(2R)-1-(3-chloro-2-methylphenyl)sulfonylpiperidine-2-carboxylic acid | 1472657-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-1-(3-chloro-2-methylphenyl)sulfonylpiperidine-2-carboxylic acid
• CAS: 1472657-63-8
• 化学式: C₁₃H₁₆ClNO₄S
• 分子量: 317.793
• InChiKey: VQFVVBPVFOBFLS-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  七亚甲基亚胺 、 (2R)-1-(3-chloro-2-methylphenyl)sulfonylpiperidine-2-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (R)-azocan-1-yl(1-(3-chloro-2-methylphenylsulfonyl)piperidin-2-yl)methanone
  参考文献：
  名称：

  Design and Synthesis of (R)-1-Arylsulfonylpiperidine-2-carboxamides as 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors

  摘要：

  R adamantly beats S: 11β-HSD1 is a target for treating metabolic syndrome. The R isomer 5 was selected as a starting point for optimization and SAR studies. Inhibitor 8 w emerged after several rounds of optimization, showing cross-species inhibition of human and mouse 11β-HSD1. It also displays a good DMPK profile in vitro, and was advanced to PK/PD evaluations in vivo. The results confirmed its dose-dependent activity in mice.

  DOI：

  10.1002/cmdc.201300022
• 作为产物：
  描述：

  3-氯-2-甲基苯磺酰氯 在 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 (2R)-1-(3-chloro-2-methylphenyl)sulfonylpiperidine-2-carboxylic acid
  参考文献：
  名称：

  Design and Synthesis of (R)-1-Arylsulfonylpiperidine-2-carboxamides as 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors

  摘要：

  R adamantly beats S: 11β-HSD1 is a target for treating metabolic syndrome. The R isomer 5 was selected as a starting point for optimization and SAR studies. Inhibitor 8 w emerged after several rounds of optimization, showing cross-species inhibition of human and mouse 11β-HSD1. It also displays a good DMPK profile in vitro, and was advanced to PK/PD evaluations in vivo. The results confirmed its dose-dependent activity in mice.

  DOI：

  10.1002/cmdc.201300022