4-[6-(acetamidomethyl)pyridin-2-yl]-2-(thioureido)thiazole | 135450-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[6-(acetamidomethyl)pyridin-2-yl]-2-(thioureido)thiazole
• 英文别名: 4-(6-Acetylaminomethylpyridin-2-yl)-2-thioureidothiazole；N-[[6-[2-(carbamothioylamino)-1,3-thiazol-4-yl]pyridin-2-yl]methyl]acetamide
• CAS: 135450-50-9
• 化学式: C₁₂H₁₃N₅OS₂
• 分子量: 307.4
• InChiKey: OVTMUJYTNQJVOF-UHFFFAOYSA-N

物化性质

• 熔点：
  212-213 °C
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[6-(acetamidomethyl)pyridin-2-yl]-2-(thioureido)thiazole 以 甲醇 、 乙醇 为溶剂， 反应 51.0h， 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 7.0h， 生成 4-[6-(acetamidomethyl)pyridin-2-yl]-2-(thioureido)thiazole
  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

• Thiazole derivatives, processes for the preparation thereof and
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05371097A1

  公开（公告）日：1994-12-06

  A compound of the formula: ##STR1## wherein R.sup.1 is amino, acylamino, cyclo(lower)alkenylamino having amino and oxo, imido, triazolylamino, benzoisothiazolylamino, wherein each of said heterocyclicamino groups may be substituted by one or more substituent(s) selected from the group consisting of lower alkyl, amino and oxo, 2-cyano-3-lower alkylguanidino, 2-acyl-3-lower alkylguanidino, 2-acylguanidino, (1-lower alkylamino-2-nitrovinyl)amino, hydroxy, halogen, cyano, acyl, benzimidazolylthio, triazolyl substituted with amino, or a group of the formula: ##STR2## in which R.sup.4 is hydrogen, cyano, or acyl, and R.sup.5 is amino or lower alkoxy, R.sup.2 and R.sup.3 are each hydrogen, acyl or lower alkyl which may have halogen; or R.sup.2 and R.sup.3 are linked together to form lower alkylene, Y is ##STR3## in which R.sup.6 is hydrogen or halogen, and A is lower alkylene, or pharmaceutically acceptable salt thereof.

  该化合物的化学式为：##STR1## 其中R.sup.1为氨基，酰胺基，环(较低)烯基氨基，具有氨基和氧代的亚胺基，三唑基氨基，苯并异噻唑基氨基，其中所述的每个杂环氨基基团可以被选自较低烷基，氨基和氧代的一个或多个取代基取代，2-氰基-3-较低烷基胍基，2-酰基-3-较低烷基胍基，2-酰基胍基，(1-较低烷基氨基-2-硝基乙烯基)氨基，羟基，卤素，氰基，酰基，苯并咪唑基硫醚，三唑基被氨基取代，或一个化学式为：##STR2## 其中R.sup.4为氢，氰基或酰基，R.sup.5为氨基或较低烷氧基，R.sup.2和R.sup.3为氢，酰基或较低烷基，可以具有卤素；或R.sup.2和R.sup.3连接在一起形成较低烷基，Y为##STR3## 其中R.sup.6为氢或卤素，A为较低烷基，或其药学上可接受的盐。
• New thiazole derivatives, and pharmaceutical composition comprising the
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05364871A1

  公开（公告）日：1994-11-15

  A compound of the formula: ##STR1## wherein R.sup.1 is amino, ureido, lower alkanoylamino, lower alkoxycarbonylamino, lower alkylsulfonylamino, lower alkoxy(lower)alkanoylamino, mono or di or trihalo(lower)alkanoylamino, hydroxy(lower)alkanoylamino, protected hydroxy(lower)alkanoylamino, or a group of the formula: ##STR2## in which R.sup.4 is hydrogen or sulfamoyl, R.sup.5 is amino or lower alkoxy, R.sup.2 is hydrogen, lower alkyl, lower alkoxy(lower)alkyl, di(lower)alkylamino(lower)alkyl, (C.sub.3 -C.sub.7)-cycloalkyl, lower alkenyl or mono or di or trihalo(lower)alkyl; R.sup.3 is hydrogen or lower alkyl; or R.sup.2 and R.sup.3 are linked together to form lower alkylene, Y is ##STR3## in which R.sup.6 is hydrogen, A is lower alkylene, and W is NH; or R.sup.2 -W is piperidino or morpholino, or pharmaceutically acceptable salt thereof.

  该化合物的公式为：##STR1##其中R.sup.1为氨基，尿素基，较低的酰胺基，较低的烷氧羰基胺基，较低的烷基磺酰胺基，较低的烷氧（较低）酰胺基，单烷基或二或三卤代（较低）烷酰胺基，羟基（较低）烷酰胺基，保护羟基（较低）烷酰胺基，或公式：##STR2##其中R.sup.4为氢或磺酰基，R.sup.5为氨基或较低的烷氧基，R.sup.2为氢，较低的烷基，较低的烷氧（较低）烷基，二（较低）烷基氨基（较低）烷基，（C.sub.3-C.sub.7）-环烷基，较低的烯基或单烷基或二或三卤代（较低）烷基；R.sup.3为氢或较低的烷基；或者R.sup.2和R.sup.3相连形成较低的烷基，Y为##STR3##其中R.sup.6为氢，A为较低的烷基，W为NH；或R.sup.2-W为哌啶基或吗啉基，或其药学上可接受的盐。
• 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