4-{1-[4-(Propane-2-sulfonyl)-phenyl]-ethylidene}-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester | 478958-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-{1-[4-(Propane-2-sulfonyl)-phenyl]-ethylidene}-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-[4-[1-(4-propan-2-ylsulfonylphenyl)ethylidene]piperidin-1-yl]piperidine-1-carboxylate
• CAS: 478958-06-4
• 化学式: C₂₆H₄₀N₂O₄S
• 分子量: 476.681
• InChiKey: HOTKNBOUXKRXFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-{1-[4-(Propane-2-sulfonyl)-phenyl]-ethylidene}-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到1-Piperidin-4-yl-4-[1-(4-propan-2-ylsulfonylphenyl)ethylidene]piperidine
  参考文献：
  名称：

  Improving the Oral Efficacy of CNS Drug Candidates:  Discovery of Highly Orally Efficacious Piperidinyl Piperidine M₂ Muscarinic Receptor Antagonists

  摘要：

  In search of a backup M-2 muscarinic receptor antagonist to the previously reported compound 1, we discovered compound (+)-14, which showed superior oral efficacy in animal models. The improvement of oral efficacy was achieved by modulating both the molecular weight and lipophilicity of the lead compounds.

  DOI：

  10.1021/jm0255163
• 作为产物：
  描述：

  4-(4-氟苯甲酰基)哌啶-1-甲酸叔丁酯 在 sodium perborate 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-{1-[4-(Propane-2-sulfonyl)-phenyl]-ethylidene}-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Improving the Oral Efficacy of CNS Drug Candidates:  Discovery of Highly Orally Efficacious Piperidinyl Piperidine M₂ Muscarinic Receptor Antagonists

  摘要：

  In search of a backup M-2 muscarinic receptor antagonist to the previously reported compound 1, we discovered compound (+)-14, which showed superior oral efficacy in animal models. The improvement of oral efficacy was achieved by modulating both the molecular weight and lipophilicity of the lead compounds.

  DOI：

  10.1021/jm0255163

文献信息

• Improving the Oral Efficacy of CNS Drug Candidates:  Discovery of Highly Orally Efficacious Piperidinyl Piperidine M₂ Muscarinic Receptor Antagonists
  作者：Yuguang Wang、Samuel Chackalamannil、Zhiyong Hu、William J. Greenlee、John Clader、Craig D. Boyle、James J. Kaminski、William Billard、Binch、Gordon Crosby、Vilma Ruperto、Ruth A. Duffy、Mary Cohen-Williams、Vicki L. Coffin、Kathleen A. Cox、Diane E. Grotz、Jean E. Lachowicz

  DOI：10.1021/jm0255163

  日期：2002.12.1

  In search of a backup M-2 muscarinic receptor antagonist to the previously reported compound 1, we discovered compound (+)-14, which showed superior oral efficacy in animal models. The improvement of oral efficacy was achieved by modulating both the molecular weight and lipophilicity of the lead compounds.