2,4-dimethylpentan-3-yl 4-[(3R,4S)-3-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methyl]-2-oxo-4-phenylmethoxycarbonylazetidine-1-carbonyl]piperazine-1-carboxylate | 705950-80-7

• 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: 2,4-dimethylpentan-3-yl 4-[(3R,4S)-3-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methyl]-2-oxo-4-phenylmethoxycarbonylazetidine-1-carbonyl]piperazine-1-carboxylate
• CAS: 705950-80-7
• 化学式: C₃₅H₅₂N₄O₈
• 分子量: 656.82
• InChiKey: ALNCZLSXATXVHU-IZLXSDGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4-dimethylpentan-3-yl 4-[(3R,4S)-3-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methyl]-2-oxo-4-phenylmethoxycarbonylazetidine-1-carbonyl]piperazine-1-carboxylate 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 4-((2S,3R)-2-Carboxy-4-oxo-3-piperidin-4-ylmethyl-azetidine-1-carbonyl)-piperazine-1-carboxylic acid 1-isopropyl-2-methyl-propyl ester
  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
• 作为产物：
  描述：

  1-diisopropylmethoxycarbonylpiperazine-4-carbonylchloride 、 tert-butyl 4-[[(3R,4S)-2-oxo-4-phenylmethoxycarbonylazetidin-3-yl]methyl]piperidine-1-carboxylate 在 4-二甲氨基吡啶 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以87%的产率得到2,4-dimethylpentan-3-yl 4-[(3R,4S)-3-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methyl]-2-oxo-4-phenylmethoxycarbonylazetidine-1-carbonyl]piperazine-1-carboxylate
  参考文献：
  名称：

  Beta lactam compounds and their use as inhibitors of tryptase

  摘要：

  提供了具有以下结构的β-内酰胺化合物 1 其中B、A、D、R 1 、R 2 、R 3 和X 1 如本文所定义，并且这些化合物可用作组胺酶、凝血酶、胰蛋白酶、Xa因子、VIIa因子和尿激酶型纤溶酶原激活剂的抑制剂，并可用于预防和/或治疗哮喘和过敏性鼻炎。

  公开号：

  US20040147502A1