(3R,4S)-Piperidine-1,3,4-tricarboxylic acid 1,3-diallyl ester 4-tert-butyl ester | 252919-36-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (3R,4S)-Piperidine-1,3,4-tricarboxylic acid 1,3-diallyl ester 4-tert-butyl ester
• CAS: 252919-36-1
• 化学式: C₁₈H₂₇NO₆
• 分子量: 353.415
• InChiKey: MUIFEPXYORIMPL-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-Piperidine-1,3,4-tricarboxylic acid 1,3-diallyl ester 4-tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(3R,4S)-Piperidine-1,3,4-tricarboxylic acid 1,3-diallyl ester
  参考文献：
  名称：

  Rational design, synthesis and structure–activity relationships of a cyclic succinate series of TNF-α converting enzyme inhibitors. Part 2: lead optimization

  摘要：

  Modifications of the lead TACE inhibitor 1 (N-hydroxy-trans-2-{[4-(4-quinolinyloxymethyl)anilinyl]carbonyl}-1-cyclo-hexanecarboxamide) at the cyclohexyl ring and the quinoline moiety led to the identification of a series of piperidine containing TACE inhibitors with potent activity in the inhibition of TNF-alpha release in the whole blood assay (WBA). The most potent analogue IM491 [N-hydroxy-(5S,6S)-1-methyl-6-{[4-(2-methyl-4-quinolinylmethoxy)anilinyl]carbonyl}-5-piperidinecarboxamide] exhibited an IC50 value of 20 nM in WBA with excellent selectivity over MMP-1, -2 and -9 and is orally bioavailable with an F value of 43% in beagle dogs. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.057
• 作为产物：
  描述：

  (3R,4S)-4-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid 在 N-甲基吗啉 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成 (3R,4S)-Piperidine-1,3,4-tricarboxylic acid 1,3-diallyl ester 4-tert-butyl ester
  参考文献：
  名称：

  Rational design, synthesis and structure–activity relationships of a cyclic succinate series of TNF-α converting enzyme inhibitors. Part 2: lead optimization

  摘要：

  Modifications of the lead TACE inhibitor 1 (N-hydroxy-trans-2-{[4-(4-quinolinyloxymethyl)anilinyl]carbonyl}-1-cyclo-hexanecarboxamide) at the cyclohexyl ring and the quinoline moiety led to the identification of a series of piperidine containing TACE inhibitors with potent activity in the inhibition of TNF-alpha release in the whole blood assay (WBA). The most potent analogue IM491 [N-hydroxy-(5S,6S)-1-methyl-6-{[4-(2-methyl-4-quinolinylmethoxy)anilinyl]carbonyl}-5-piperidinecarboxamide] exhibited an IC50 value of 20 nM in WBA with excellent selectivity over MMP-1, -2 and -9 and is orally bioavailable with an F value of 43% in beagle dogs. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.057