(S)-N-((S)-3-amino-1-cyano-3-oxopropyl)-1-((2’-chloro-[1,1’-biphenyl]-4-yl)sulfonyl)pyrrolidine-2-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-N-((S)-3-amino-1-cyano-3-oxopropyl)-1-((2’-chloro-[1,1’-biphenyl]-4-yl)sulfonyl)pyrrolidine-2-carboxamide
• 英文别名: (2S)-N-[(1S)-3-amino-1-cyano-3-oxopropyl]-1-[4-(2-chlorophenyl)phenyl]sulfonylpyrrolidine-2-carboxamide
• 化学式: C₂₁H₂₁ClN₄O₄S
• 分子量: 460.941
• InChiKey: QOYZFGUHQQASLP-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (S)-1-((4-bromophenyl)sulfonyl)pyrrolidine-2-carboxylate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三聚氯氰 、 水 、 sodium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 (S)-N-((S)-3-amino-1-cyano-3-oxopropyl)-1-((2’-chloro-[1,1’-biphenyl]-4-yl)sulfonyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Development of a potent and selective cell penetrant Legumain inhibitor

  摘要：

  This Letter describes the continued SAR exploration of small molecule Legumain inhibitors with the aim of developing a potent and selective in vitro tool compound. Work continued in this Letter explores the use of alternative P2-P3 linker units and the P3 group SAR which led to the identification of 10t, a potent, selective and cellularly active Legumain inhibitor. We also demonstrate that 10t has activity in both cancer cell viability and colony formation assays. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.001

文献信息

• Development of a potent and selective cell penetrant Legumain inhibitor
  作者：Kerry A. Ness、Sharon L. Eddie、Catherine A. Higgins、Amy Templeman、Zenobia D’Costa、Kishore K.D. Gaddale、Samira Bouzzaoui、Linda Jordan、Dominic Janssen、Timothy Harrison、Frank Burkamp、Andrew Young、Roberta Burden、Christopher J. Scott、Paul B. Mullan、Rich Williams

  DOI：10.1016/j.bmcl.2015.10.001

  日期：2015.12

  This Letter describes the continued SAR exploration of small molecule Legumain inhibitors with the aim of developing a potent and selective in vitro tool compound. Work continued in this Letter explores the use of alternative P2-P3 linker units and the P3 group SAR which led to the identification of 10t, a potent, selective and cellularly active Legumain inhibitor. We also demonstrate that 10t has activity in both cancer cell viability and colony formation assays. (C) 2015 Elsevier Ltd. All rights reserved.