(2R,3S)-3-Amino-4-cyclohexyl-1-(pyridin-2-ylsulfanyl)-butan-2-ol | 1053628-52-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R,3S)-3-Amino-4-cyclohexyl-1-(pyridin-2-ylsulfanyl)-butan-2-ol
• 英文别名: (2R,3S)-3-amino-4-cyclohexyl-1-pyridin-2-ylsulfanylbutan-2-ol
• CAS: 1053628-52-6
• 化学式: C₁₅H₂₄N₂OS
• 分子量: 280.434
• InChiKey: UFYCNAQFQOIKIG-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-Amino-4-cyclohexyl-1-(pyridin-2-ylsulfanyl)-butan-2-ol 在 氨 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 20.5h， 生成 (2S,3S)-3-(Boc-Phe-His-amino)-4-cyclohexyl-1-(2-pyridylthio)-2-butanol
  参考文献：
  名称：

  Renin inhibitors containing C-termini derived from mercaptoheterocycles

  摘要：

  A series of transition-state analogues having heterocyclylthio C-termini has been synthesized and evaluated for inhibition of human renin. Addition of mercaptoheterocycles to a chiral Boc-amino epoxide intermediate led, after several steps, to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. Oxidation of the thioether to sulfone was also investigated. Several of the compounds, especially those derived from N1-substituted-5-mercaptotetrazoles or N4-substituted-3-mercapto-5-(trifluoromethyl)-1,2,4-triazoles, were moderately potent inhibitors of human plasma renin, having IC50 values of 30-40 nM. When selected compounds were administered intravenously to sodium-deficient rhesus monkeys at 0.3-1.2 mg/kg, they reduced plasma renin activity by 75-98%. However, this inhibition and the accompanying drop in blood pressure were of short duration.

  DOI：

  10.1021/jm00089a023
• 作为产物：
  描述：

  (2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane 在 盐酸 、 四氯化锡 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 (2R,3S)-3-Amino-4-cyclohexyl-1-(pyridin-2-ylsulfanyl)-butan-2-ol
  参考文献：
  名称：

  Renin inhibitors containing C-termini derived from mercaptoheterocycles

  摘要：

  A series of transition-state analogues having heterocyclylthio C-termini has been synthesized and evaluated for inhibition of human renin. Addition of mercaptoheterocycles to a chiral Boc-amino epoxide intermediate led, after several steps, to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. Oxidation of the thioether to sulfone was also investigated. Several of the compounds, especially those derived from N1-substituted-5-mercaptotetrazoles or N4-substituted-3-mercapto-5-(trifluoromethyl)-1,2,4-triazoles, were moderately potent inhibitors of human plasma renin, having IC50 values of 30-40 nM. When selected compounds were administered intravenously to sodium-deficient rhesus monkeys at 0.3-1.2 mg/kg, they reduced plasma renin activity by 75-98%. However, this inhibition and the accompanying drop in blood pressure were of short duration.

  DOI：

  10.1021/jm00089a023

文献信息

• Renin inhibitors containing C-termini derived from mercaptoheterocycles
  作者：Wallace T. Ashton、Christine L. Cantone、Laura C. Meurer、Richard L. Tolman、William J. Greenlee、Arthur A. Patchett、Robert J. Lynch、Terry W. Schorn、John F. Strouse、Peter K. S. Siegl

  DOI：10.1021/jm00089a023

  日期：1992.5

  A series of transition-state analogues having heterocyclylthio C-termini has been synthesized and evaluated for inhibition of human renin. Addition of mercaptoheterocycles to a chiral Boc-amino epoxide intermediate led, after several steps, to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. Oxidation of the thioether to sulfone was also investigated. Several of the compounds, especially those derived from N1-substituted-5-mercaptotetrazoles or N4-substituted-3-mercapto-5-(trifluoromethyl)-1,2,4-triazoles, were moderately potent inhibitors of human plasma renin, having IC50 values of 30-40 nM. When selected compounds were administered intravenously to sodium-deficient rhesus monkeys at 0.3-1.2 mg/kg, they reduced plasma renin activity by 75-98%. However, this inhibition and the accompanying drop in blood pressure were of short duration.