5-trifluoromethyl-2-methylsulfinyl-benzimidazole | 86604-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-trifluoromethyl-2-methylsulfinyl-benzimidazole
• 英文别名: 2-methylsulfinyl-6-(trifluoromethyl)-1H-benzimidazole
• CAS: 86604-84-4
• 化学式: C₉H₇F₃N₂OS
• 分子量: 248.229
• InChiKey: XYEZDKXWPJBOKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-trifluoromethyl-2-methylsulfinyl-benzimidazole 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 1.5h， 生成 2-(5-Trifluoromethyl-1H-benzoimidazole-2-sulfinyl)-phenylamine
  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：

  间氯过氧苯甲酸 、 5-trifluoromethyl-2-methylthio-benzimidazole 在 potassium carbonate 、 乙腈 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以1.8 g of 5-trifluoromethyl-2-methylsulfinyl-benzimidazole of m.p. 135° C. are obtained的产率得到5-trifluoromethyl-2-methylsulfinyl-benzimidazole
  参考文献：
  名称：

  2-Pyridylmethyl thio(sulfinyl)benzimidazoles with gastric acid secretion

  摘要：

  4-或5-三氟甲基-2-[(4-甲氧基-2-吡啶甲基)硫基或亚砜基]-（-苯并咪唑可作为药物组合物的成分，用于保护暖血动物的胃和肠道，并抑制其胃酸分泌。

  公开号：

  US04472409A1

文献信息

• Substituierte Benzimidazole, Verfahren zu ihrer Herstellung, ihre Anwendung und sie enthaltende Arzneimittel
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：EP0080602A1

  公开（公告）日：1983-06-08

  Substituierte Benzimidazole der allgemeinen Formel I worin R' Wasserstoff oder Methyl, R2 Wasserstoff oder Methyl und n 0 oder 1 bedeutet und ihre Salze sind neue Verbindungen, die die Magensäuresekretion hemmen und die eine ausgezeichnete Magen- und Darmschutzwirkung bei Warmblütern zeigen.

  通式 I 的取代苯并咪唑（其中 R' 为氢或甲基，R2 为氢或甲基，n 为 0 或 1）及其盐类是新型化合物，可抑制胃酸分泌，对温血动物的胃肠道具有极佳的保护活性。
• US4472409A
  申请人：——

  公开号：US4472409A

  公开（公告）日：1984-09-18
• Amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole as acid-stable prodrugs of potential inhibitors of H+K+ ATPase
  作者：K Hirai、H Koike、T Ishiba、S Ueda、I Makino、H Yamada、T Ichihashi、Y Mizushima、M Ishikawa、Y Ishihara、Y Hara、H Hirose、N Shima、M Doteuchi

  DOI：10.1016/0223-5234(91)90024-h

  日期：1991.3

  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.
• 2-Pyridylmethyl thio(sulfinyl)benzimidazoles with gastric acid secretion
  申请人：Byk Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung

  公开号：US04472409A1

  公开（公告）日：1984-09-18

  4- or 5-Trifluoromethyl-2-[(4-methoxy-2-pyridylmethyl)thio or sulfinyl]-(-benzimidazoles are useful as such or in medicament compositions for protecting the stomach and intestines and for inhibiting gastric acid secretion of warm-blooded animals to which they are administered.

  4-或5-三氟甲基-2-[(4-甲氧基-2-吡啶甲基)硫基或亚砜基]-(-苯并咪唑可用于保护其所施用的温血动物的胃和肠道，并抑制胃酸分泌，或用于药物组合物中。