N-[4-(2-Bromo-acetyl)-thiazol-2-ylmethyl]-acetamide | 135450-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[4-(2-Bromo-acetyl)-thiazol-2-ylmethyl]-acetamide
• 英文别名: 2-Acetylaminomethyl-4-bromoacetylthiazole；N-[[4-(2-bromoacetyl)-1,3-thiazol-2-yl]methyl]acetamide
• CAS: 135450-84-9
• 化学式: C₈H₉BrN₂O₂S
• 分子量: 277.142
• InChiKey: NVJVDVVIRNMUJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[4-(2-Bromo-acetyl)-thiazol-2-ylmethyl]-acetamide 、 [2-(2-methoxyphenyl)ethylamidino]thiourea 在 碳酸氢钠 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.33h， 以48%的产率得到N-(2'-{N'-[2-(2-Methoxy-phenyl)-ethyl]-guanidino}-[4,4']bithiazolyl-2-ylmethyl)-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：

  2-acetamidomethyl-4-acetylthiazole 在 溴 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 生成 N-[4-(2-Bromo-acetyl)-thiazol-2-ylmethyl]-acetamide
  参考文献：
  名称：

  抗溃疡药物的研究。VI。作为有效的组胺H2受体拮抗剂的4-Furyl-2-guanidinothiazoles和相关化合物。

  摘要：

  合成了一系列的4-呋喃基-2-胍基噻唑衍生物和相关化合物，并评估了组胺H2-受体拮抗剂和胃酸的抗分泌活性。其中，化合物I-17，I-48和I-49在这些测试中显示出高活性。另外，化合物I-17对由压力，乙醇和HCl-阿司匹林诱导的每个胃溃疡具有有效的抑制活性。另一方面，化合物I-48显示出对幽门螺杆菌的抗菌活性，并且效力远强于临床使用的H2-拮抗剂。讨论了一些构效关系。

  DOI：

  10.1248/cpb.40.2432

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。
• 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