N-[4-(Quinolin-5-yl-hydrazono)-cyclohexyl]-acetamide | 102745-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[4-(Quinolin-5-yl-hydrazono)-cyclohexyl]-acetamide
• CAS: 102745-87-9
• 化学式: C₁₇H₂₀N₄O
• 分子量: 296.372
• InChiKey: XSGDJLLWCSLODB-ZHZULCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.38
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[4-(Quinolin-5-yl-hydrazono)-cyclohexyl]-acetamide 在 硫酸 、 sodium hydride 作用下， 以 溶剂黄146 为溶剂， 反应 1.17h， 生成 N-(11-methyl-7,8,9,10-tetrahydro-11H-pyrido<3,2-a>carbazol-8-yl)acetamide
  参考文献：
  名称：

  Ligand-receptor interactions via hydrogen-bond formation. Synthesis and pharmacological evaluation of pyrrolo and pyrido analogs of the cardiotonic agent 7-hydroxycyclindole

  摘要：

  The syntheses of N,N-dimethyl-6,7,8,9-tetrahydro-3H,10H-pyrrolo[3,2-a] carbazol-7-amine (8), N,N-dimethyl-7,8,9,10-tetrahydro-11H-pyrido[3,2-a] carbazol-8-amine (9a), and the N,N,11-trimethyl analogue (9b) are described. The in vitro inotropic activity of these compounds, as well as the known cardiotonics amrinone and 7-hydroxycyclindole (7), was investigated. Compound 8, a pyrrolo analogue of 7, was devoid of inotropic activity, while the pyrido analogues 9 were equiactive to 7 and amrinone. These results suggest that the hydroxyl group of 7 functions as an H-bond acceptor, rather than a donor, and that on interaction of 7, and the pyrido analogues 9, with a common receptor, an orbital occupied by one of the oxygen lone pair electrons of 7 must assume the same orientation as the orbital occupied by the pyridine nitrogen lone pair.

  DOI：

  10.1021/jm00158a022
• 作为产物：
  描述：

  对乙酰氨基酚 在 镍 sodium dichromate 、 硫酸 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 180.0 ℃ 、12.07 MPa 条件下， 反应 3.66h， 生成 N-[4-(Quinolin-5-yl-hydrazono)-cyclohexyl]-acetamide
  参考文献：
  名称：

  Ligand-receptor interactions via hydrogen-bond formation. Synthesis and pharmacological evaluation of pyrrolo and pyrido analogs of the cardiotonic agent 7-hydroxycyclindole

  摘要：

  The syntheses of N,N-dimethyl-6,7,8,9-tetrahydro-3H,10H-pyrrolo[3,2-a] carbazol-7-amine (8), N,N-dimethyl-7,8,9,10-tetrahydro-11H-pyrido[3,2-a] carbazol-8-amine (9a), and the N,N,11-trimethyl analogue (9b) are described. The in vitro inotropic activity of these compounds, as well as the known cardiotonics amrinone and 7-hydroxycyclindole (7), was investigated. Compound 8, a pyrrolo analogue of 7, was devoid of inotropic activity, while the pyrido analogues 9 were equiactive to 7 and amrinone. These results suggest that the hydroxyl group of 7 functions as an H-bond acceptor, rather than a donor, and that on interaction of 7, and the pyrido analogues 9, with a common receptor, an orbital occupied by one of the oxygen lone pair electrons of 7 must assume the same orientation as the orbital occupied by the pyridine nitrogen lone pair.

  DOI：

  10.1021/jm00158a022

文献信息

• DIONNE G.; HUMBER L. G.; ASSELIN A.; MCQUILLAN J.; TREASURYWALA A. M., J. MED. CHEM., 29,(1986) N 8, 1452-1457
  作者：DIONNE G.、 HUMBER L. G.、 ASSELIN A.、 MCQUILLAN J.、 TREASURYWALA A. M.

  DOI：——

  日期：——