5-methyl-N-(3,6-dihydro-1(2H)-pyridinyl)benzamide | 104642-66-2

• 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: 5-methyl-N-(3,6-dihydro-1(2H)-pyridinyl)benzamide
• 英文别名: N-(5-methyl-3,6-dihydro-2H-pyridin-1-yl)benzamide
• CAS: 104642-66-2
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: CXBFFTQYWOWSHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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

• 作为反应物：
  描述：

  5-methyl-N-(3,6-dihydro-1(2H)-pyridinyl)benzamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到3-methyl-N-(hexahydropyridinyl)benzamide
  参考文献：
  名称：

  Synthesis of N-(3,6-dihydro-1(2H)-pyridinyl)benzamides with hyperglycemic-hypoglycemic activity

  摘要：

  A group of N-(3,6-dihydro-1(2H)-pyridinyl)benzamides 7 were synthesized to determine the effect that the position and physicochemical properties of substituents attached to the heterocyclic ring have on blood glucose levels. 5-Methyl-N-(3,6-dihydro-1(2H)-pyridinyl)benzamide 7b was the most active hyperglycemic agent, elevating blood glucose 124% and 116% at 2 and 4 h, respectively, after a 100 mg/kg po dose. The most active hypoglycemic agent was the 4-acetyl analogue 7o, which was about 50% as active as chlorpropamide, lowering blood glucose 19% at 4 h after a 100 mg/kg po dose. A correlation between blood glucose levels and the partition coefficient P was not observed.

  DOI：

  10.1021/jm00384a018
• 作为产物：
  描述：

  1-(2,4-dinitrophenyl)-3-methylpyridinium chloride 在 sodium tetrahydroborate 、 水 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 28.0h， 生成 5-methyl-N-(3,6-dihydro-1(2H)-pyridinyl)benzamide
  参考文献：
  名称：

  一些N- [吡啶基（苯基）羰基氨基]甲基-1,2,3,6-四氢吡啶酮的合成与药理评价。

  摘要：

  与消炎痛相比，所有测试的化合物均显示出中度至良好的抗炎和镇痛作用。在甲基取代的四氢吡啶类化合物中，化合物11k是最有效的镇痛药，而11h是最有效的抗炎药。

  DOI：

  10.1002/jps.2600810515

文献信息

• CATES, LINDLEY A.;LI, VEN-SHUN, J. HETEROCYCL. CHEM., 24,(1987) N 6, 1635-1636
  作者：CATES, LINDLEY A.、LI, VEN-SHUN

  DOI：——

  日期：——
• YEUNG J. M.; KNAUS E. E., J. MED. CHEM., 30,(1987) N 1, 104-108
  作者：YEUNG J. M.、 KNAUS E. E.

  DOI：——

  日期：——
• Synthesis and pharmacological evaluation of some N‐[pyridyl(phenyl)carbonylamino]methyl‐1,2,3,6‐tetrahydropyridines
  作者：Kinfe K. Redda、Kode Nageswara Rao、S. Heiman、Hailemichael Melles

  DOI：10.1002/jps.2600810515

  日期：1992.5

  Reaction of some picolines 5 with 1-chloro-2,4-dinitrobenzene (6) in acetone furnished methyl-substituted 2,4-dinitrophenylpyridinium chlorides 7. Further reaction with phenyl(pyridyl)carbonyl hydrazides 8 at room temperature furnished isolable 2,4-dinitroanilino derivatives 9, which were then refluxed in a water:dioxane mixture (1:4, v/v) to furnish the methyl-substituted phenyl(pyridyl)carbonyl iminopyridinium

  与消炎痛相比，所有测试的化合物均显示出中度至良好的抗炎和镇痛作用。在甲基取代的四氢吡啶类化合物中，化合物11k是最有效的镇痛药，而11h是最有效的抗炎药。
• Synthesis of N-(3,6-dihydro-1(2H)-pyridinyl)benzamides with hyperglycemic-hypoglycemic activity
  作者：Jupita M. Yeung、Edward E. Knaus

  DOI：10.1021/jm00384a018

  日期：1987.1

  A group of N-(3,6-dihydro-1(2H)-pyridinyl)benzamides 7 were synthesized to determine the effect that the position and physicochemical properties of substituents attached to the heterocyclic ring have on blood glucose levels. 5-Methyl-N-(3,6-dihydro-1(2H)-pyridinyl)benzamide 7b was the most active hyperglycemic agent, elevating blood glucose 124% and 116% at 2 and 4 h, respectively, after a 100 mg/kg po dose. The most active hypoglycemic agent was the 4-acetyl analogue 7o, which was about 50% as active as chlorpropamide, lowering blood glucose 19% at 4 h after a 100 mg/kg po dose. A correlation between blood glucose levels and the partition coefficient P was not observed.