2-(1H-Benzimidazol-2-yl sulphinyl)-N,N-dimethyl benzenamine | 112951-55-0

• 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-(1H-Benzimidazol-2-yl sulphinyl)-N,N-dimethyl benzenamine
• 英文别名: 2-(1H-benzimidazol-2-ylsulfinyl)-N,N-dimethylaniline
• CAS: 112951-55-0
• 化学式: C₁₅H₁₅N₃OS
• 分子量: 285.37
• InChiKey: JHYQSLOZFPYZRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 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：
  68.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-dimethylaminothiophenol 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-(1H-Benzimidazol-2-yl sulphinyl)-N,N-dimethyl benzenamine
  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

文献信息

• Certain 2-pyridinyl-phenylsulfinyl-benzoxazoles, the corresponding
  申请人：Fisons plc

  公开号：US04851419A1

  公开（公告）日：1989-07-25

  There are described compounds of formula I, ##STR1## in which A is a benzene or heterocyclic ring, y is 0 or 1, L is a group containing 1 or 2 carbon atoms, or is a single bond, R.sub.9 and R.sub.10 have a variety of significances, e.g. R.sub.10 may form part of a double bond with L, or the group --NR.sub.9 R.sub.10 forms a ring carrying substituents R.sub.1 and R.sub.8, or when L is a single bond --NR.sub.10 and R.sub.8 may form a ring carrying substituents R.sub.16 to R.sub.25, or the group --LNR.sub.9 R.sub.10 forms a heterocyclic ring carrying substituents R.sub.26 to R.sub.33, R.sub.1 to R.sub.8 and R.sub.16 to R.sub.33 have a variety of significances n is 0, 1 or 2, x is 3, 4 or 5, X is S, O or NR.sub.15, R.sub.15 is hydrogen, --COR, --COOR or alkyl optionally substituted by --OCOR, and certain provisos. Processes for making the compounds and pharmaceutical formulations containing them, e.g. for the treatment of conditions involving excess gastric acid secretion, are also described.

  本文描述了化合物I的公式，其中A是苯或杂环环，y为0或1，L是含有1或2个碳原子的基团，或者是一个单键，R.sub.9和R.sub.10具有各种意义，例如R.sub.10可以与L形成双键，或者--NR.sub.9 R.sub.10基团形成一个带有R.sub.1和R.sub.8取代基的环，当L是一个单键时，--NR.sub.10和R.sub.8可以形成一个带有R.sub.16到R.sub.25的取代基的环，或者--LNR.sub.9 R.sub.10基团形成一个带有R.sub.26到R.sub.33的取代基的杂环环，R.sub.1到R.sub.8和R.sub.16到R.sub.33具有各种意义，n为0、1或2，x为3、4或5，X为S、O或NR.sub.15，R.sub.15为氢、--COR、--COOR或烷基，可以选择地被--OCOR取代，以及某些条件。还描述了制备这些化合物和含有它们的制药配方，例如用于治疗涉及过多胃酸分泌的疾病。
• 2-Pyridinyl-phenyl-sulphinyl-and-phenyl-thio-benzimidazoles having
  申请人：Fisons plc

  公开号：US04900751A1

  公开（公告）日：1990-02-13

  Compounds of formula I, ##STR1## in which A is a 5 or 6 membered, fully unsaturated, carbocyclic or heterocyclic ring, B is a 5 or 6 membered, fully unsaturated, nitrogen containing heterocyclic ring, X is NR.sub.19, O or S, R.sub.19 is hydrogen or alkyl optionally substituted by --OCOR, n is 0 or 1, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 have various significances, R.sub.1 and R.sub.2, are hydrogen or alkyl or together with the ring carbon atoms to which they are attached, form a benzene or pyridine ring, which ring carries substituents R.sub.15, R.sub.16, R.sub.17 and R.sub.18, R.sub.15, R.sub.16, R.sub.17 and R.sub.18, have various significances, with certain provisos are described. Processes for making the compounds and pharmaceutical formulations containing them, e.g. for the treatment of conditions including excess gastric acid secretion, are also described.

  化合物的式子为I，其中A是一个5或6成员的，完全不饱和的，碳环或杂环，B是一个5或6成员的，完全不饱和的，含氮的杂环，X是NR.sub.19，O或S，R.sub.19是氢或烷基，可以被-OCOR取代，n为0或1，R.sub.3，R.sub.4，R.sub.5，R.sub.6，R.sub.7，R.sub.8，R.sub.9和R.sub.10具有不同的意义，R.sub.1和R.sub.2是氢或烷基，或与它们附着的环碳原子一起形成苯环或吡啶环，该环携带取代基R.sub.15，R.sub.16，R.sub.17和R.sub.18，R.sub.15，R.sub.16，R.sub.17和R.sub.18具有不同的意义，在某些条件下进行描述。还描述了制备该化合物和含有它们的制药配方，例如用于治疗包括胃酸过多在内的疾病。
• Benzimidazoles, benzoxazoles, benzothiazoles and their production, formulation and use as gastric acid secretion inhibitors
  申请人：FISONS plc

  公开号：EP0220053A2

  公开（公告）日：1987-04-29

  There are described compounds of formula I. in which A is a benzene or heterocyclic ring, y is 0 or 1, L is a group containing 1 or 2 carbon atoms, or is a single bond, R9 and R10 have a variety of significances, eg R10 may form part of a double bond with L, or the group -NR9R10 forms a ring carrying substituents R1 to R8. or when L is a single bond -NR10 and Re may form a ring carrying substituents R16 to R25, or the group -LNR9R10 forms a heterocyclic ring carrying substituents R26 to R33, R1 to R8 and R16 to R33 have a variety of significances n is 0, 1 or 2, x is 3, 4 or 5, X is S, O or NR15, R15 is hydrogen, -COR, -COOR or alkyl optionally substituted by -OCOR, and certain provisos. Processes for making the compounds and pharmaceutical formulations containing them, eg for the treatment of conditions involving excess gastric acid secretion, are also described.

  所述化合物为式 I。 其中 A 是苯环或杂环、 y 是 0 或 1、 L 是含有 1 或 2 个碳原子的基团，或者是单键、 R9 和 R10 有多种含义，例如 R10 可与 L 形成双键的一部分，或 基团 -NR9R10 形成一个带有取代基 R1 至 R8 的环。 或 当 L 是单键时，-NR10 和 Re 可形成一个带有取代基 R16 至 R25 的环，或 基团 -LNR9R10 形成一个杂环，带有取代基 R26 至 R33、 R1 至 R8 和 R16 至 R33 有多种含义 n 是 0、1 或 2、 x 是 3、4 或 5、 X 是 S、O 或 NR15、 R15 是氢、-COR、-COR 或任选被-OCOR.取代的烷基、 以及某些但书。 此外，还描述了制造这些化合物和含有这些化合物的药物制剂的工艺，例如用于治疗胃酸分泌过多的病症。
• US4851419A
  申请人：——

  公开号：US4851419A

  公开（公告）日：1989-07-25
• US4900751A
  申请人：——

  公开号：US4900751A

  公开（公告）日：1990-02-13