2-[2-(1-methyl-1H-pyrrol-2-yl)-ethyl]-2,3,4,9-tetrahydro-pyrido[3,4-b]indol-1-one | 369652-09-5

• 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: 2-[2-(1-methyl-1H-pyrrol-2-yl)-ethyl]-2,3,4,9-tetrahydro-pyrido[3,4-b]indol-1-one
• CAS: 369652-09-5
• 化学式: C₁₈H₁₉N₃O
• 分子量: 293.368
• InChiKey: OIDZYVFHBJFQEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  41.03
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-[2-(1-methyl-1H-pyrrol-2-yl)-ethyl]-2,3,4,9-tetrahydro-pyrido[3,4-b]indol-1-one 在 三氯氧磷 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 23.0h， 生成 3,6-dimethyl-4,5,7,8,13,13b-hexahydro-3H-indolo[2,3-a]pyrrolo[2,3-h]quinolizinium iodide
  参考文献：
  名称：

  Synthesis and 5-HT2A Antagonist Activity of Derivatives of the Novel Heterocycles Indolo[3,2-d]pyrrolo[3,2-g]azecine and Benzo[d]pyrrolo[3,2-g]azecine compared to the Benz[d]indolo[2,3-g]azecine Derivative LE 300

  摘要：

  An indolo[3,2-d]pyrrolo[3,2-g]azecine and a benzo[d]pyrrolo[3,2-glazecine analogue of the potent dopamine receptor antagonist LE 300 {7-methyl-6,7,8,9,14,15-hexahydro-5H-benz[d]indolo[2,3-g]azecine) have been prepared in mufti-step reactions via C-N bond cleavage of corresponding quaternary N-methylquinolizinium iodides. LE 300, the target compounds and two precursor quinolizines have been tested in vitro for antagonist activity at 5-HT2A receptors (rat tail artery) and Hl receptors {guinea-pig ileum), respectively. LE 300 and compound 19 {3,6-dimethyl-4,5,6,7,8,13-hexahydro-3H-benzo[d]pyrrolo[3,2-glazecine) competitively inhibited S-HT-induced contractions with similar nanomolar potency (pA(2) = 8.32 and 8.01, respectively) but were less active than the reference antagonist ketanserin (pA(2) = 9.55). Compound 19 displayed moderate H-1-antihistaminic activity in the guinea-pig ileum assay (pA(2) = 7.37).

  DOI：

  10.1002/1521-4184(200107)334:7<241::aid-ardp241>3.0.co;2-b
• 作为产物：
  描述：

  1H-吡咯,1-甲基-2-[(1E)-2-硝基乙烯基]- 在 lithium aluminium tetrahydride 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 72.0h， 生成 2-[2-(1-methyl-1H-pyrrol-2-yl)-ethyl]-2,3,4,9-tetrahydro-pyrido[3,4-b]indol-1-one
  参考文献：
  名称：

  Synthesis and 5-HT2A Antagonist Activity of Derivatives of the Novel Heterocycles Indolo[3,2-d]pyrrolo[3,2-g]azecine and Benzo[d]pyrrolo[3,2-g]azecine compared to the Benz[d]indolo[2,3-g]azecine Derivative LE 300

  摘要：

  An indolo[3,2-d]pyrrolo[3,2-g]azecine and a benzo[d]pyrrolo[3,2-glazecine analogue of the potent dopamine receptor antagonist LE 300 {7-methyl-6,7,8,9,14,15-hexahydro-5H-benz[d]indolo[2,3-g]azecine) have been prepared in mufti-step reactions via C-N bond cleavage of corresponding quaternary N-methylquinolizinium iodides. LE 300, the target compounds and two precursor quinolizines have been tested in vitro for antagonist activity at 5-HT2A receptors (rat tail artery) and Hl receptors {guinea-pig ileum), respectively. LE 300 and compound 19 {3,6-dimethyl-4,5,6,7,8,13-hexahydro-3H-benzo[d]pyrrolo[3,2-glazecine) competitively inhibited S-HT-induced contractions with similar nanomolar potency (pA(2) = 8.32 and 8.01, respectively) but were less active than the reference antagonist ketanserin (pA(2) = 9.55). Compound 19 displayed moderate H-1-antihistaminic activity in the guinea-pig ileum assay (pA(2) = 7.37).

  DOI：

  10.1002/1521-4184(200107)334:7<241::aid-ardp241>3.0.co;2-b