2-[1-(2-chloro-phenyl)-ethylamino]-5-isopropyl-thiazol-4-one | 927175-28-8

• 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: 2-[1-(2-chloro-phenyl)-ethylamino]-5-isopropyl-thiazol-4-one
• CAS: 927175-28-8
• 化学式: C₁₄H₁₇ClN₂OS
• 分子量: 296.821
• InChiKey: BAJMZEDPOWOCCX-QHGLUPRGSA-N

物化性质

• 沸点：
  401.0±47.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[1-(2-chloro-phenyl)-ethylamino]-5-isopropyl-thiazol-4-one 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 以43%的产率得到2-[1-(2-chloro-phenyl)-ethylamino]-5-isopropyl-5-methyl-thiazol-4-one
  参考文献：
  名称：

  2-(S)-Phenethylaminothiazolones as Potent, Orally Efficacious Inhibitors of 11β-Hydroxysteriod Dehydrogenase Type 1

  摘要：

  11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) is the enzyme that converts cortisone to cortisol. A growing body of evidence suggests that selective inhibition of 11 beta-HSD1 could potentially treat metabolic syndrome as well as type 2 diabetes. Through modification of our initial lead 1, we have discovered trifluoromethyl thiazolone 17. This compound had a K-i of 22 nM, possessed low in vivo clearance, and showed a 91% inhibition of adipose 11 beta-HSD1 enzymatic activity in a mouse ex vivo pharmacodynamic model.

  DOI：

  10.1021/jm061214f
• 作为产物：
  描述：

  1-benzoyl-3-[1-(2-chloro-phenyl)-ethyl]-thiourea 在 氢氧化钾 、 sodium acetate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 2-[1-(2-chloro-phenyl)-ethylamino]-5-isopropyl-thiazol-4-one
  参考文献：
  名称：

  2-(S)-Phenethylaminothiazolones as Potent, Orally Efficacious Inhibitors of 11β-Hydroxysteriod Dehydrogenase Type 1

  摘要：

  11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) is the enzyme that converts cortisone to cortisol. A growing body of evidence suggests that selective inhibition of 11 beta-HSD1 could potentially treat metabolic syndrome as well as type 2 diabetes. Through modification of our initial lead 1, we have discovered trifluoromethyl thiazolone 17. This compound had a K-i of 22 nM, possessed low in vivo clearance, and showed a 91% inhibition of adipose 11 beta-HSD1 enzymatic activity in a mouse ex vivo pharmacodynamic model.

  DOI：

  10.1021/jm061214f