{(S)-1-[(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(3-methyl-butylamino)-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester | 108868-79-7

• 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: {(S)-1-[(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(3-methyl-butylamino)-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• 英文别名: {1-[1-[1-Cyclohexylmethyl-2-hydroxy-4-(3-methyl-butylamino)-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester；tert-butyl N-[(2S)-1-[[(2S)-1-[[(2S,3S)-1-cyclohexyl-3-hydroxy-5-(3-methylbutylamino)pentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 108868-79-7
• 化学式: C₃₆H₅₈N₆O₅
• 分子量: 654.894
• InChiKey: WLIIIXJGJDXNEA-YDPTYEFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基-2-丙基[(2S)-1-环己基-3-氧代-2-丙基]氨基甲酸酯 在 palladium on activated charcoal 、 镍 N-甲基吗啉 、 盐酸 、 5A molecular sieve 、 氨 、 氢气 、 sodium cyanoborohydride 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、303.98 kPa 条件下， 反应 125.92h， 生成 {(S)-1-[(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(3-methyl-butylamino)-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Novel renin inhibitors containing analogs of statine retro-inverted at the C-termini. Specificity at the P2 histidine site

  摘要：

  Substituted 1,3- and 1,4-diamines were prepared from epoxides derived from Boc-leucine or Boc-cyclohexylalanine. These diamines were incorporated into renin inhibitors (IC50 = 4-1500 nM) replacing the Leu-Val scissile bond in small peptide analogues of angiotensinogen. Replacement of the P2 histidine imidazole with other heterocycles maintained or enhanced binding while changing the overall basicity of the inhibitor. Finally, substitution of O-methyltyrosine for the P3 phenylalanine suppressed chymotrypsin cleavage of the P3-P2 bond.

  DOI：

  10.1021/jm00390a018

文献信息

• Novel renin inhibitors containing analogs of statine retro-inverted at the C-termini. Specificity at the P2 histidine site
  作者：Saul H. Rosenberg、Jacob J. Plattner、Keith W. Woods、Herman H. Stein、Patrick A. Marcotte、Jerome Cohen、Thomas J. Perun

  DOI：10.1021/jm00390a018

  日期：1987.7

  Substituted 1,3- and 1,4-diamines were prepared from epoxides derived from Boc-leucine or Boc-cyclohexylalanine. These diamines were incorporated into renin inhibitors (IC50 = 4-1500 nM) replacing the Leu-Val scissile bond in small peptide analogues of angiotensinogen. Replacement of the P2 histidine imidazole with other heterocycles maintained or enhanced binding while changing the overall basicity of the inhibitor. Finally, substitution of O-methyltyrosine for the P3 phenylalanine suppressed chymotrypsin cleavage of the P3-P2 bond.