[4-(3-Dibutylamino-propoxy)-phenyl]-imidazo[1,2-a]pyrimidin-3-yl-methanone | 115407-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4-(3-Dibutylamino-propoxy)-phenyl]-imidazo[1,2-a]pyrimidin-3-yl-methanone
• 英文别名: [4-[3-(Dibutylamino)propoxy]phenyl]-imidazo[1,2-a]pyrimidin-3-ylmethanone
• CAS: 115407-42-6
• 化学式: C₂₄H₃₂N₄O₂
• 分子量: 408.544
• InChiKey: DHDGRKQRYSSFRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-dimethyl-N'-pyrimidin-2-ylformamidine 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 [4-(3-Dibutylamino-propoxy)-phenyl]-imidazo[1,2-a]pyrimidin-3-yl-methanone
  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

• US4880824A
  申请人：——

  公开号：US4880824A

  公开（公告）日：1989-11-14
• Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity
  作者：Pauline J. Sanfilippo、Maud Urbanski、Jeffery B. Press、Barry Dubinsky、John B. Moore

  DOI：10.1021/jm00119a026

  日期：1988.11

  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.