N-[(1R)-1-(4-chlorophenyl)ethyl]-2,2-dimethyl-N-[(E)-3-[(3S)-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-yl]prop-2-enyl]propanamide | 1529788-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: N-[(1R)-1-(4-chlorophenyl)ethyl]-2,2-dimethyl-N-[(E)-3-[(3S)-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-yl]prop-2-enyl]propanamide
• CAS: 1529788-23-5
• 化学式: C₃₀H₃₁ClN₄O₂
• 分子量: 515.055
• InChiKey: DYUUVBPOUOMLAV-HSCULCADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (6S)-3-amino-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 在 盐酸 、 N-甲基二环己基胺 、 bis(tributylphosphine)palladium 0 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(1R)-1-(4-chlorophenyl)ethyl]-2,2-dimethyl-N-[(E)-3-[(3S)-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-yl]prop-2-enyl]propanamide
  参考文献：
  名称：

  (E)-Alkenes as replacements of amide bonds: Development of novel and potent acyclic CGRP receptor antagonists

  摘要：

  A new class of CGRP receptor antagonists was identified by replacing the central amide of a previously identified anilide lead structure with ethylene, ethane, or ethyne linkers. (E)-Alkenes as well as alkynes were found to preserve the proper bioactive conformation of the amides, necessary for efficient receptor binding. Further exploration resulted in several potent compounds against CGRP-R with low susceptibility to P-gp mediated efflux. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.027

文献信息

• (E)-Alkenes as replacements of amide bonds: Development of novel and potent acyclic CGRP receptor antagonists
  作者：June J. Kim、Michael R. Wood、Shawn J. Stachel、Pablo de Leon、Ashley Nomland、Craig A. Stump、Melody A. McWherter、Kathy M. Schirripa、Eric L. Moore、Christopher A. Salvatore、Harold G. Selnick

  DOI：10.1016/j.bmcl.2013.11.027

  日期：2014.1

  A new class of CGRP receptor antagonists was identified by replacing the central amide of a previously identified anilide lead structure with ethylene, ethane, or ethyne linkers. (E)-Alkenes as well as alkynes were found to preserve the proper bioactive conformation of the amides, necessary for efficient receptor binding. Further exploration resulted in several potent compounds against CGRP-R with low susceptibility to P-gp mediated efflux. (C) 2013 Elsevier Ltd. All rights reserved.