N,N-dimethyl-7,8,9,10-tetrahydro-11H-pyrido<3,2-a>carbazol-8-amine | 102745-91-5

• 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,N-dimethyl-7,8,9,10-tetrahydro-11H-pyrido<3,2-a>carbazol-8-amine
• 英文别名: N,N-dimethyl-7,8,9,10-tetrahydro-11H-pyrido[3,2-a]carbazol-8-amine；N,N-dimethyl-8,9,10,11-tetrahydro-7H-pyrido[3,2-a]carbazol-8-amine
• CAS: 102745-91-5
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.358
• InChiKey: MNMJMICCAVKPLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 7,8,9,10-tetrahydro-11H-pyrido<3,2-a>carbazol-8-amine 在 甲酸 作用下， 以 水 为溶剂， 反应 20.0h， 以2.49 g的产率得到N,N-dimethyl-7,8,9,10-tetrahydro-11H-pyrido<3,2-a>carbazol-8-amine
  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

• Ligand-receptor interactions via hydrogen-bond formation. Synthesis and pharmacological evaluation of pyrrolo and pyrido analogs of the cardiotonic agent 7-hydroxycyclindole
  作者：Gervais Dionne、Leslie G. Humber、Andre Asselin、Juanita McQuillan、Adi M. Treasurywala

  DOI：10.1021/jm00158a022

  日期：1986.8

  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.