(S)-4-{3-[3-(5-tert-butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl)ureido]benzyloxycarbonylamino}butyric acid methyl ester | 195621-81-9

• 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: (S)-4-{3-[3-(5-tert-butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl)ureido]benzyloxycarbonylamino}butyric acid methyl ester
• CAS: 195621-81-9
• 化学式: C₂₉H₃₆N₄O₈S
• 分子量: 600.693
• InChiKey: CESYLPYVSOWZSZ-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  152.37
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-4-{3-[3-(5-tert-butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl)ureido]benzyloxycarbonylamino}butyric acid methyl ester 在 氢氧化钾 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (+)-(S)-{4-oxo-[3-(3-{3-[(3-piperidin-1-ylmethylphenoxy)propylcarbamoyl]propyl}carbamoyloxymethyl)phenyl]ureido}-3,4-dihydro-2H-(1,5-benzothiazepin-5-yl)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 modified benzodiazepine skeletons

  摘要：

  Three different types of dual histamine H-2 and gastrin receptor antagonists, e.g. those bearing a benzazepine, benzoxazepine, or benzothiazepine skeleton instead of the benzodiazepine one as a gastrin receptor antagonistic moiety were synthesized to reduce high hydrophobicity of parent compounds and evaluated for the dual activities. These skeletal modifications significantly potentiated the binding affinity of dual antagonists with histamine H-2, receptor but markedly diminished their binding affinity with the gastrin receptor and the gastrin versus CCK-A receptor selectivity. We evaluated in vivo gastric acid antisecretory activities for some representative compounds by the rat pylorus ligation method for 10 mg kg(-1) dose by oral route. However, they exerted only low inhibitory activities for oral dose with % inhibition values ranging between 32 and 53%. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00075-8
• 作为产物：
  描述：

  amino-(2-nitrophenylsulfanyl)acetic acid 在 palladium on activated charcoal 氢氧化钾 、 Diethy phosphocyanidate 、 四丁基溴化铵 、 氢气 、 sodium carbonate 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-4-{3-[3-(5-tert-butoxycarbonylmethyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl)ureido]benzyloxycarbonylamino}butyric acid methyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of dual histamine H2 and gastrin receptor antagonists with modified benzodiazepine skeletons

  摘要：

  Three different types of dual histamine H-2 and gastrin receptor antagonists, e.g. those bearing a benzazepine, benzoxazepine, or benzothiazepine skeleton instead of the benzodiazepine one as a gastrin receptor antagonistic moiety were synthesized to reduce high hydrophobicity of parent compounds and evaluated for the dual activities. These skeletal modifications significantly potentiated the binding affinity of dual antagonists with histamine H-2, receptor but markedly diminished their binding affinity with the gastrin receptor and the gastrin versus CCK-A receptor selectivity. We evaluated in vivo gastric acid antisecretory activities for some representative compounds by the rat pylorus ligation method for 10 mg kg(-1) dose by oral route. However, they exerted only low inhibitory activities for oral dose with % inhibition values ranging between 32 and 53%. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00075-8