3-(2-bromo-ethyl)-1H-indole-2-carboxylic acid ethyl ester | 369652-08-4

• 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: 3-(2-bromo-ethyl)-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: 3-(Bromo-ethyl)-2-ethoxycarbonylindole；ethyl 3-(2-bromoethyl)-1H-indole-2-carboxylate
• CAS: 369652-08-4
• 化学式: C₁₃H₁₄BrNO₂
• 分子量: 296.164
• InChiKey: XGHJRCDKFAHUQB-UHFFFAOYSA-N

物化性质

• 沸点：
  437.0±35.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-bromo-ethyl)-1H-indole-2-carboxylic acid ethyl ester 在 potassium carbonate 、 potassium iodide 、 三氯氧磷 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 95.0h， 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：

  4,9-Dihydropyrano<3,4-b>indol-1(3H)-on 、 乙醇 在 氢溴酸 作用下， 反应 18.0h， 以73%的产率得到3-(2-bromo-ethyl)-1H-indole-2-carboxylic acid ethyl ester
  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).