N-(benzoylamino)-5-(3-hydroxypropyl)-1,2,3,6-tetrahydropyridine | 66611-58-3

• 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-(benzoylamino)-5-(3-hydroxypropyl)-1,2,3,6-tetrahydropyridine
• 英文别名: N-(Benzoylimino)-3-(3-hydroxypropyl)-1,2,5,6-tetrahydropyridin；N-[3,6-Dihydro-5-(3-hydroxypropyl)-1(2H)-pyridinyl]benzamide；N-[5-(3-hydroxypropyl)-3,6-dihydro-2H-pyridin-1-yl]benzamide
• CAS: 66611-58-3
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: HQABDQCAXLWAHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(benzoylamino)-5-(3-hydroxypropyl)-1,2,3,6-tetrahydropyridine 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 5-(3-methoxypropyl)-N-(3,6-dihydro-1(2H)-pyridinyl)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：

  N-(benzoylimino)-3-(3-hydroxypropyl)pyridinium ylide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以59%的产率得到N-(benzoylamino)-5-(3-hydroxypropyl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  某些N- [吡啶基（苯基）羰基氨基]羟烷基-（苄基）-1,2,3,6-四氢吡啶的合成作为潜在的抗炎药

  摘要：

  已知1,2,3,6-四氢吡啶具有镇痛，抗炎，高血糖和降血糖活性。通过使1-氯-2，4-二硝基苯与羟丙基，羟甲基和苄基取代的吡啶2反应形成取代的2，4-二硝基苯基吡啶鎓氯化物3。用吡啶基羰基酰肼或苯甲酰肼4攻击吡啶鎓氯化物3，得到可分离的2,4-二硝基苯胺基衍生物5，当在水：对二恶烷混合物（1：4 v / v）中回流时进行水解，得到吡啶鎓酰化物6。硼氢化钠还原量为6将其在0°C的纯乙醇中放置4-6小时，从而以高收率分离出1,2,3,6-四氢吡啶7。

  DOI：

  10.1002/jhet.5570320151

文献信息

• 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 of some<i>N</i>-[pyridyl(phenyl)carbonylamino]hydroxyalkyl-(benzyl)-1,2,3,6-tetrahydropyridines as potential anti-inflammatory agents
  作者：Kode Nageswara Rao、Kinfe K. Redda、Folakemi Y. Onayemi、Hailemichael Melles、Jongoh Choi

  DOI：10.1002/jhet.5570320151

  日期：1995.1

  hydroxymethyl and benzyl substituted pyridines 2. Attack of the pyridinium chlorides 3 with pyridylcarbonyl hydrazides or benzoyl hydrazides 4 gave the isolable 2,4-dinitroanilino derivative 5 which underwent hydrolysis when refluxed in water:p-dioxane mixture (1:4 v/v) to afford the pyridinium ylides 6. Sodium borohydride reduction of 6 in absolute ethanol at 0° for 4–6 hours resulted in the isolation

  已知1,2,3,6-四氢吡啶具有镇痛，抗炎，高血糖和降血糖活性。通过使1-氯-2，4-二硝基苯与羟丙基，羟甲基和苄基取代的吡啶2反应形成取代的2，4-二硝基苯基吡啶鎓氯化物3。用吡啶基羰基酰肼或苯甲酰肼4攻击吡啶鎓氯化物3，得到可分离的2,4-二硝基苯胺基衍生物5，当在水：对二恶烷混合物（1：4 v / v）中回流时进行水解，得到吡啶鎓酰化物6。硼氢化钠还原量为6将其在0°C的纯乙醇中放置4-6小时，从而以高收率分离出1,2,3,6-四氢吡啶7。
• 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.