(2S,3S)-1-(3,5-dichlorophenyl)sulfonyl-3-hydroxypyrrolidine-2-carboxylic acid | 425403-87-8

• 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: (2S,3S)-1-(3,5-dichlorophenyl)sulfonyl-3-hydroxypyrrolidine-2-carboxylic acid
• CAS: 425403-87-8
• 化学式: C₁₁H₁₁Cl₂NO₅S
• 分子量: 340.184
• InChiKey: FCERTUKRHFEZLI-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1-(3,5-dichlorophenyl)sulfonyl-3-hydroxypyrrolidine-2-carboxylic acid 在 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (2S)-2-[[(2S,3S)-1-(3,5-dichlorophenyl)sulfonyl-3-hydroxypyrrolidine-2-carbonyl]amino]-3-[4-(2-methoxyphenyl)phenyl]propanoic acid
  参考文献：
  名称：

  Specific and dual antagonists of α4β1 and α4β7 integrins

  摘要：

  N-(3,5-Dichlorophenylsulfonyl)-(R)-thioprolyl biarylalanine 10a has been identified as a potent and specific antagonist of the alpha(4)beta(1) integrin. Altering the configuration of thioproline from R to S led to a series of dual antagonists of alpha(4)beta(1) and alpha(4)beta(7), and the N-acetyl analogue 8b was found to be the most potent dual antagonist. A binding site model for alpha(4)beta(7) and alpha(4)beta(7) is proposed to explain the structure-activity relationship. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00705-3
• 作为产物：
  描述：

  3,5-二氯苯磺酰氯 、 反-3-羟基-L-脯氨酸 在 sodium carbonate 作用下， 以 水 为溶剂， 生成 (2S,3S)-1-(3,5-dichlorophenyl)sulfonyl-3-hydroxypyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Specific and dual antagonists of α4β1 and α4β7 integrins

  摘要：

  N-(3,5-Dichlorophenylsulfonyl)-(R)-thioprolyl biarylalanine 10a has been identified as a potent and specific antagonist of the alpha(4)beta(1) integrin. Altering the configuration of thioproline from R to S led to a series of dual antagonists of alpha(4)beta(1) and alpha(4)beta(7), and the N-acetyl analogue 8b was found to be the most potent dual antagonist. A binding site model for alpha(4)beta(7) and alpha(4)beta(7) is proposed to explain the structure-activity relationship. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00705-3

文献信息

• Specific and dual antagonists of α4β1 and α4β7 integrins
  作者：Linus S. Lin、Thomas Lanza、Ermenegilda McCauley、Gail Van Riper、Usha Kidambi、Jin Cao、Linda A. Egger、Richard A. Mumford、John A. Schmidt、Malcolm MacCoss、William K. Hagmann

  DOI：10.1016/s0960-894x(01)00705-3

  日期：2002.1

  N-(3,5-Dichlorophenylsulfonyl)-(R)-thioprolyl biarylalanine 10a has been identified as a potent and specific antagonist of the alpha(4)beta(1) integrin. Altering the configuration of thioproline from R to S led to a series of dual antagonists of alpha(4)beta(1) and alpha(4)beta(7), and the N-acetyl analogue 8b was found to be the most potent dual antagonist. A binding site model for alpha(4)beta(7) and alpha(4)beta(7) is proposed to explain the structure-activity relationship. (C) 2002 Elsevier Science Ltd. All rights reserved.