9-羟基-3H-吡咯并[3,2-f]喹啉-8-羧酸乙酯 | 853068-82-3

• 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
• 中文名称: 9-羟基-3H-吡咯并[3,2-f]喹啉-8-羧酸乙酯
• 英文名称: Ethyl 9-oxo-6,9-dihydro-3H-pyrrolo[3,2-f]quinoline-8-carboxylate
• 英文别名: ethyl 9-oxo-3,6-dihydropyrrolo[3,2-f]quinoline-8-carboxylate
• CAS: 853068-82-3；39487-15-5
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: ZZQCHMVODPWDGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-羟基-3H-吡咯并[3,2-f]喹啉-8-羧酸乙酯 在 盐酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二苯醚 为溶剂， 反应 3.33h， 生成 3H-9-(o-methoxy-p-methanesulfonamido-aniline)-pyrrolo[3,2-f]quinoline
  参考文献：
  名称：

  Pyrrolo-quinoline derivatives as potential antineoplastic drugs

  摘要：

  Some novel pyrrolo-quinoline derivatives have been synthesized as potential antineoplastic agents. They contain an angular aromatic tricyclic or tetracyclic system, to which the methanesulfon-anisidide side chain typical of amsacrine as such, or lacking the m-methoxy substituent, is connected. A methyl group can be present at position 7 of the pyrrolo-quinoline ring. The novel compounds exhibit interesting cell growth inhibitory properties when tested against the NCI panel of cell lines, in particular those obtained from solid tumors like CNS-, melanoma- and prostate-derived cells. The mechanism of cytotoxic action does not seem to be related to topoisomerase II poisoning ability. Most active proved to be compound 4a, which lacks both methyl and methoxy substituents, followed by 5a, having the methoxy group only. Biological activity is less pronounced in the tetracyclic family of derivatives 6 and 7. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00060-2
• 作为产物：
  描述：

  5-硝基吲哚 在 palladium on activated charcoal 氢气 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 9.5h， 生成 9-羟基-3H-吡咯并[3,2-f]喹啉-8-羧酸乙酯
  参考文献：
  名称：

  Pyrrolo-quinoline derivatives as potential antineoplastic drugs

  摘要：

  Some novel pyrrolo-quinoline derivatives have been synthesized as potential antineoplastic agents. They contain an angular aromatic tricyclic or tetracyclic system, to which the methanesulfon-anisidide side chain typical of amsacrine as such, or lacking the m-methoxy substituent, is connected. A methyl group can be present at position 7 of the pyrrolo-quinoline ring. The novel compounds exhibit interesting cell growth inhibitory properties when tested against the NCI panel of cell lines, in particular those obtained from solid tumors like CNS-, melanoma- and prostate-derived cells. The mechanism of cytotoxic action does not seem to be related to topoisomerase II poisoning ability. Most active proved to be compound 4a, which lacks both methyl and methoxy substituents, followed by 5a, having the methoxy group only. Biological activity is less pronounced in the tetracyclic family of derivatives 6 and 7. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00060-2

文献信息

• Novel anellated pyrazoloquinolin-3-ones: synthesis and in vitro BZR activity
  作者：Maria Grazia Ferlin、Gianfranco Chiarelotto、Stefano Dall’Acqua、Elisabetta Maciocco、Maria Paola Mascia、Maria Giuseppina Pisu、Giovanni Biggio

  DOI：10.1016/j.bmc.2005.02.042

  日期：2005.5

  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.