6-chloro-N-cyclohexyl-2-propoxynicotinamide | 1024038-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-chloro-N-cyclohexyl-2-propoxynicotinamide
• 英文别名: 6-chloro-N-cyclohexyl-2-propoxypyridine-3-carboxamide
• CAS: 1024038-80-9
• 化学式: C₁₅H₂₁ClN₂O₂
• 分子量: 296.797
• InChiKey: ZYYCAWACACKIJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-N-cyclohexyl-2-propoxynicotinamide 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 丁腈 为溶剂， 反应 20.0h， 生成 2-[(3S)-1-[5-(cyclohexylcarbamoyl)-6-(methylpropylamino)pyridin-2-yl]-3-piperidyl]acetic acid
  参考文献：
  名称：

  Discovery of a Potent, Selective, and Orally Bioavailable Acidic 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Inhibitor: Discovery of 2-[(3S)-1-[5-(Cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-3-piperidyl]acetic Acid (AZD4017)

  摘要：

  Inhibition of 11 beta-HSD1 is an attractive mechanism for the treatment of obesity and other elements of the metabolic syndrome. We report here the discovery of a nicotinic amide derived carboxylic acid class of inhibitors that has good potency, selectivity, and pharmacokinetic characteristics. Compound 11i (AZD4017) is an effective inhibitor of 11 beta-HSD1 in human adipocytes and exhibits good druglike properties and as a consequence was selected for clinical development.

  DOI：

  10.1021/jm300592r
• 作为产物：
  描述：

  2,6-二氯烟酸 在 氯化亚砜 、 sodium hexamethyldisilazane 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 6-chloro-N-cyclohexyl-2-propoxynicotinamide
  参考文献：
  名称：

  Discovery of a Potent, Selective, and Orally Bioavailable Acidic 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) Inhibitor: Discovery of 2-[(3S)-1-[5-(Cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-3-piperidyl]acetic Acid (AZD4017)

  摘要：

  Inhibition of 11 beta-HSD1 is an attractive mechanism for the treatment of obesity and other elements of the metabolic syndrome. We report here the discovery of a nicotinic amide derived carboxylic acid class of inhibitors that has good potency, selectivity, and pharmacokinetic characteristics. Compound 11i (AZD4017) is an effective inhibitor of 11 beta-HSD1 in human adipocytes and exhibits good druglike properties and as a consequence was selected for clinical development.

  DOI：

  10.1021/jm300592r

文献信息

• CHEMICAL COMPOUNDS
  申请人：McCoull William

  公开号：US20080269288A1

  公开（公告）日：2008-10-30

  Compounds of formula (I): wherein variable groups are defined within; their use in the inhibition of 11βHSD1, processes for making them and pharmaceutical compositions comprising them are described.

  公式（I）的化合物：其中变量基团在内部定义；描述了它们在抑制11βHSD1中的应用，制备它们的过程以及包含它们的药物组合物。
• PYRIDINE CARBOXAMIDES AS 11-BETA-HSD1 INHIBITORS
  申请人：AstraZeneca AB

  公开号：EP2086939B8

  公开（公告）日：2011-06-22
• Chemical compounds
  申请人：AstraZeneca AB

  公开号：EP2233480B1

  公开（公告）日：2013-05-29
• US7964618B2
  申请人：——

  公开号：US7964618B2

  公开（公告）日：2011-06-21
• US8673938B2
  申请人：——

  公开号：US8673938B2

  公开（公告）日：2014-03-18