpha(4)beta(1) and alpha(4)beta(7) integrins are implicated in several inflammatory disease states. Systematic SAR studies of an alpha(4)beta(1)-specific arylsulfonyl-Pro-Tyr lead led to the identification of a new alpha(4)beta(7) binding site, best captured by O-carbamates of Tyr for this structural class. Several compounds showed a 200- to 400-fold improvement in alpha(4)beta(7) binding affinity while maintaining subnanomolar alpha(4)beta(1) activity, for example 21, VCAM-Ig alpha(4)beta(1) IC50 = 0.13 nM. VCAM-Ig alpha(4)beta(7) IC50 = 1.92 nM. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00710-7
• 作为产物：
  描述：

  3,5-二氯苯磺酰氯 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 potassium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Pyrrolidine-1-carboxylic acid 4-((S)-2-{[(S)-1-(3,5-dichloro-benzenesulfonyl)-2-methyl-pyrrolidine-2-carbonyl]-amino}-2-methoxycarbonyl-ethyl)-phenyl ester
  参考文献：
  名称：

  The discovery of small molecule carbamates as potent dual α4β1/α4β7 integrin antagonists

  摘要：

  The alpha(4)beta(1) and alpha(4)beta(7) integrins are implicated in several inflammatory disease states. Systematic SAR studies of an alpha(4)beta(1)-specific arylsulfonyl-Pro-Tyr lead led to the identification of a new alpha(4)beta(7) binding site, best captured by O-carbamates of Tyr for this structural class. Several compounds showed a 200- to 400-fold improvement in alpha(4)beta(7) binding affinity while maintaining subnanomolar alpha(4)beta(1) activity, for example 21, VCAM-Ig alpha(4)beta(1) IC50 = 0.13 nM. VCAM-Ig alpha(4)beta(7) IC50 = 1.92 nM. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00710-7