(S)-2-Amino-N-[2-(1H-benzoimidazol-2-ylsulfanylmethyl)-phenyl]-3-phenyl-propionamide | 111881-45-9

• 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)-2-Amino-N-[2-(1H-benzoimidazol-2-ylsulfanylmethyl)-phenyl]-3-phenyl-propionamide
• 英文别名: (2S)-2-amino-N-[2-(1H-benzimidazol-2-ylsulfanylmethyl)phenyl]-3-phenylpropanamide
• CAS: 111881-45-9
• 化学式: C₂₃H₂₂N₄OS
• 分子量: 402.52
• InChiKey: FAUBFROKOCMATM-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-N-[2-(1H-benzoimidazol-2-ylsulfanylmethyl)-phenyl]-3-phenyl-propionamide 在 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以38.8%的产率得到(S)-2-Amino-N-[2-(1H-benzoimidazole-2-sulfinylmethyl)-phenyl]-3-phenyl-propionamide
  参考文献：
  名称：

  Amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole as acid-stable prodrugs of potential inhibitors of H+K+ ATPase

  摘要：

  A series of amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole were prepared and found to possess gastric antisecretory activity on oral administration. (Glycylaminobenzyl)sulfinyl compound 23a, stable in artificial gastric juice (pH 1.2), was given orally to dogs. It was absorbed efficiently and converted into aniline derivative 7a which showed a very high plasma concentration. Compound 23a was hydrolyzed by the action of aminopeptidase present in plasma or the brush border fraction of the small intestine to release the terminal glycine. omicron-Aniline derivatives showed good activity in in vitro H+/K+-ATPase inhibition as well as in the inhibition of histamine stimulated acid secretion in isolated bullfrog gastric mucosa. Although these omicron-aniline derivatives showed no or weak gastric antisecretory activity in rat by id administration, they were active when administered ip. Therefore, these amino acid amides were considered to be acid stable prodrugs of proton pump inhibiting omicron-aniline derivatives. The mechanism of H+/K+-ATPase inhibition of 7a was also examined.

  DOI：

  10.1016/0223-5234(91)90024-h
• 作为产物：
  描述：

  N-benzyloxycarbonyl-L-phenylalanyl chloride 在 sodium hydroxide 、 氯化亚砜 、 氢溴酸 、 溶剂黄146 作用下， 以 六甲基磷酰三胺 、 乙醇 、 水 、 乙腈 、 苯 为溶剂， 反应 8.83h， 生成 (S)-2-Amino-N-[2-(1H-benzoimidazol-2-ylsulfanylmethyl)-phenyl]-3-phenyl-propionamide
  参考文献：
  名称：

  Amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole as acid-stable prodrugs of potential inhibitors of H+K+ ATPase

  摘要：

  A series of amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole were prepared and found to possess gastric antisecretory activity on oral administration. (Glycylaminobenzyl)sulfinyl compound 23a, stable in artificial gastric juice (pH 1.2), was given orally to dogs. It was absorbed efficiently and converted into aniline derivative 7a which showed a very high plasma concentration. Compound 23a was hydrolyzed by the action of aminopeptidase present in plasma or the brush border fraction of the small intestine to release the terminal glycine. omicron-Aniline derivatives showed good activity in in vitro H+/K+-ATPase inhibition as well as in the inhibition of histamine stimulated acid secretion in isolated bullfrog gastric mucosa. Although these omicron-aniline derivatives showed no or weak gastric antisecretory activity in rat by id administration, they were active when administered ip. Therefore, these amino acid amides were considered to be acid stable prodrugs of proton pump inhibiting omicron-aniline derivatives. The mechanism of H+/K+-ATPase inhibition of 7a was also examined.

  DOI：

  10.1016/0223-5234(91)90024-h