N-{5-[2-(N'-Butyl-guanidino)-thiazol-4-yl]-thiophen-2-ylmethyl}-acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-{5-[2-(N'-Butyl-guanidino)-thiazol-4-yl]-thiophen-2-ylmethyl}-acetamide
• 英文别名: N-[[5-[2-[(N'-butylcarbamimidoyl)amino]-1,3-thiazol-4-yl]thiophen-2-yl]methyl]acetamide
• 化学式: C₁₅H₂₁N₅OS₂
• 分子量: 351.497
• InChiKey: AVTNDZMJKBCTES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  n-butylamidinothiourea 、 N-[5-(2-Chloro-acetyl)-thiophen-2-ylmethyl]-acetamide 在 碳酸氢钠 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.33h， 以53%的产率得到N-{5-[2-(N'-Butyl-guanidino)-thiazol-4-yl]-thiophen-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

文献信息

• [EN] THIENYLTHIAZOLE DERIVATIVES<br/>[FR] DERIVES DE THIENYLTHIAZOLE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1994029304A1

  公开（公告）日：1994-12-22

  (EN) This invention relates to new thienylthiazol derivatives having antiulcer activity, H2-receptor antagonism and antimicrobial activity, and represented by general formula (I), wherein R1 is hydrogen or alkyl optionally substituted with alkoxy, R2 is hydrogen or alkyl optionally substituted with alkoxy, R3 is hydrogen or lower alkyl, R4 is amino optionally substituted with acyl, A is a single bond or lower alkylene, and Q is hydrogen or lower alkyl, provided that when R1 and R2 are both hydrogen, then (1) R4 is amino substituted with esterified carboxy, or (2) Q is lower alkyl, and pharmaceutically acceptable salts thereof, to processes for the preparation thereof and to a pharmaceutical composition comprising the same.(FR) Nouveaux dérivés de thiénylthiazole présentant une activité anti-ulcéreuse, antagoniste des récepteurs H2 et antimicrobienne, représentés par la formule générale (I) dans laquelle R1 est l'hydrogène ou un alkyle facultativement substitué par un alcoxy; R2 est l'hydrogène ou un alkyle facutativement substitué par un alcoxy; R3 est l'hydrogène ou un alkyle inférieur; R4 est un amino facultativement substitué par un acyle; A est une liaison unique ou un alkylène inférieur; et Q est l'hydrogène ou un alkyle inférieur, à condition que, lorsque R1 et R2 sont tous les deux de l'hydrogène, (1) R4 est un amino substitué par un carboxy estérifié, ou (2) Q est un alkyle inférieur. Sont également décrits des sels pharmaceutiquement acceptables de ces dérivés, des procédés de préparation de ces dérivés et de ces sels, ainsi qu'une composition pharmaceutique les renfermant.