3-methyl-3,4,5,7,8,12b-hexahydro-benzo[a]pyrrolo[2,3-h]quinolizine | 369652-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 3-methyl-3,4,5,7,8,12b-hexahydro-benzo[a]pyrrolo[2,3-h]quinolizine
• 英文别名: 14-Methyl-10,14-diazatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,13(17),15-pentaene
• CAS: 369652-14-2
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: YMBSJPOFTIRLJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-3,4,5,7,8,12b-hexahydro-benzo[a]pyrrolo[2,3-h]quinolizine 在 氨 、 sodium 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 18.0h， 生成 3,6-dimethyl-4,5,6,7,8,13-hexahydro-3H-benzo[d]pyrrolo[3,2-g]azecine
  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：

  2-(2-氨基乙基)-1-甲基吡咯烷 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 51.0h， 生成 3-methyl-3,4,5,7,8,12b-hexahydro-benzo[a]pyrrolo[2,3-h]quinolizine
  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

文献信息

• 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
  作者：Sherif A. F. Rostom、Ahmed M. Farghaly、Farid S. G. Soliman、Mona M. El-Semary、Sigurd Elz、Jochen Lehmann

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

  日期：2001.7

  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).