rac-3-allyl [4-(2-ethylphenyl)-2-phenyl-1-N-(3-pyridylmethyl)-2,3-dehydro-piperidin-3-yl]carboxylate | 923002-43-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: rac-3-allyl [4-(2-ethylphenyl)-2-phenyl-1-N-(3-pyridylmethyl)-2,3-dehydro-piperidin-3-yl]carboxylate
• CAS: 923002-43-1
• 化学式: C₂₉H₃₀N₂O₂
• 分子量: 438.569
• InChiKey: PRGAZMPPYSXLPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  42.43
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  rac-3-allyl [4-(2-ethylphenyl)-2-phenyl-1-N-(3-pyridylmethyl)-2,3-dehydro-piperidin-3-yl]carboxylate 在 盐酸 、 lithium aluminium tetrahydride 、 氯化亚砜 、 水 、 溴甲酚绿 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.0h， 生成 rac-(2S,3S,4R)-4-(2-ethylphenyl)-3-hydroxymethyl-2-phenyl-1-N-(3-pyridylmethyl)-piperidine
  参考文献：
  名称：

  Design and synthesis of piperidine farnesyltransferase inhibitors with reduced glucuronidation potential

  摘要：

  The design and synthesis of a novel piperidine series of farnesyltransferase (FTase) inhibitors with reduced potential for metabolic glucuronidation are described. The various substitution and exchange of the phenyl group at the C-2 position of the previously described 2-(4-hydroxy)phenyl-3-nitropiperidine 1a (FTase IC50 = 5.4 nM) resulted in metabolically stable compounds with potent FTase inhibition (14a IC50 = 4.3 nM, 20a IC50 = 3.0 nM, and 50a IC50 = 16 nM). Molecular modeling studies of these compounds complexed with FTasc and farnesyl pyrophosphate are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.007
• 作为产物：
  描述：

  丙-2-烯-1-基3-羰基-3-苯基丙酸酯 在 lithium salt of proline 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 48.0h， 生成 rac-3-allyl [4-(2-ethylphenyl)-2-phenyl-1-N-(3-pyridylmethyl)-2,3-dehydro-piperidin-3-yl]carboxylate
  参考文献：
  名称：

  Design and synthesis of piperidine farnesyltransferase inhibitors with reduced glucuronidation potential

  摘要：

  The design and synthesis of a novel piperidine series of farnesyltransferase (FTase) inhibitors with reduced potential for metabolic glucuronidation are described. The various substitution and exchange of the phenyl group at the C-2 position of the previously described 2-(4-hydroxy)phenyl-3-nitropiperidine 1a (FTase IC50 = 5.4 nM) resulted in metabolically stable compounds with potent FTase inhibition (14a IC50 = 4.3 nM, 20a IC50 = 3.0 nM, and 50a IC50 = 16 nM). Molecular modeling studies of these compounds complexed with FTasc and farnesyl pyrophosphate are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.007