3H-9-氯吡咯并[3,2-F]喹啉 | 288570-10-5

• 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: 3H-9-氯吡咯并[3,2-F]喹啉
• 英文名称: 9-chloro-3H-pyrrolo[3,2-f]quinoline
• CAS: 288570-10-5
• 化学式: C₁₁H₇ClN₂
• 分子量: 202.643
• InChiKey: IDPPUDFSGNNPCV-UHFFFAOYSA-N

物化性质

• 沸点：
  402.0±25.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.68
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3H-9-氯吡咯并[3,2-F]喹啉 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以81%的产率得到3H-吡咯并[3,2-f]喹啉
  参考文献：
  名称：

  新型吡咯并[3,2-f]喹啉：合成和抗增殖活性。

  摘要：

  新型吡咯并[3,2，f]喹啉衍生物已被合成并作为抗增殖剂进行了测试。它们的特征是有角芳族三环系统，甲基可以在7位键合，并且具有甲磺酰胺侧链本身，或在1位缺少间甲氧基取代基。新化合物显示出当针对细胞系的NCI组，特别是那些从白血病获得的NCI组进行测试时，它们具有抑制细胞生长的特性。尽管这些化合物能够在高浓度下刺激拓扑异构酶II中毒，但细胞生长抑制特性似乎并不主要依赖于这种作用机理。总体而言，最有活性的化合物是化合物9，具有典型的氨色林的间甲氧基取代基，

  DOI：

  10.1016/s0968-0896(01)00071-2
• 作为产物：
  描述：

  5-硝基吲哚 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 三氯氧磷 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 12.83h， 生成 3H-9-氯吡咯并[3,2-F]喹啉
  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

• Synthesis and antiproliferative activity of some new DNA-targeted alkylating pyrroloquinolines
  作者：M Ferlin

  DOI：10.1016/j.bmc.2003.10.057

  日期：2004.2.15

  linked to an angular 3H-pyrrolo[3,2-f]quinoline nucleus, were synthetized and assayed for their in vitro antiproliferative activity. Simple convergent synthesis, consisting of separate preparation of 9-chloro-3H-pyrrolo[3,2-f]quinoline and p-amino-aniline derivatives, and following their linkage by substitution reactions 8a, b and 10, yielded the corresponding diol derivatives 7b and 9. Biological

  合成了两种新颖的直接DNA烷基化试剂，它们由与角状3H-吡咯并[3,2-f]喹啉核连接的苯胺芥菜组成，并对其体外抗增殖活性进行了测定。简单的收敛合成，包括分别制备9-氯代3H-吡咯并[3,2-f]喹啉和对氨基苯胺衍生物，并通过取代反应8a，b和10进行连接，得到相应的二醇衍生物评估了7b和9b的生物学特性，包括细胞生长抑制，与DNA形成交联的能力以及与大分子形成分子复合物的能力，涉及7b，8b，9和10。
• Mannich bases of 3H-pyrrolo[3,2-f]quinoline having vasorelaxing activity
  作者：Maria Grazia Ferlin、Gianfranco Chiarelotto、Francesca Antonucci、Laura Caparrotta、Guglielmina Froldi

  DOI：10.1016/s0223-5234(02)01355-7

  日期：2002.5

  Mannich bases obtained by aminoalkylation of 3H-pyrrolo[3,2-f]quinoline were designed and prepared as potential vasorelaxing agents. Compounds Ia-Va were characterised by IR, H-1-NMR, mass spectral data and elemental analysis; IIb,c-Vb,c were also confirmed by H-1-NMR spectra of reaction mixtures. To estimate their vascular activity, prototypes 1-(N,N-dimethylaminomethyl)- (Ia) and 1-(4-phenyl-piperazin-1-ylmethyl)- (IVa) 3H-pyrrolo[3,2-f]quinoline derivatives were studied in rat-tail arteries. In tissues precontracted with 0.5 muM 5-hydroxytryptamine (5-HT), 3 muM phenylephrine or 80 mM KCl, Ia and IVa showed endothelium-independent relaxing action. In a preliminary study on the cellular mechanisms of la, the influence of propranolol, a beta-receptor antagonist, and ketanserin, a 5-HT2A-receptor antagonist, was checked. In the presence of phenylephrine, the vasorclaxing effect of Ia was not affected by these inhibitors. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.
• DNA-targeting pyrroloquinoline-linked butenone and chalcones: Synthesis and biological evaluation
  作者：Lisa Dalla Via、Ornella Gia、Gianfranco Chiarelotto、Maria Grazia Ferlin

  DOI：10.1016/j.ejmech.2008.12.011

  日期：2009.7

  A series of conjugates of alpha,beta-unsaturated ketone systems, phenyl-butenone and diaryl-propenones (chalcones), with the tricyclic planar pyrroloquinoline nucleus were synthesised and evaluated for their anticancer properties. The aim was to target DNA by butenone and chalcones, and determine the occurrence of interactions with the macromolecule or related functional enzymes. The ability to inhibit cell growth was assayed on three human tumor cell lines, and the capacity to form molecular complexes with DNA was studied by linear flow dichroism (LD). The effect on the activity of the nuclear enzyme DNA topoisomerase II was also investigated.A noticeable cytotoxic effect was observed for all pyrroloquinoline-conjugated compounds 5 and 7a-c, particularly against human melanoma cell line JR8 (IC50 1.2-3.3 mu M); the unconjugated chalcones (8a-c) and butenone had a lower or no effect at the tested concentrations. LD experiments confirmed the pyrroloquinoline nucleus as an efficacious carrier for intercalative complexation with DNA. The ability of pyrroloquinoline derivatives to intercalate between base pairs appears to inhibit the relaxation of supercoiled DNA by topoisomerase II, while they induce no significant DNA cleavage. Since the concentrations inhibiting the enzyme appear relatively high with respect to cytotoxicity, the effective intercalation could affect the activity of more DNA processing enzymes and these overall nuclear effects may induce cell death. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Discovery of a new anilino-3H-pyrrolo[3,2-f]quinoline derivative as potential anti-cancer agent
  作者：L. Dalla Via、O. Gia、V. Gasparotto、M.G. Ferlin

  DOI：10.1016/j.ejmech.2007.04.008

  日期：2008.2

  The newly synthesized 1-[4-3H-pyrrolo[3,2-f]quinolin-9-ylamino)-phenyl]-ethanone hydrochloride showed high antiproliferative activity by mixed mechanisms of action. The compound acts by forming an intercalative complex with DNA and inhibiting DNA topoisomerase II (topo II) and by blocking the cell cycle in G(2)/M phase. Probable cell death by apoptosis is also suggested by flow cytometry analysis. (c) 2007 Elsevier Masson SAS. All rights reserved.