(3S)-4-cyclohexyl-2-hydroxy-3-<<(2S)-4-methyl-2-<<(2S)-2-(3-oxohexahydro-3H-pyrrolo<1,2-c>imidazol-2-yl)-3-phenylpropionyl>amino>pentanoyl>amino>butyric acid isopropyl ester | 137282-05-4

• 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: (3S)-4-cyclohexyl-2-hydroxy-3-<<(2S)-4-methyl-2-<<(2S)-2-(3-oxohexahydro-3H-pyrrolo<1,2-c>imidazol-2-yl)-3-phenylpropionyl>amino>pentanoyl>amino>butyric acid isopropyl ester
• 英文别名: (3S)-4-cyclohexyl-2-hydroxy-3-[((2S)-4-methyl-2-{[(2S)-2-(3-oxohexahydro-3H-pyrrolo[1,2-c]imidazol-2-yl)-3-phenylpropionyl]amino}pentanoyl)amino]butyric acid isopropyl ester；propan-2-yl (3S)-4-cyclohexyl-2-hydroxy-3-[[(2S)-4-methyl-2-[[(2S)-2-(3-oxo-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2-yl)-3-phenylpropanoyl]amino]pentanoyl]amino]butanoate
• CAS: 137282-05-4；139236-19-4；139236-26-3
• 化学式: C₃₄H₅₂N₄O₆
• 分子量: 612.81
• InChiKey: IDAGTJFHGXSVCC-XOYGGWQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  44.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  128.28
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (2S)-2-<<<(1S)-1-(methoxycarbonyl)-2-phenylethyl>amino>methyl>pyrrolidine-1-carboxylic acid tert-butyl ester 在 sodium hydroxide 、 1-环已基-2-吗啉乙基碳二亚胺对甲苯磺酸盐 、 1-羟基苯并三唑 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (3S)-4-cyclohexyl-2-hydroxy-3-<<(2S)-4-methyl-2-<<(2S)-2-(3-oxohexahydro-3H-pyrrolo<1,2-c>imidazol-2-yl)-3-phenylpropionyl>amino>pentanoyl>amino>butyric acid isopropyl ester
  参考文献：
  名称：

  New modified heterocyclic phenylalanine derivatives. Incorporation into potent inhibitors of human renin

  摘要：

  Modified heterocyclic phenylalanine analogues designed as replacements for the P3-P4 region were synthesized and incorporated into renin inhibitors. These inhibitors were found to have significant activity versus human recombinant renin, as well as in vivo activity. The compounds proved to be very resistant to chymotrypsin degradation, as exemplified by compound 8, which remained greater than 60% intact after a 24-h exposure to chymotrypsin. In contrast, the Boc-Phe analogue was nearly completely degraded after 1 h. Compound 6 proved to be the most potent renin inhibitor with an IC50 = 8.9 nM. These stable cyclized phenylalanines should prove to be generally useful as a substitute for Boc-Phe in protease inhibitors.

  DOI：

  10.1021/jm00083a005