(R)-methyl 1-(3-chloro-2-methylphenylsulfonyl)-N-cyclohexylpiperidine-2-carboxylate | 1472657-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-methyl 1-(3-chloro-2-methylphenylsulfonyl)-N-cyclohexylpiperidine-2-carboxylate
• 英文别名: methyl (2R)-1-(3-chloro-2-methylphenyl)sulfonylpiperidine-2-carboxylate
• CAS: 1472657-62-7
• 化学式: C₁₄H₁₈ClNO₄S
• 分子量: 331.82
• InChiKey: PUOMZJUYVRRWHR-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methyl 1-(3-chloro-2-methylphenylsulfonyl)-N-cyclohexylpiperidine-2-carboxylate 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 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 (R)-1-(3-chloro-2-methylphenylsulfonyl)-N-((1S,2R,3S,5R)-3,6,6-trimethylbicyclo[3.1.1]heptan-2-yl)piperidine-2-carboxamide
  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 、 (R)-哌啶-2-甲酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以99%的产率得到(R)-methyl 1-(3-chloro-2-methylphenylsulfonyl)-N-cyclohexylpiperidine-2-carboxylate
  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

文献信息

• Design and Synthesis of (<i>R</i>)-1-Arylsulfonylpiperidine-2-carboxamides as 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors
  作者：Guangxin Xia、Lin Liu、Haiyan Liu、Jianxin Yu、Zhenmin Xu、Qian Chen、Chen Ma、Ping Li、Bing Xiong、Xuejun Liu、Jingkang Shen

  DOI：10.1002/cmdc.201300022

  日期：2013.4

  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.