[benzyloxycarbonylaminoacetyl-(3-methoxyphenyl)amino]acetic acid tert-butyl ester | 195711-94-5

• 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: [benzyloxycarbonylaminoacetyl-(3-methoxyphenyl)amino]acetic acid tert-butyl ester
• CAS: 195711-94-5
• 化学式: C₂₃H₂₈N₂O₆
• 分子量: 428.485
• InChiKey: QHBLZIAFFUHQFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [benzyloxycarbonylaminoacetyl-(3-methoxyphenyl)amino]acetic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 1-羟基苯并三唑 、 苯甲醚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 66.0h， 生成 {3-[3-(3-piperidin-1-ylmethylphenoxy)propylcarbamoyl]propyl}carbamic acid 3-(3-{[(3-methoxyphenyl)-(2-morpholin-4-yl-2-oxoethyl)carbamoyl]methyl}ureido)benzyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of dual histamine H2 and gastrin receptor antagonists with noncyclic gastrin receptor antagonistic moieties

  摘要：

  In order to study structure-activity relationships of dual histamine H-2 and gastrin receptor antagonists as well as to improve their low oral absorbability, their prototype benzodiazepine gastrin receptor antagonistic moieties were altered to a conformationally flexible noncyclic dipeptide equivalent. This skeletal modification significantly potentiated the binding affinity of hybrid compounds for the histamine H-2 receptor, whereas their affinity for the gastrin receptor and receptor selectivity over the CCK-A receptor varied widely with the substituents on the gastrin moiety. Among them, {3-[3-(3-piperidin-1-ylmethylphenoxy)-propylcarbamoyl]propyl}carbamic acid 3-[3-({(3-methoxyphenyl)[(methylphenylcarbamoyl)methyl]carbamoyl}methyl)ureido]-benzyl ester (7a) showed the highest dual histamine H-2 and gastrin receptor antagonistic activities. It also displayed distinct gastric acid antisecretory activity in vivo for two assays, namely, Schild's rat method by id administration and the rat pylorus ligation method by oral administration. With the latter case, dose-response relationships were observed for the first time, suggesting its substantially improved oral absorbability. However, 7a did not display distinct in vivo gastric acid antisecretory activity for the assay with Heidenhain pouch dogs. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00076-x
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.58h， 生成 [benzyloxycarbonylaminoacetyl-(3-methoxyphenyl)amino]acetic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of dual histamine H2 and gastrin receptor antagonists with noncyclic gastrin receptor antagonistic moieties

  摘要：

  In order to study structure-activity relationships of dual histamine H-2 and gastrin receptor antagonists as well as to improve their low oral absorbability, their prototype benzodiazepine gastrin receptor antagonistic moieties were altered to a conformationally flexible noncyclic dipeptide equivalent. This skeletal modification significantly potentiated the binding affinity of hybrid compounds for the histamine H-2 receptor, whereas their affinity for the gastrin receptor and receptor selectivity over the CCK-A receptor varied widely with the substituents on the gastrin moiety. Among them, {3-[3-(3-piperidin-1-ylmethylphenoxy)-propylcarbamoyl]propyl}carbamic acid 3-[3-({(3-methoxyphenyl)[(methylphenylcarbamoyl)methyl]carbamoyl}methyl)ureido]-benzyl ester (7a) showed the highest dual histamine H-2 and gastrin receptor antagonistic activities. It also displayed distinct gastric acid antisecretory activity in vivo for two assays, namely, Schild's rat method by id administration and the rat pylorus ligation method by oral administration. With the latter case, dose-response relationships were observed for the first time, suggesting its substantially improved oral absorbability. However, 7a did not display distinct in vivo gastric acid antisecretory activity for the assay with Heidenhain pouch dogs. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00076-x