(2S,4R)-4-(5-Cyano-pyridin-2-ylamino)-2-((S)-2-cyano-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 401564-60-1

• 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: (2S,4R)-4-(5-Cyano-pyridin-2-ylamino)-2-((S)-2-cyano-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 401564-60-1
• 化学式: C₂₁H₂₆N₆O₃
• 分子量: 410.476
• InChiKey: JSIUNQSYSGVITR-IKGGRYGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  122.35
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-(5-Cyano-pyridin-2-ylamino)-2-((S)-2-cyano-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 6-[(3R,5S)-5-((S)-2-Cyano-pyrrolidine-1-carbonyl)-pyrrolidin-3-ylamino]-nicotinonitrile
  参考文献：
  名称：

  1-((S)-γ-Substituted prolyl)-(S)-2-cyanopyrrolidine as a novel series of highly potent DPP-IV inhibitors

  摘要：

  1-(gamma-Substituted prolyl)-(S)-2-cyanopyrrolidines were designed based on the predicted binding mode of the known DPP-IV inhibitor NVP-DPP728 and evaluated for their inhibitory activity. In structure-activity relationship study at the gamma-position of proline, it became clear that compounds bearing (S)-stereochemistry were 20-fold more potent than the antipode. Of these compounds, the (3,4-dicyanophenyl)amino- and (3-chloro-4-cyanophenyl)amino-derivatives showed the highest inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.077
• 作为产物：
  描述：

  methyl (2S,4R)-1-tert-butoxycarbonyl-4-(5-cyano-pyridin-2-ylamino)pyrrolidine-2-carboxylate 在 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 生成 (2S,4R)-4-(5-Cyano-pyridin-2-ylamino)-2-((S)-2-cyano-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  1-((S)-γ-Substituted prolyl)-(S)-2-cyanopyrrolidine as a novel series of highly potent DPP-IV inhibitors

  摘要：

  1-(gamma-Substituted prolyl)-(S)-2-cyanopyrrolidines were designed based on the predicted binding mode of the known DPP-IV inhibitor NVP-DPP728 and evaluated for their inhibitory activity. In structure-activity relationship study at the gamma-position of proline, it became clear that compounds bearing (S)-stereochemistry were 20-fold more potent than the antipode. Of these compounds, the (3,4-dicyanophenyl)amino- and (3-chloro-4-cyanophenyl)amino-derivatives showed the highest inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.077