N-(3,6-dihydro-2H-pyridin-1-yl)-2-methylbenzamide | 81460-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,6-dihydro-2H-pyridin-1-yl)-2-methylbenzamide
• CAS: 81460-50-6
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: BDZCBTMHOMDXPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻甲基苯甲酰氯 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 N-(3,6-dihydro-2H-pyridin-1-yl)-2-methylbenzamide
  参考文献：
  名称：

  Synthesis of N-[[(substituted-phenyl)carbonyl]amino]-1,2,3,6-tetrahydropyridines with analgesic and hyperglycemic activity

  摘要：

  A group of N-[(phenylcarbonyl)amino]1-2,3,6-tetrahydropyridines, 5, were synthesized to determine the effect that changes in aromatic substitution on the phenyl ring have on analgesic, hyperglycemic, and antiinflammatory activities. All of the N-[(phenylcarbonyl)amino]-1,2,3,6-tetrahydropyridines 5 exhibited potent analgesic activity, relative to morphine, irrespective of the position and physicochemical properties of the aromatic substituent. Pretreatment with naloxone did not alter the analgesic activity of the 4-fluorophenyl derivative 5P. N-[[(2-Fluorophenyl)-carbonyl]amino]-1,2,3,6-tetrahydropyridine (5n) was one of the most active hyperglycemic agents, elevating blood glucose 213 and 127% at 2 and 4 h after a 100 mg/kg po dose. Incorporation of aromatic substituents into the 3 and 4 positions of 1 abolished antiinflammatory activity.

  DOI：

  10.1021/jm00348a021

文献信息

• YEUNG, J. M.;CORLETO, L. A.;KNAUS, E. E., J. MED. CHEM., 1982, 25, N 6, 720-723
  作者：YEUNG, J. M.、CORLETO, L. A.、KNAUS, E. E.

  DOI：——

  日期：——
• Synthesis of N-[[(substituted-phenyl)carbonyl]amino]-1,2,3,6-tetrahydropyridines with analgesic and hyperglycemic activity
  作者：Jupita M. Yeung、Linda A. Corleto、Edward E. Knaus

  DOI：10.1021/jm00348a021

  日期：1982.6

  A group of N-[(phenylcarbonyl)amino]1-2,3,6-tetrahydropyridines, 5, were synthesized to determine the effect that changes in aromatic substitution on the phenyl ring have on analgesic, hyperglycemic, and antiinflammatory activities. All of the N-[(phenylcarbonyl)amino]-1,2,3,6-tetrahydropyridines 5 exhibited potent analgesic activity, relative to morphine, irrespective of the position and physicochemical properties of the aromatic substituent. Pretreatment with naloxone did not alter the analgesic activity of the 4-fluorophenyl derivative 5P. N-[[(2-Fluorophenyl)-carbonyl]amino]-1,2,3,6-tetrahydropyridine (5n) was one of the most active hyperglycemic agents, elevating blood glucose 213 and 127% at 2 and 4 h after a 100 mg/kg po dose. Incorporation of aromatic substituents into the 3 and 4 positions of 1 abolished antiinflammatory activity.