3-ethyl-9-oxo-6,9-dihydro-3H-pyrrolo[3,2-f]quinoline-8-carboxylic acid ethyl ester | 853068-86-7

• 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: 3-ethyl-9-oxo-6,9-dihydro-3H-pyrrolo[3,2-f]quinoline-8-carboxylic acid ethyl ester
• CAS: 853068-86-7
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: XWJRQIIOAFTNDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.09
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-ethyl-9-oxo-6,9-dihydro-3H-pyrrolo[3,2-f]quinoline-8-carboxylic acid ethyl ester 在 三乙胺 、 三氯氧磷 作用下， 以 xylene 为溶剂， 生成
  参考文献：
  名称：

  Novel anellated pyrazoloquinolin-3-ones: synthesis and in vitro BZR activity

  摘要：

  A series of pyrazolo [4,3-c]pyrrolo[3,2-f]quinolin-3-one derivatives 6, 7a-c, 8a,b, 9a,b and 10-12 were synthesized as modified pyrazoloquinolinone analogs (PQs) and evaluated for their ability to inhibit radioligand to central and peripheral benzodiazepine receptors (BZRs) and their effect on GABA(A) α(1)β(2)γ(2L) receptors expressed in Xenopus laevis oocytes. Multistep synthesis starting from 5-nitroindole, via the Gould-Jacobs reaction to the quinoline nucleus, yielded key intermediates 9-chloro-3H-pyrrolo[3,2-f]quinoline-8-carboxylates. The reaction of the latter with methyl-hydrazine and various phenyl-hydrazines furnished the final compounds. In order to confirm the expected tetracyclic 2-substituted-2H-pyrazolopyrroloquinolin-3-one structure, IR spectrophotometric, mono-H-1 and C-13 and bi-dimensional spectrometric and HRMS analyses were carried out: all compounds were found to be 2-substituted 3-keto tautomers; compound 6 only differed because it turned out to be 1-methyl-2H-pyrazolo[4,3-c]pyrrolo[3,2-f]quinolin-3-olo. The results of this work are consistent with those previously reported for PQs: 7-9 show high potency in displacing specific [H-3]flunitrazepam from its receptor site; no compound was active in inhibiting the binding of [H-3]PK 11195. They all act as antagonists at central BZR. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.042
• 作为产物：
  描述：

  5-硝基吲哚 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 二苯醚 、 乙醇 、 丙酮 为溶剂， 反应 0.5h， 生成 3-ethyl-9-oxo-6,9-dihydro-3H-pyrrolo[3,2-f]quinoline-8-carboxylic acid ethyl ester
  参考文献：
  名称：

  Novel anellated pyrazoloquinolin-3-ones: synthesis and in vitro BZR activity

  摘要：

  A series of pyrazolo [4,3-c]pyrrolo[3,2-f]quinolin-3-one derivatives 6, 7a-c, 8a,b, 9a,b and 10-12 were synthesized as modified pyrazoloquinolinone analogs (PQs) and evaluated for their ability to inhibit radioligand to central and peripheral benzodiazepine receptors (BZRs) and their effect on GABA(A) α(1)β(2)γ(2L) receptors expressed in Xenopus laevis oocytes. Multistep synthesis starting from 5-nitroindole, via the Gould-Jacobs reaction to the quinoline nucleus, yielded key intermediates 9-chloro-3H-pyrrolo[3,2-f]quinoline-8-carboxylates. The reaction of the latter with methyl-hydrazine and various phenyl-hydrazines furnished the final compounds. In order to confirm the expected tetracyclic 2-substituted-2H-pyrazolopyrroloquinolin-3-one structure, IR spectrophotometric, mono-H-1 and C-13 and bi-dimensional spectrometric and HRMS analyses were carried out: all compounds were found to be 2-substituted 3-keto tautomers; compound 6 only differed because it turned out to be 1-methyl-2H-pyrazolo[4,3-c]pyrrolo[3,2-f]quinolin-3-olo. The results of this work are consistent with those previously reported for PQs: 7-9 show high potency in displacing specific [H-3]flunitrazepam from its receptor site; no compound was active in inhibiting the binding of [H-3]PK 11195. They all act as antagonists at central BZR. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.042