(3-Methyl-but-2-enyl)-phenyl-piperidin-4-yl-amine | 288573-58-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (3-Methyl-but-2-enyl)-phenyl-piperidin-4-yl-amine
• CAS: 288573-58-0
• 化学式: C₁₆H₂₄N₂
• 分子量: 244.38
• InChiKey: RHYKCFNVKGIUPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.27
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,3-二甲基丁醛 、 (3-Methyl-but-2-enyl)-phenyl-piperidin-4-yl-amine 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 1-(3,3-dimethylbutyl)-N-(3-methylbut-2-enyl)-N-phenylpiperidin-4-amine
  参考文献：
  名称：

  The discovery of [1-(4-dimethylamino-benzyl)-piperidin-4-yl]-[4-(3,3-dimethylbutyl)-phenyl]-(3-methyl-but-2-enyl)-amine, an N-type Ca +2 channel blocker with oral activity for analgesia

  摘要：

  Our drug discovery efforts for N-type calcium channel blockers in the 4-piperidinylaniline series led to the discovery of an orally active analgesic agent 26. 1-[4-Dimethylamino-benzyl)-piperidin-4-yl]-[4-(3,3-dimethyl-butyl)-phenyl]-(3-methyl-but-2-enyl)-amine (26) showed high affinity to functionally block N-type calcium channels IC50 = 0.7 mu M in the IMR32 assay) and exhibited high efficacy in the anti-writhing analgesia test with mice (ED50 = 12 mg/kg by po and 4 mg/kg by iv). In this report, the rationale for the design, synthesis, biological evaluation, and pharmacokinetics of this series of blockers is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00077-8
• 作为产物：
  描述：

  4-phenylimino-piperidine-1-carboxylic acid tert-butyl ester 在 三乙酰氧基硼氢化钠 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.17h， 生成 (3-Methyl-but-2-enyl)-phenyl-piperidin-4-yl-amine
  参考文献：
  名称：

  The discovery of [1-(4-dimethylamino-benzyl)-piperidin-4-yl]-[4-(3,3-dimethylbutyl)-phenyl]-(3-methyl-but-2-enyl)-amine, an N-type Ca +2 channel blocker with oral activity for analgesia

  摘要：

  Our drug discovery efforts for N-type calcium channel blockers in the 4-piperidinylaniline series led to the discovery of an orally active analgesic agent 26. 1-[4-Dimethylamino-benzyl)-piperidin-4-yl]-[4-(3,3-dimethyl-butyl)-phenyl]-(3-methyl-but-2-enyl)-amine (26) showed high affinity to functionally block N-type calcium channels IC50 = 0.7 mu M in the IMR32 assay) and exhibited high efficacy in the anti-writhing analgesia test with mice (ED50 = 12 mg/kg by po and 4 mg/kg by iv). In this report, the rationale for the design, synthesis, biological evaluation, and pharmacokinetics of this series of blockers is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00077-8

文献信息

• Structure-activity relationship at the proximal phenyl group in a series of non-peptidyl N-type calcium channel antagonists
  作者：Todd R. Ryder、Lain-Yen Hu、Michael F. Rafferty、Susan M. Lotarski、David M. Rock、Sally J. Stoehr、Charles P. Taylor、Mark L. Weber、George P. Miljanich、Elizabeth Millerman、Balazs G. Szoke

  DOI：10.1016/s0960-894x(99)00405-9

  日期：1999.8

  Selective N-Type Voltage Sensitive Calcium Channel (VSCC) antagonists have shown utility in several models of pain and ischemia. We report the structure-activity relationship at the proximal phenyl group in a series of non-peptidyl VSCC blockers, (C) 1999 Published by Elsevier Science Ltd. All rights reserved.