3-[4-[6-(3-Oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl]phenyl]prop-2-enal | 214958-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[4-[6-(3-Oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl]phenyl]prop-2-enal
• CAS: 214958-40-4
• 化学式: C₁₉H₁₄N₂O₂
• 分子量: 302.332
• InChiKey: ULOGAXDYVSGORE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-二氰咪唑-2-肼溴化氢 、 3-[4-[6-(3-Oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl]phenyl]prop-2-enal 在 氢溴酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 N-[3-[4-[6-[3-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)prop-1-enyl]imidazo[1,2-a]pyridin-2-yl]phenyl]prop-2-enylideneamino]-4,5-dihydro-1H-imidazol-2-amine;hydrobromide
  参考文献：
  名称：

  Bis-Cationic Heteroaromatics as Macrofilaricides:  Synthesis of Bis-Amidine and Bis-Guanylhydrazone Derivatives of Substituted Imidazo[1,2-a]pyridines

  摘要：

  A series of guanylhydrazone, amidine, and hydrazone derivatives of 2-phenylimidazo[1,2-a]pyridine have been prepared and evaluated for macrofilarial activity against Acanthocheilonema viteae and Brugia pahangi in jirds. Compounds with 4',6-bis-substitution by cyclic guanylhydrazone groups show activity. 4',6-Bis-amidines show some activity but are more toxic; 4'- or 6-monosubstituted compounds are inactive. 2,6-Bis-substituted compounds lacking the phenyl ring are inactive. 4',6-Bis-substituted compounds having additional double bonds inserted between the heterocyclic ring and the phenyl ring or between the substituent and the ring system show reduced activity.

  DOI：

  10.1021/jm9803368
• 作为产物：
  描述：

  6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine 在 正丁基锂 、 四甲基乙二胺 、 草酸 作用下， 反应 2.5h， 生成 3-[4-[6-(3-Oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl]phenyl]prop-2-enal
  参考文献：
  名称：

  Bis-Cationic Heteroaromatics as Macrofilaricides:  Synthesis of Bis-Amidine and Bis-Guanylhydrazone Derivatives of Substituted Imidazo[1,2-a]pyridines

  摘要：

  A series of guanylhydrazone, amidine, and hydrazone derivatives of 2-phenylimidazo[1,2-a]pyridine have been prepared and evaluated for macrofilarial activity against Acanthocheilonema viteae and Brugia pahangi in jirds. Compounds with 4',6-bis-substitution by cyclic guanylhydrazone groups show activity. 4',6-Bis-amidines show some activity but are more toxic; 4'- or 6-monosubstituted compounds are inactive. 2,6-Bis-substituted compounds lacking the phenyl ring are inactive. 4',6-Bis-substituted compounds having additional double bonds inserted between the heterocyclic ring and the phenyl ring or between the substituent and the ring system show reduced activity.

  DOI：

  10.1021/jm9803368