N-(7-amino-1,2,3,4-tetrahydro-9H-carbazol-3-yl)acetamide | 102745-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(7-amino-1,2,3,4-tetrahydro-9H-carbazol-3-yl)acetamide
• 英文别名: N-(7-amino-2,3,4,9-tetrahydro-1H-carbazol-3-yl)acetamide
• CAS: 102745-78-8
• 化学式: C₁₄H₁₇N₃O
• 分子量: 243.308
• InChiKey: WXUDTDAHFJLHKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  567.8±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(7-amino-1,2,3,4-tetrahydro-9H-carbazol-3-yl)acetamide 在 氢氧化钾 、 氨 、 sodium acetate 、 sodium 、 sodium cyanoborohydride 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 6.25h， 生成 6,7,8,9-tetrahydro-3H,10H-pyrrolo<3,2-a>carbazol-7-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
• 作为产物：
  描述：

  对乙酰氨基酚 在 palladium on activated charcoal 、 镍 盐酸 、 sodium dichromate 、 硫酸 、 氢气 作用下， 以 乙醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， 25.0~180.0 ℃ 、12.07 MPa 条件下， 反应 57.33h， 生成 N-(7-amino-1,2,3,4-tetrahydro-9H-carbazol-3-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

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：——
• 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.