(S)-2,3-dihydro-2-(4-ethyl-1H-imidazol-2-yl)-1H-indole | 480423-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2,3-dihydro-2-(4-ethyl-1H-imidazol-2-yl)-1H-indole
• 英文别名: (S)-2-(5-Ethyl-1H-imidazol-2-yl)indoline；(2S)-2-(5-ethyl-1H-imidazol-2-yl)-2,3-dihydro-1H-indole
• CAS: 480423-36-7
• 化学式: C₁₃H₁₅N₃
• 分子量: 213.282
• InChiKey: HLMZQXTXYVUGHN-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2,3-dihydro-2-(4-ethyl-1H-imidazol-2-yl)-1H-indole 在 N-甲基吗啉 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 0.75h， 生成 (S)-2-Amino-1-[(S)-2-(5-ethyl-1H-imidazol-2-yl)-2,3-dihydro-indol-1-yl]-propan-1-one
  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 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 5.58h， 生成 (S)-2,3-dihydro-2-(4-ethyl-1H-imidazol-2-yl)-1H-indole
  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

文献信息

• Tripeptidyl-peptidase II (TPP II) inhibitory activity of ( S )-2,3-dihydro-2-(1 H -imidazol-2-yl)-1 H -indoles, a systematic SAR evaluation. Part 2
  作者：Henry J. Breslin、Tamara A. Miskowski、Michael J. Kukla、Hans L. De Winter、Maria V.F. Somers、Peter W.M. Roevens、Robert W. Kavash

  DOI：10.1016/j.bmcl.2003.09.014

  日期：2003.12

  We have systematically explored the structure-activity relationship (SAR) for a series of compounds 2 as inhibitors of tripeptidyl-peptidase II (TPP II), a serine protease responsible for the degradation of cholecystokinin-8 (CCK-8). This SAR evaluation of the core structure 2 suggest a fairly restrictive pharmacophore for such related structures, but has yielded a limited set of compounds (2b, 2c, 2d, 2s, and 2t) with potent TPP II inhibitory activity (IC50 4-11 nM). (C) 2003 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Tripeptidyl Peptidase II Inhibitory Activity of a Novel Series of (<i>S</i>)-2,3-Dihydro-2-(4-alkyl-1<i>H</i>-imidazol-2-yl)-1<i>H</i>-indoles
  作者：Henry J. Breslin、Tamara A. Miskowski、Michael J. Kukla、William H. Leister、Hans L. De Winter、Diane A. Gauthier、Maria V. F. Somers、Daniëlle C. G. Peeters、Peter W. M. Roevens

  DOI：10.1021/jm0202831

  日期：2002.11.1

  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.