methyl N'-[4-[6-(acetamidomethyl)pyridin-2-yl]-1,3-thiazol-2-yl]carbamimidothioate | 763894-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl N'-[4-[6-(acetamidomethyl)pyridin-2-yl]-1,3-thiazol-2-yl]carbamimidothioate
• CAS: 763894-96-8
• 化学式: C₁₃H₁₅N₅OS₂
• 分子量: 321.427
• InChiKey: XWWMOPQXEAAPHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(甲硫基)乙胺 、 methyl N'-[4-[6-(acetamidomethyl)pyridin-2-yl]-1,3-thiazol-2-yl]carbamimidothioate 以 乙醇 为溶剂， 反应 48.0h， 生成 N-[[6-[2-[[N'-(2-methylsulfanylethyl)carbamimidoyl]amino]-1,3-thiazol-4-yl]pyridin-2-yl]methyl]acetamide
  参考文献：
  名称：

  Anti-Helicobacter pylori Agents. 5. 2-(Substituted guanidino)-4-arylthiazoles and Aryloxazole Analogues

  摘要：

  To extend the SAR study of guanidinothiazoles as a structurally novel class of anti-H. pylori agents, a series of 2-(substituted guanidino)-4-arylthiazoles and some 4-aryloxazole analogues were synthesized and evaluated for antimicrobial activity against H. pylori, Some of them were also subjected to H2 antagonist and gastric antisecretory assays. Several arylthiazoles were identified as potent anti-H. pylori agents, and of these, thienylthiazole derivative 44 exhibited the strongest activity (MIC = 0.0065 mug/mL) among the compounds obtained in our guanidinothiazole studies. Although 44 was void of H2 antagonist activity, pyridylthiazole derivative 39 had both potent anti-H. pylori and H2 antagonist activities. Thiazolylthiazole derivative 46 also showed potent anti-H. pylori activity, but the H2 antagonist activity was weak. On the other hand, no attractive activities were found in pyrimidyl, oxazolyl, isoxazolyl, imidazolyl, and oxadiazolylthiazole derivatives. The anti-H. pylori activity of the aryloxazole analogues was weaker than those of the corresponding arylthiazole derivatives, though they had potent H2 antagonist activity.

  DOI：

  10.1021/jm010217j
• 作为产物：
  描述：

  乙酰胺,N-[[6-(溴乙酰基)-2-吡啶基]甲基]- 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 10.0h， 生成 methyl N'-[4-[6-(acetamidomethyl)pyridin-2-yl]-1,3-thiazol-2-yl]carbamimidothioate
  参考文献：
  名称：

  Anti-Helicobacter pylori Agents. 5. 2-(Substituted guanidino)-4-arylthiazoles and Aryloxazole Analogues

  摘要：

  To extend the SAR study of guanidinothiazoles as a structurally novel class of anti-H. pylori agents, a series of 2-(substituted guanidino)-4-arylthiazoles and some 4-aryloxazole analogues were synthesized and evaluated for antimicrobial activity against H. pylori, Some of them were also subjected to H2 antagonist and gastric antisecretory assays. Several arylthiazoles were identified as potent anti-H. pylori agents, and of these, thienylthiazole derivative 44 exhibited the strongest activity (MIC = 0.0065 mug/mL) among the compounds obtained in our guanidinothiazole studies. Although 44 was void of H2 antagonist activity, pyridylthiazole derivative 39 had both potent anti-H. pylori and H2 antagonist activities. Thiazolylthiazole derivative 46 also showed potent anti-H. pylori activity, but the H2 antagonist activity was weak. On the other hand, no attractive activities were found in pyrimidyl, oxazolyl, isoxazolyl, imidazolyl, and oxadiazolylthiazole derivatives. The anti-H. pylori activity of the aryloxazole analogues was weaker than those of the corresponding arylthiazole derivatives, though they had potent H2 antagonist activity.

  DOI：

  10.1021/jm010217j

文献信息

• New thiazole derivatives, processes for the preparation thereof and pharmaceutical compositon comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0417751A2

  公开（公告）日：1991-03-20

  A compound of the formula : wherein R' is amino which may have suitable substituent ( s). hydroxy. halogen, cyano, acyl, heterocyclic thio, heterocyclic group or a group of the formula : in which R4 is hydrogen, cyano or acyl. and R5 is amino or lower alkoxy. R2 and R3 are each hydrogen, acyl or lower alkyl which may have halogen: or R2 and R3 are linked together to form lower alkylene. in which R6 is hydrogen or halogen, and A is bond or lower alkylene, provided that when R1 is amino which may have suitable substituent(s) and A is bond; or R1 is lower alkylthioureido and A is lower alkylene, then and pharmaceutically acceptable salt thereof, processes for their preparation and pharmaceutical compositions comprising them as an active. ingredient.

  式中的化合物 其中 R'为氨基，可具有合适的取代基（s）、羟基、卤素、氰基、酰基、杂环硫基、杂环基团或式......的基团： 其中 R4 是氢、氰基或酰基。 R5 是氨基或低级烷氧基。 R2 和 R3 各为氢、酰基或低级烷基，其中可含卤素：或 R2 和 R3 连接在一起形成低级亚烷基。 其中 R6 是氢或卤素，以及 A 是键或低级亚烷基、 条件是 当 R1 是氨基，可有适当的取代基，且 A 为键；或 R1 为低级烷基硫脲基，且 A 为低级亚烷基时 且 A 为低级亚烷基，则 以及它们的药学上可接受的盐、它们的制备方法和含有它们作为活性成分的药物组合物。
• THIAZOLE DERIVATIVES
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0575614A1

  公开（公告）日：1993-12-29
• US5364871A
  申请人：——

  公开号：US5364871A

  公开（公告）日：1994-11-15
• US5371097A
  申请人：——

  公开号：US5371097A

  公开（公告）日：1994-12-06
• [EN] THIAZOLE DERIVATIVES
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1992016526A1

  公开（公告）日：1992-10-01

  (EN) Thiazole derivatives of formula (I) or a salt thereof, which are useful as antiulcer agent, H2-receptor antagonist or antimicrobial agent.(FR) L'invention se rapporte à des dérivés de thiazole représentés par la formule (I), ou à un sel de ces dérivés, qui sont utiles comme agent antiulcéreux, comme antagoniste des récepteurs de H2 ou comme agent antimicrobien.