2-<(2-amino-3-methylbenzyl)thio>-1H-benzimidazole | 106746-65-0

• 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: 2-<(2-amino-3-methylbenzyl)thio>-1H-benzimidazole
• 英文别名: 2-[(1H-Benzimidazol-2-yl)thiomethyl]-6-methylbenzenamine；2-(1H-benzimidazol-2-ylsulfanylmethyl)-6-methylaniline
• CAS: 106746-65-0
• 化学式: C₁₅H₁₅N₃S
• 分子量: 269.37
• InChiKey: OYQQFNJCPSCRGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(2-amino-3-methylbenzyl)thio>-1H-benzimidazole 在 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 以66.2%的产率得到2-[(1H-benzimidazol-2-ylsulfinyl)methyl]-6-methylbenzenamine
  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：

  2-(氯甲基)-6-甲基苯胺盐酸盐 生成 2-<(2-amino-3-methylbenzyl)thio>-1H-benzimidazole
  参考文献：
  名称：

  Method of using (H.sup.+ /K.sup.+)ATPase inhibitors as antiviral agents

  摘要：

  一类(H.sup.+ /K.sup.+)ATP酶抑制剂化合物可用于治疗病毒感染。特别感兴趣的化合物由Formula III定义：其中D为N或CH；其中R.sup.7为从氢化物、烷氧基、氨基、氰基、硝基、羟基、烷基、卤素、卤代烷基、羧基、烷酰基、硝基、氨基、烷基氨基、氨基甲酰基、氨基磺酰基、烷基氨基甲酰基、烷基羰基氨基、烷氧羰基、烷基氨基磺酰基、烷基磺酰胺基、烷硫基、烷砜基和烷磺酰中选择的一个或多个基团；其中R.sup.8选择自氢、烷基和环烷基；其中R.sup.9为从氢化物、烷氧基、氨基、烷基、卤素、氰基、硝基、羟基、卤代烷基、硝基、羧基、烷酰基、氨基、烷基氨基、二烷基氨基、氨基甲酰基、烷基氨基甲酰基、烷基羰基氨基、氨基磺酰基、烷基氨基磺酰基、烷基磺酰胺基、烷氧羰基、烷硫基、烷砜基和烷磺酰中选择的一个或多个基团；其中R.sup.10和R.sup.11分别选择自氢、烷基、芳基、烷基羰基和芳基羰基，其中芳环可能进一步取代一个或多个从烷基、卤素、肼基甲酰基、氨基甲酰基和烷氧基中选择的基团；或其中R.sup.10和R.sup.11与氮原子一起形成一个杂环环。

  公开号：

  US05945425A1

文献信息

• Method of using (H+/K+) ATPase inhibitors as antiviral agents
  申请人：——

  公开号：US20010047038A1

  公开（公告）日：2001-11-29

  A class of compounds which are (H + /K + )ATPase inhibitors can be used for the treatment of viral infections. Compounds of particular interest are defined by Formula III: 1 wherein D is N or CH; wherein R 7 is one or more radicals selected from hydrido, alkoxy, amino, cyano, nitro, hydroxyl, alkyl, halo, haloalkyl, carboxyl, alkanoyl, nitro, amino, alkylamino, amide, alkylamide, alkoxycarbonyl, alkylthio, alkylsulfinyl and alkylsulfonyl; wherein R 9 is one or more radicals selected from hydrido, alkoxy, amino, alkyl, halo, cyano, nitro, hydroxyl, haloalkyl, carboxyl, alkanoyl, nitro, amine, alkylamine, dialkylamine, amide, alkylamide, alkoxycarbonyl, alkylthio, alkylsulfinyl and alkylsulfonyl; and wherein R 10 and R 11 are independently selected from hydrido and alkyl; or a pharmaceutically acceptable salt thereof.

  一类(H+/K+)ATP酶抑制剂类化合物可用于治疗病毒感染。特别感兴趣的化合物由公式III:1定义，其中D为N或CH; R7为一个或多个基团，选自氢，烷氧基，氨基，氰基，硝基，羟基，烷基，卤素基，卤代烷基，羧基，烷酰基，硝基，氨基，烷基氨基，酰胺，烷基酰胺，烷氧羰基，烷基硫醇基，烷基亚砜基和烷基磺酰基; R9为一个或多个基团，选自氢，烷氧基，氨基，烷基，卤素基，氰基，硝基，羟基，卤代烷基，羧基，烷酰基，硝基，胺基，烷基胺基，二烷基胺基，酰胺，烷基酰胺，烷氧羰基，烷基硫醇基，烷基亚砜基和烷基磺酰基; R10和R11独立选择自氢和烷基; 或其药学上可接受的盐。
• Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase
  作者：Gilbert W. Adelstein、Chung H. Yen、Richard A. Haack、Stella Yu、Gary Gullikson、Doreen V. Price、Charles Anglin、Dennis L. Decktor、Henry Tsai、Robert H. Keith

  DOI：10.1021/jm00401a024

  日期：1988.6

  A series of substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase. Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs. Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unsubstituted analogue. The potency showed a correlation to the calculated pKa of the aniline nitrogen atom. Substitutions on the aniline and benzimidazole rings did not further enhance potency. Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system. The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring. One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.
• ADELSTEIN, GILBERT W.;YEN, CHUNG H.;HAACK, RICHARD A.;YU, STELLA;GULLIKSO+, J. MED. CHEM., 31,(1988) N 6, 1215-1220
  作者：ADELSTEIN, GILBERT W.、YEN, CHUNG H.、HAACK, RICHARD A.、YU, STELLA、GULLIKSO+

  DOI：——

  日期：——
• LANG, HANS-JOCHEN;RACKUR, GERHARD;ROSNER, MANFRED;HERLING, ANDREAS W.
  作者：LANG, HANS-JOCHEN、RACKUR, GERHARD、ROSNER, MANFRED、HERLING, ANDREAS W.

  DOI：——

  日期：——
• ——
  作者：LANG H. -J.、 RACKUR G.、 ROSNER M.、 HERLING A.

  DOI：——

  日期：——