[(1S)-1-(2-fluorophenyl)ethyl]thiourea | 927175-31-3

• 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: [(1S)-1-(2-fluorophenyl)ethyl]thiourea
• CAS: 927175-31-3
• 化学式: C₉H₁₁FN₂S
• 分子量: 198.264
• InChiKey: CUEHDKNJUPWBAE-LURJTMIESA-N

物化性质

• 沸点：
  296.4±42.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(1S)-1-(2-fluorophenyl)ethyl]thiourea 在 sodium acetate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正庚烷 、 乙基苯 为溶剂， 反应 3.58h， 生成 2-((S)-1-(2-fluorophenyl)ethylamino)-5-(2-hydroxypropan-2-yl)-5-methylthiazol-4(5H)-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：

  (S)-1-(2-氟苯基)乙胺 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 [(1S)-1-(2-fluorophenyl)ethyl]thiourea
  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

文献信息

• 2-(<i>S</i>)-Phenethylaminothiazolones as Potent, Orally Efficacious Inhibitors of 11β-Hydroxysteriod Dehydrogenase Type 1
  作者：David J. St. Jean,、Chester Yuan、Eric A. Bercot、Rod Cupples、Michelle Chen、Jenne Fretland、Clarence Hale、Randall W. Hungate、Renee Komorowski、Murielle Veniant、Minghan Wang、Xiping Zhang、Christopher Fotsch

  DOI：10.1021/jm061214f

  日期：2007.2.8

  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.