[2S-[1(R*),R*]]-{1-[2-(4-propyl-1H-imidazol-2-yl)-2,3-dihydroindole-1-carbonyl]propyl}carbamic acid tert-butyl ester | 422573-46-4

• 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: [2S-[1(R*),R*]]-{1-[2-(4-propyl-1H-imidazol-2-yl)-2,3-dihydroindole-1-carbonyl]propyl}carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-oxo-1-[(2S)-2-(5-propyl-1H-imidazol-2-yl)-2,3-dihydroindol-1-yl]butan-2-yl]carbamate
• CAS: 422573-46-4
• 化学式: C₂₃H₃₂N₄O₃
• 分子量: 412.532
• InChiKey: XYLJGBPUCOYCIS-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  87.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2S-[1(R*),R*]]-{1-[2-(4-propyl-1H-imidazol-2-yl)-2,3-dihydroindole-1-carbonyl]propyl}carbamic acid tert-butyl ester 在 三氟乙酸 、 盐酸 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以19%的产率得到[2S-[1(R*),R*]]-α-ethyl-2,3-dihydro-β-oxo-2-(4-propyl-1H-imidazol-2-yl)-1H-indole-1-ethanamine hydrochloride
  参考文献：
  名称：

  Design, Synthesis, and Tripeptidyl Peptidase II Inhibitory Activity of a Novel Series of (S)-2,3-Dihydro-2-(4-alkyl-1H-imidazol-2-yl)-1H-indoles

  摘要：

  Butabindide, 1, was previously reported as a potent inhibitor (IC50 = 7 nM) of the serine protease enzyme tripeptidyl peptidase II (TPPII), an endogenous protease that degrades cholecystokinin-8 (CCK-8). We found that 1 has some inherent chemical instability, yielding diketopiperazine 2 fairly readily under mimicked physiological conditions. We therefore prepared imidazoles 3, which are void of 1's inherent instability, and have found that our novel analogues maintained comparable TPPII inhibitory activity (e.g.,for 3c, IC50 = 4 nM) as 1.

  DOI：

  10.1021/jm0202831
• 作为产物：
  描述：

  (S)-吲哚啉-2-羧酸 在 N-甲基吗啉 、 盐酸 、 氯化亚砜 、 氨 、 potassium acetate 、 三乙胺 、 三氯乙酰氯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 6.08h， 生成 [2S-[1(R*),R*]]-{1-[2-(4-propyl-1H-imidazol-2-yl)-2,3-dihydroindole-1-carbonyl]propyl}carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, Synthesis, and Tripeptidyl Peptidase II Inhibitory Activity of a Novel Series of (S)-2,3-Dihydro-2-(4-alkyl-1H-imidazol-2-yl)-1H-indoles

  摘要：

  Butabindide, 1, was previously reported as a potent inhibitor (IC50 = 7 nM) of the serine protease enzyme tripeptidyl peptidase II (TPPII), an endogenous protease that degrades cholecystokinin-8 (CCK-8). We found that 1 has some inherent chemical instability, yielding diketopiperazine 2 fairly readily under mimicked physiological conditions. We therefore prepared imidazoles 3, which are void of 1's inherent instability, and have found that our novel analogues maintained comparable TPPII inhibitory activity (e.g.,for 3c, IC50 = 4 nM) as 1.

  DOI：

  10.1021/jm0202831