(S)-Methyl 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate | 717815-15-1

• 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)-Methyl 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate
• 英文别名: methyl (2S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate
• CAS: 717815-15-1
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: FGLIVUIACOOOGS-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-Methyl 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate 在 lithium hydroxide 、 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 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-2-(2-Bromo-benzoylamino)-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid
  参考文献：
  名称：

  N-Benzoyl amino acids as LFA-1/ICAM inhibitors 1: amino acid structure–activity relationship

  摘要：

  The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00084-2
• 作为产物：
  描述：

  甲醇 、 (αS)-α-氨基-1H-吡咯并[2,3-b]吡啶-3-丙酸 在 盐酸 作用下， 反应 18.0h， 生成 (S)-Methyl 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate
  参考文献：
  名称：

  N-Benzoyl amino acids as LFA-1/ICAM inhibitors 1: amino acid structure–activity relationship

  摘要：

  The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00084-2

文献信息

• N-Benzoyl amino acids as LFA-1/ICAM inhibitors 1: amino acid structure–activity relationship
  作者：Daniel J. Burdick、Ken Paris、Kenneth Weese、Mark Stanley、Maureen Beresini、Kevin Clark、Robert S. McDowell、James C. Marsters、Thomas R. Gadek

  DOI：10.1016/s0960-894x(03)00084-2

  日期：2003.3

  The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid. (C) 2003 Elsevier Science Ltd. All rights reserved.