1-(2-吡啶基甲基)-1,3-二氢-2H-咪唑-2-硫酮 | 106984-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 1-(2-吡啶基甲基)-1,3-二氢-2H-咪唑-2-硫酮
• 英文名称: 1-(2-pyridylmethyl)-1,3-dihydro-2H-imidazole-2-thione
• 英文别名: 1-(pyridin-2-ylmethyl)-1H-imidazole-2-thiol；3-(pyridin-2-ylmethyl)-1H-imidazole-2-thione
• CAS: 106984-85-4
• 化学式: C₉H₉N₃S
• mdl: MFCD11201072
• 分子量: 191.257
• InChiKey: RFUCFMSXWUCZLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-吡啶基甲基)-1,3-二氢-2H-咪唑-2-硫酮 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  2-[（2-氨基苄基）亚磺酰基] -1-（2-吡啶基）-1,4,5,6-四氢环戊[d]咪唑类是一类新型的胃H + / K + -ATPase抑制剂。

  摘要：

  合成了2-亚磺酰咪唑类化合物，并研究了其作为胃H + / K（+）-ATPase的潜在抑制剂。发现4,5-未取代的咪唑系列6-11和1,4,5,6-四氢环戊[d]咪唑系列12是酸分泌酶H + / K（+）-ATPase的有效抑制剂。结构-活性关系表明，在咪唑部分的1位上取代了2-吡啶基，并在2位上结合了（2-氨基苄基）-亚磺酰基，导致了具有良好化学稳定性的高活性化合物。咪唑部分中的其他取代方式导致生物活性降低。选择了2-[（2-氨基苄基）亚磺酰基] -1- [2-（3-甲基吡啶基）]-1,4,5,6-四氢环戊++ ++ ++ [d]-咪唑（12h，T-776）作为潜在的临床候选者进行进一步开发。

  DOI：

  10.1021/jm950610n
• 作为产物：
  描述：

  (2,2-diethoxy-ethyl)-pyridin-2-ylmethylene-amine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 1-(2-吡啶基甲基)-1,3-二氢-2H-咪唑-2-硫酮
  参考文献：
  名称：

  Inhibitors of dopamine .beta.-hydroxylase. 3. Some 1-(pyridylmethyl)imidazole-2-thiones

  摘要：

  The 1-benzylimidazole-2-thione moiety has been previously shown by Kruse et al. to be broadly associated with dopamine beta-hydroxylase (DBH) inhibitory activity both in vitro and in vivo in spontaneously hypertensive rats (SHR). An extension of structure-activity studies to 1-(pyridylmethyl)- and 1-(oxypyridylmethyl)imidazole-2-thiones is reported here in an attempt to exploit the pH differential that exists across the chromaffin vesicle membrane. We hypothesized that the weakly basic pyridyl compounds would diffuse into the acidic vesicles in their neutral forms where protonation and concentration would occur to enhance their in vivo effectiveness as inhibitors. To test this hypothesis, isomeric 2-, 3- and 4-(1-pyridylmethyl)imidazole-2-thiones were synthesized from the appropriate pyridinecarboxaldehydes by reductive alkylation of aminoacetaldehyde dialkyl acetal followed by imidazole-2-thione formation using acidic potassium thiocyanate. Related oxypyridyl compounds were synthesized by first preparing the appropriate aldehyde intermediate followed by conversion to the imidazole-2-thione by the same procedure. The unsubstituted pyridylmethyl compounds showed modest DBH inhibition in vitro but, consistent with a transport-mediated increase in observed potency, showed significant effects in vivo to increase the vascular ratio of dopamine to norepinephrine and to lower blood pressure.

  DOI：

  10.1021/jm00391a008

文献信息

• Pyridyl-substituted imidazoles, compositions containing same and methods
  申请人：Tanabe Seiyaku Company, Ltd.

  公开号：US04996217A1

  公开（公告）日：1991-02-26

  Novel imidazole of the formula: ##STR1## wherein Ring A is pyridyl group or a substituted pyridyl group; Ring B is phenyl group or a substituted phenyl group; R.sup.1 and R.sup.2 are hydrogen atom or are combined together to form a group of the formula: --(CH.sub.2).sub.q --; m is 1 or 2; n is 0, 1 or 2; and q is 3 or 4, or a salt thereof are disclosed. Said derivative (I) and a salt thereof are useful as anti-ulcer agents.

  公开了式子为：##STR1##的新型咪唑衍生物。其中环A是吡啶基或取代的吡啶基；环B是苯基或取代的苯基；R.sup.1和R.sup.2是氢原子或结合在一起形成式子：--(CH.sub.2).sub.q --的基团；m为1或2；n为0、1或2；q为3或4，或其盐。所述衍生物(I)及其盐可作为抗溃疡药物。
• Imidazole derivatives
  申请人：Tanabe Seiyaku Co. Ltd.

  公开号：US05002945A1

  公开（公告）日：1991-03-26

  Novel imidazole of the formula: ##STR1## wherein Ring A is pyridyl group or a substituted pyridyl group; Ring B is phenyl group or a substituted phenyl group; R.sup.1 and R.sup.2 are hydrogen atom or are combined together to form a group of the formula: --(CH.sub.2).sub.q --; m is 1 or 2; n is 0, 1 or 2; and q is 3 or 4, or a salt thereof are disclosed. Said derivative (I) and a salt thereof are useful as anti-ulcer agents.

  公开了一种式子为：##STR1## 的新型咪唑衍生物，其中环A是吡啶基或取代吡啶基；环B是苯基或取代苯基；R.sup.1和R.sup.2是氢原子或结合在一起形成式子：--(CH.sub.2).sub.q --的基团；m为1或2；n为0、1或2；q为3或4；或其盐。所述衍生物(I)及其盐可用作抗溃疡剂。
• Imidazole derivatives and preparation thereof
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05053417A1

  公开（公告）日：1991-10-01

  Novel imidazole of the formula: ##STR1## wherein Ring A is pyridyl group or a substituted pyridyl group; Ring B is phenyl group or a substituted phenyl group; R.sup.1 and R.sup.2 are hydrogen atom or are combined together to form a group of the formula: --(CH.sub.2).sub.q --; m is 1 or 2; n is 0, 1 or 2; and q is 3 or 4, or a salt thereof are disclosed. Said derivative (I) and a salt thereof are useful as anti-ulcer agents.

  公开了一种式子为：##STR1## 的新型咪唑衍生物，其中环A是吡啶基团或取代的吡啶基团；环B是苯基团或取代的苯基团；R.sup.1和R.sup.2是氢原子或结合在一起形成式子为：--(CH.sub.2).sub.q --的基团；m为1或2；n为0、1或2；q为3或4，或其盐。所述衍生物(I)及其盐可用作抗溃疡剂。
• Dopamine-beta-hydroxylase inhibitors
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0214740A2

  公开（公告）日：1987-03-18

  Compounds of structure (I) in which Y is H, OH, halogen or C1-4 alkoxy; X is H, halogen, halo C1-4 alkyl, n is 1 to 5 and R is H or C1-4 alkyl and phar- maceu- tically acceptable salts or hydrates thereof, processes fortheir preparation, compositions containing them and their use in therapy.

  结构(I)的化合物 其中 Y 为 H、OH、卤素或 C1-4 烷氧基；X 为 H、卤素、卤代 C1-4 烷基，n 为 1 至 5，R 为 H 或 C1-4 烷基，以及它们的可接受盐或水合物。 及其可接受的盐或水合物、其制备工艺、含有它们的组合物以及它们在治疗中的用途。
• Imidazole derivatives, processes for the preparation of the same, pharmaceutical compositions comprising the same, the use of the same for the manufacture of medicaments of therapeutic value, and intermediates formed during said processes
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0270091A1

  公开（公告）日：1988-06-08

  Novel imidazole of the formula: wherein Ring A is pyridyl group or a substituted pyridyl group; Ring B is phenyl group or a substituted phenyl group; R1 and R2 are hydrogen atom or are combined together to form a group of the formula: --(CH2 )q-; m is 1 or 2; n is 0, 1 or 2; and q is 3 or 4, or a salt thereof are disclosed. Said derivative (I) and a salt thereof are useful an anti-ulcer agents. Processes for the preparation of such derivatives are also provided, together with chemical intermediates formed during said processes. Pharmaceutical compositions comprising the same are further provided. The use of such compounds is also provided for the manufacture of medicaments of therapeutic value.

  本发明公开了式如下的新型咪唑：其中环 A 是吡啶基或取代的吡啶基；环 B 是苯基或取代的苯基；R1 和 R2 是氢原子或结合在一起形成式如下的基团：--(CH2 )q-；m 是 1 或 2；n 是 0、1 或 2；q 是 3 或 4，或其盐。 上述衍生物 (I) 及其盐可用于抗溃疡剂。 本发明还提供了制备此类衍生物的工艺，以及在上述工艺中形成的化学中间体。 本发明还提供了包含上述衍生物的药物组合物。 本发明还提供了此类化合物在制造具有治疗价值的药物中的用途。