2-[(1H-Benzimidazol-2-yl)thiomethyl]-N,N-dimethylbenzenamine | 104340-38-7

• 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-[(1H-Benzimidazol-2-yl)thiomethyl]-N,N-dimethylbenzenamine
• 英文别名: 2-<(1H-benzimidazol-2-ylthio)methyl>-N,N-dimethylaniline；2-(2-dimethylaminobenzylthio)benzimidazole；2-[(1H-benzimidazol-2-ylthio)methyl]-N,N-dimethylbenzenamine；2-[(1H-benzimidazol-2-ylthio)methyl]-N,N-dimethylaniline；Benzenamine, 2-[(1H-benzimidazol-2-ylthio)methyl]-N,N-dimethyl-；2-(1H-benzimidazol-2-ylsulfanylmethyl)-N,N-dimethylaniline
• CAS: 104340-38-7
• 化学式: C₁₆H₁₇N₃S
• 分子量: 283.397
• InChiKey: BLKLDWQFHUIMPR-UHFFFAOYSA-N

物化性质

• 熔点：
  167-170 °C(Solv: isopropanol (67-63-0))
• 沸点：
  490.8±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(1H-Benzimidazol-2-yl)thiomethyl]-N,N-dimethylbenzenamine 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以53%的产率得到2-((2-二甲基氨基苄基)亚磺酰)苯并咪唑
  参考文献：
  名称：

  Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase

  摘要：

  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.

  DOI：

  10.1021/jm00401a024
• 作为产物：
  描述：

  1H-苯并咪唑-2-硫醇 生成 2-[(1H-Benzimidazol-2-yl)thiomethyl]-N,N-dimethylbenzenamine
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Method of using (H.sup.+ /K.sup.+)ATPase inhibitors as antiviral agents
  申请人：G.D. Searle & Co.

  公开号：US05945425A1

  公开（公告）日：1999-08-31

  A class of compounds which are (H.sup.+ /K.sup.+)ATPase inhibitors can be used for the treatment of viral infections. Compounds of particular interest are defined by Formula III: ##STR1## wherein D is N or CH; wherein R.sup.7 is one or more radicals selected from hydrido, alkoxy, amino, cyano, nitro, hydroxyl, alkyl, halo, haloalkyl, carboxyl, alkanoyl, nitro, amino, alkylamino, aminocarbonyl, aminosulfonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylthio, alkylsulfinyl and alkylsulfonyl; wherein R.sup.8 is selected from hydrido, alkyl and cycloalkyl; wherein R.sup.9 is one or more radicals selected from hydrido, alkoxy, amino, alkyl, halo, cyano, nitro, hydroxyl, haloalkyl, nitro, carboxyl, alkanoyl, amino, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, alkylcarbonylamino, aminosulfonyl, alkylaminosulfonyl, alkylsulfonylamino, alkoxycarbonyl, alkylthio, alkylsulfinyl and alkylsulfonyl; and wherein R.sup.10 and R.sup.11 are independently selected from hydrido, alkyl, aryl, alkylcarbonyl and arylcarbonyl wherein the aryl ring may be further substituted with one or more radicals selected from alkyl, halo, hydrazidylcarbonyl, aminocarbonyl and alkoxy; or wherein R.sup.10 and R.sup.11 together with the nitrogen atom form a heterocyclic ring.

  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。
• Method of protecting gastrointestinal tract
  申请人：Nippon Chemiphar Co., Ltd.

  公开号：US04824856A1

  公开（公告）日：1989-04-25

  A method of protecting gastrointestinal tract in a mammal from the untoward, non-gastric-acid-induced effects of exposure to gastrointestinally injuruous agents, which comprises administering orally to said mammal a non-antisecretory amount of a benzimidazole derivative having the formula (I): ##STR1## wherein R.sup.1 is the hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group, phenyl group or aralkyl group, R.sup.2 is the hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 together with the adjacent nitrogen atom forms a ring, and each of R.sup.3 and R.sup.4 independently is the hydrogen atom, a halogen atom, the trifluoromethyl group, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group or an amino group.

  一种保护哺乳动物胃肠道免受胃酸以外的有害影响的方法，包括口服给予一种苯并咪唑衍生物，其化学式为(I)：##STR1## 其中R.sup.1是氢原子、具有1到8个碳原子的烷基、环烷基、苯基或芳基烷基，R.sup.2是氢原子或较低的烷基，或者R.sup.1和R.sup.2与相邻的氮原子一起形成一个环，R.sup.3和R.sup.4中的每一个独立地是氢原子、卤素原子、三氟甲基基团、较低的烷基、较低的烷氧基、较低的烷氧羰基或氨基。
• 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。
• Stabilized benzimidazole derivative and composition
  申请人：Nippon Chemiphar Co., Ltd.

  公开号：US05294439A1

  公开（公告）日：1994-03-15

  A stabilized physiologically active benzimidazole derivative having the formula (I): ##STR1## wherein R.sup.1 is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a fluoroalkyl group having 1 to 6 carbon atoms, a cycloalkyl group, phenyl group or an aralkyl group, R.sup.2 is hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 together with the adjacent nitrogen atom form a ring, and each of R.sup.3a, R.sup.3b, R.sup.4a, R.sup.4b and R.sup.4c independently is hydrogen atom, a halogen atom, a fluoroalkyl group having 1 to 6 carbon atoms, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group or an amino group. The stabilized benzimidazole derivative is in amorphous form or present in contact with a basic material.

  具有以下公式（I）的稳定的生理活性苯并咪唑衍生物：##STR1## 其中，R1是氢原子，具有1至8个碳原子的烷基，具有1至6个碳原子的氟烷基，环烷基，苯基或芳基烷基，R2是氢原子或较低的烷基，或R1和R2与相邻的氮原子一起形成环，且R3a，R3b，R4a，R4b和R4c中的每一个独立地是氢原子，卤原子，具有1至6个碳原子的氟烷基，较低的烷基，较低的烷氧基，较低的烷氧羰基或氨基。稳定的苯并咪唑衍生物以非晶态形式存在或与碱性物质接触。
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