3-(4-hydroxybenzoyl)-8-methylimidazo<1,2-a>pyridine | 114604-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-hydroxybenzoyl)-8-methylimidazo<1,2-a>pyridine
• 英文别名: 3-(4-hydroxybenzoyl)-8-methylimidazo[1,2-a]pyridine；(4-hydroxyphenyl)-(8-methylimidazo[1,2-a]pyridin-3-yl)methanone
• CAS: 114604-81-8
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: GESJXVMRFNPGJL-UHFFFAOYSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxybenzoyl)-8-methylimidazo<1,2-a>pyridine 、 N-(3-氯丙基)二丁基胺 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以31%的产率得到3-{4-[(dibutylamino)propoxy]benzoyl}-8-methylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity

  摘要：

  A series of imidazo-fused heterocycles substituted with an aryloxy)alkylamine side chain were prepared as modifications to butoprozine (I) and found to possess calcium channel blocking activity similar in potency to that of bepridil in trachea smooth muscle and similar to that of verapamil in nitrendipine binding affinity in rabbit cardiac muscle. Of the various imidazo-fused heterocycles prepared, the imidazo[1,2-a]pyridines were also found to be potent local anesthetic agents. While most compounds in this series were equipotent to lidocaine in our initial screen, compounds 2 and 35 showed local anesthetic activity approximately 100 times more potent than lidocaine in our preliminary assays. These compounds represent a novel structural class of local anesthetic agents, and compound 2 is under further investigation.

  DOI：

  10.1021/jm00119a026
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 3-(4-hydroxybenzoyl)-8-methylimidazo<1,2-a>pyridine
  参考文献：
  名称：

  Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity

  摘要：

  A series of imidazo-fused heterocycles substituted with an aryloxy)alkylamine side chain were prepared as modifications to butoprozine (I) and found to possess calcium channel blocking activity similar in potency to that of bepridil in trachea smooth muscle and similar to that of verapamil in nitrendipine binding affinity in rabbit cardiac muscle. Of the various imidazo-fused heterocycles prepared, the imidazo[1,2-a]pyridines were also found to be potent local anesthetic agents. While most compounds in this series were equipotent to lidocaine in our initial screen, compounds 2 and 35 showed local anesthetic activity approximately 100 times more potent than lidocaine in our preliminary assays. These compounds represent a novel structural class of local anesthetic agents, and compound 2 is under further investigation.

  DOI：

  10.1021/jm00119a026

文献信息

• 2- or 3-aryl substituted imidazo[1,2-a]pyridines and their use as
  申请人：Ortho Pharmaceutical Corporation

  公开号：US04791117A1

  公开（公告）日：1988-12-13

  Novel 2- or 3- aryl substituted imidazo[1,2-a]pyridines and their synthesis are described. The compounds have local anesthetic properties and are useful as local anesthetic agents, calcium channel blocking agents and antisecretory agents.

  描述了新型2-或3-芳基取代的咪唑[1,2-a]吡啶类化合物及其合成方法。这些化合物具有局部麻醉性能，并可用作局部麻醉剂、钙通道阻断剂和抗分泌剂。
• 2- Or 3- aryl substituted imidazo [1,2-a]pyridines
  申请人：Ortho Pharmaceutical Corporation

  公开号：US04727145A1

  公开（公告）日：1988-02-23

  Novel 2- or 3- aryl substituted imidazo[1,2-a]pyridines and their synthesis are described. The compounds have local anesthetic properties and are useful as local anesthetic agents.

  描述了新型2-或3-芳基取代的咪唑并[1,2-a]吡啶及其合成。这些化合物具有局部麻醉特性，可用作局部麻醉剂。
• 2- or 3-aryl substituted imidazo(1,2-A)pyridines and their use as
  申请人：Ortho Pharmaceutical Corporation

  公开号：US04871745A1

  公开（公告）日：1989-10-03

  Novel 2- or 3- aryl substituted imidazo[1,2-a]pyridines and their synthesis are described. The compounds have local anesthetic properties and are useful as local anesthetic agents, calcium channel blocking agents and antisecretory agents.

  本文介绍了2-或3-芳基取代的咪唑[1,2-a]吡啶类化合物及其合成方法。这些化合物具有局部麻醉性质，可用作局部麻醉剂、钙通道阻滞剂和抗分泌剂。
• 2- or 3- Aryl substituted imidazo [1,2-a] pyridines
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0261912A2

  公开（公告）日：1988-03-30

  Novel 2- or 3- aryl substituted imidazo[1,2-a]pyridines and their synthesis are described. The compounds have local anesthetic properties and are useful as local anesthetic agents, calcium channel blocking agents and antisecretory acents.

  介绍了新型 2-或 3-芳基取代咪唑并[1,2-a]吡啶及其合成方法，这些化合物具有局部麻醉特性，可用作局部麻醉剂、钙通道阻滞剂和抗分泌剂。
• PRESS, JEFFERY B.
  作者：PRESS, JEFFERY B.

  DOI：——

  日期：——