benzyl 4-[(2S)-3-[[(2S)-1-[(2S)-1-amino-1-oxohexan-2-yl]oxy-4-methylpentan-2-yl]amino]-3-oxo-2-(phenylmethoxycarbonylamino)propyl]imidazole-1-carboxylate | 200949-67-3

• 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: benzyl 4-[(2S)-3-[[(2S)-1-[(2S)-1-amino-1-oxohexan-2-yl]oxy-4-methylpentan-2-yl]amino]-3-oxo-2-(phenylmethoxycarbonylamino)propyl]imidazole-1-carboxylate
• CAS: 200949-67-3
• 化学式: C₃₄H₄₅N₅O₇
• 分子量: 635.761
• InChiKey: CJLSBNVNMBASOB-DTXPUJKBSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 4-[(2S)-3-[[(2S)-1-[(2S)-1-amino-1-oxohexan-2-yl]oxy-4-methylpentan-2-yl]amino]-3-oxo-2-(phenylmethoxycarbonylamino)propyl]imidazole-1-carboxylate 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Boc-D-Phe-Gln-Trp-Ala-Val-Gly-His-LeuΨ(CH2O)Nle-NH2
  参考文献：
  名称：

  Syntheses and biological activities of bombesin analogs modified in the C-terminal dipeptide part

  摘要：

  Bombesin receptor antagonists are possible therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis on the mechanism of action of gastrin associating an activating enzyme system to the receptor and on the results reported in the litterature, we have synthesized bombesin analogues which have been modified in the C-terminal Leu(13)-Leu(14) amide part. We have shown that modification in the C-terminal part of the bombesin strongly affected the biological activity in rat pancreatic acini. The most potent compound which is described here, H-D-Phe- Gln-Trp-Ala-Val-Gly-His-Leu-psi(CH2)Leu-NH2, was able to recognize the bombesin receptor on rat pancreatic acini (Ki 4.3 nM) and antagonized the bombesin stimulated amylase secretion (Ki 7.7 nM).

  DOI：

  10.1016/s0223-5234(99)80063-4
• 作为产物：
  描述：

  (R)-(+)-2-bromohexanoic acid 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 sodium hydroxide 、 N-羟基丁二酰亚胺 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙腈 为溶剂， 反应 24.0h， 生成 benzyl 4-[(2S)-3-[[(2S)-1-[(2S)-1-amino-1-oxohexan-2-yl]oxy-4-methylpentan-2-yl]amino]-3-oxo-2-(phenylmethoxycarbonylamino)propyl]imidazole-1-carboxylate
  参考文献：
  名称：

  Syntheses and biological activities of bombesin analogs modified in the C-terminal dipeptide part

  摘要：

  Bombesin receptor antagonists are possible therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis on the mechanism of action of gastrin associating an activating enzyme system to the receptor and on the results reported in the litterature, we have synthesized bombesin analogues which have been modified in the C-terminal Leu(13)-Leu(14) amide part. We have shown that modification in the C-terminal part of the bombesin strongly affected the biological activity in rat pancreatic acini. The most potent compound which is described here, H-D-Phe- Gln-Trp-Ala-Val-Gly-His-Leu-psi(CH2)Leu-NH2, was able to recognize the bombesin receptor on rat pancreatic acini (Ki 4.3 nM) and antagonized the bombesin stimulated amylase secretion (Ki 7.7 nM).

  DOI：

  10.1016/s0223-5234(99)80063-4