BMS-354326 | 708258-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: BMS-354326
• 英文别名: 2-Azetidinecarboxylic acid, 4-oxo-1-((4-(1-oxo-6-phenylhexyl)-1-piperazinyl)carbonyl)-3-(2-(3-piperidinyl)ethyl)-, (2S,3R)-；(2S,3R)-4-oxo-1-[4-(6-phenylhexanoyl)piperazine-1-carbonyl]-3-(2-piperidin-3-ylethyl)azetidine-2-carboxylic acid
• CAS: 708258-16-6
• 化学式: C₂₈H₄₀N₄O₅
• 分子量: 512.649
• InChiKey: XVYFBYVSZOCXRJ-OMQKAAQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(2-碘乙基)哌啶-1-甲酸叔丁酯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 TEA 、 四丁基氟化铵 、 氢气 、 碳酸氢钠 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 BMS-354326
  参考文献：
  名称：

  Synthesis of potent and highly selective nonguanidine azetidinone inhibitors of human tryptase

  摘要：

  Azetidinones such as BMS-363131 (2) and BMS-363130 (3), which contain a guanidine group in the C-3 side chain were previously shown to be very potent inhibitors of human tryptase with high selectivity versus other serine proteases, including trypsin. In this letter, we describe the discovery of a number of potent azetidinone tryptase inhibitors in which the guanidine moiety at the ring C-3 position is replaced with primary or secondary amine or aminopyridine functionality. In particular, BMS-354326 (4) is a highly potent tryptase inhibitor (IC50 1.8 nM), which has excellent selectivity against trypsin and most other related serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.011

文献信息

• Synthesis of potent and highly selective nonguanidine azetidinone inhibitors of human tryptase
  作者：Gregory S Bisacchi、William A Slusarchyk、Scott A Bolton、Karen S Hartl、Glenn Jacobs、Arvind Mathur、Wei Meng、Martin L Ogletree、Zulan Pi、James C Sutton、Uwe Treuner、Robert Zahler、Guohua Zhao、Steven M Seiler

  DOI：10.1016/j.bmcl.2004.02.011

  日期：2004.5

  Azetidinones such as BMS-363131 (2) and BMS-363130 (3), which contain a guanidine group in the C-3 side chain were previously shown to be very potent inhibitors of human tryptase with high selectivity versus other serine proteases, including trypsin. In this letter, we describe the discovery of a number of potent azetidinone tryptase inhibitors in which the guanidine moiety at the ring C-3 position is replaced with primary or secondary amine or aminopyridine functionality. In particular, BMS-354326 (4) is a highly potent tryptase inhibitor (IC50 1.8 nM), which has excellent selectivity against trypsin and most other related serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.