(2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-2-yl)-3-phenylpropionic acid | 137282-27-0

• 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: (2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-2-yl)-3-phenylpropionic acid
• 英文别名: (2S)-2-[1-oxo-2,3-dihydro-1H-benz(de)isoquinolin-2-yl]-3-phenylpropionic acid；(2S)-2-(3-oxo-1H-benzo[de]isoquinolin-2-yl)-3-phenylpropanoic acid
• CAS: 137282-27-0
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: YXNXFNIQVVASHA-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-2-yl)-3-phenylpropionic acid 、 (S)-3-((S)-2-Amino-4-methyl-pentanoylamino)-4-cyclohexyl-2-hydroxy-butyric acid isopropyl ester; compound with trifluoro-acetic acid 在 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 作用下， 生成 (3S)-4-cyclohexyl-2-hydroxy-3-<<(2S)-4-methyl-2-<<(2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-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
• 作为产物：
  描述：

  3-羟基-1H,3H-萘并[1,8-cd]吡喃-1-酮 在 盐酸 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 反应 0.08h， 生成 (2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-2-yl)-3-phenylpropionic acid
  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