N-(tert-butoxycarbonylmethyl)-2-[4-(N-Cbz-piperidino)carbonyl]-N-{N'[m-(2-propenyloxycarbonyl)phenyl]uridomethylcarbamoyl}aniline | 171724-73-5

• 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: N-(tert-butoxycarbonylmethyl)-2-[4-(N-Cbz-piperidino)carbonyl]-N-{N'[m-(2-propenyloxycarbonyl)phenyl]uridomethylcarbamoyl}aniline
• CAS: 171724-73-5
• 化学式: C₃₉H₄₄N₄O₉
• 分子量: 712.8
• InChiKey: BPDHXPGJULEWBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  160.65
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonylmethyl)-2-[4-(N-Cbz-piperidino)carbonyl]-N-{N'[m-(2-propenyloxycarbonyl)phenyl]uridomethylcarbamoyl}aniline 在 palladium on activated charcoal 四氢吡咯 、 四(三苯基膦)钯 、 三苯基膦 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-(tert-butoxycarbonylmethyl)-2-[4-(piperidino)carbonyl]-N-[N'(m-carboxylphenyl)uridomethylcarbamoyl]aniline
  参考文献：
  名称：

  Synthesis and pharmacological properties of ureidomethylcarbamoylphenylketone derivatives. A new potent and subtype-selective nonpeptide CCK-B/gastrin receptor antagonist, S-0509

  摘要：

  A novel series of CCK-B/gastrin receptor antagonists-ureidomethylcarbamoylphenylketone derivatives were designed, synthesized, and evaluated for activity. Structure-activity relationship studies revealed the importance of a carboxylic acid at substituent R-2 and a tert-butoxycarbonyl group at R-1 in structure A. Compound 7a (S-0509) showed remarkable affinity for the CCK-B/gastrin receptor and a subtype selectivity profile in vitro. Administration (id) of 7a led to excellent inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats with an ED50 value of 0.014 mg/kg. Furthermore, 7a proved to have poor blood-brain permeability by its small effect on enhancement of morphine analgesia. Thus, S-0509 has an increase in selectivity for the peripheral effects of gastrin antagonism from the central effects of CCK-B antagonism. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00104-1
• 作为产物：
  描述：

  2-(N'-CBz-piperidine-4-carbonyl)aniline 在 四丁基溴化铵 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(tert-butoxycarbonylmethyl)-2-[4-(N-Cbz-piperidino)carbonyl]-N-{N'[m-(2-propenyloxycarbonyl)phenyl]uridomethylcarbamoyl}aniline
  参考文献：
  名称：

  Synthesis and pharmacological properties of ureidomethylcarbamoylphenylketone derivatives. A new potent and subtype-selective nonpeptide CCK-B/gastrin receptor antagonist, S-0509

  摘要：

  A novel series of CCK-B/gastrin receptor antagonists-ureidomethylcarbamoylphenylketone derivatives were designed, synthesized, and evaluated for activity. Structure-activity relationship studies revealed the importance of a carboxylic acid at substituent R-2 and a tert-butoxycarbonyl group at R-1 in structure A. Compound 7a (S-0509) showed remarkable affinity for the CCK-B/gastrin receptor and a subtype selectivity profile in vitro. Administration (id) of 7a led to excellent inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats with an ED50 value of 0.014 mg/kg. Furthermore, 7a proved to have poor blood-brain permeability by its small effect on enhancement of morphine analgesia. Thus, S-0509 has an increase in selectivity for the peripheral effects of gastrin antagonism from the central effects of CCK-B antagonism. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00104-1