5-phenyl-N-[(1S)-1-phenylpropyl]-1H-imidazo[4,5-b]pyridine-7-carboxamide | 244090-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-phenyl-N-[(1S)-1-phenylpropyl]-1H-imidazo[4,5-b]pyridine-7-carboxamide
• CAS: 244090-23-1
• 化学式: C₂₂H₂₀N₄O
• 分子量: 356.427
• InChiKey: FJABACJGDMNFHR-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-phenyl-N-[(1S)-1-phenylpropyl]-1H-imidazo[4,5-b]pyridine-7-carboxamide 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以78%的产率得到3-methyl-5-phenyl-3H-imidazo[4,5-b]pyridine-7-carboxylic acid (1-phenyl-propyl)-amide
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9
• 作为产物：
  描述：

  Ethyl 5-phenyl-3H-imidazo[4,5-b]pyridine-7-carboxylate 在 盐酸 、 水 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 14.0h， 生成 5-phenyl-N-[(1S)-1-phenylpropyl]-1H-imidazo[4,5-b]pyridine-7-carboxamide
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9

文献信息

• Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists
  作者：G.A.M Giardina、M Artico、S Cavagnera、A Cerri、E Consolandi、S Gagliardi、D Graziani、M Grugni、D.W.P Hay、M.A Luttmann、R Mena、L.F Raveglia、R Rigolio、H.M Sarau、D.B Schmidt、G Zanoni、C Farina

  DOI：10.1016/s0014-827x(99)00043-9

  日期：1999.6

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.