6-chloro-2-fluoro-11H-indolo[3,2-c]quinoline | 1198086-27-9

• 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: 6-chloro-2-fluoro-11H-indolo[3,2-c]quinoline
• CAS: 1198086-27-9
• 化学式: C₁₅H₈ClFN₂
• 分子量: 270.693
• InChiKey: VJHYSDWESFJZMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-2-fluoro-11H-indolo[3,2-c]quinoline 以 四氢呋喃 为溶剂， 生成 1-(3-(2-fluoro-11H-indolo[3,2-c]quinolin-6-ylamino)propyl)-3-phenylurea
  参考文献：
  名称：

  Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11

  摘要：

  A series of indolo[3,2-c]quinolines were synthesized by modifying the side chains of the omega-aminoalkylamines at the C6 position and introducing substituents at the C2 position, such as F, Cl, Br, Me, MeO and NO2, and a methyl group at the N11 position for an SAR study. The in vitro antiplasmodial activities of the derivative agents against two different strains (CQS: NF54 and CQR: K1) and the cytotoxic activity against normal L6 cells were evaluated. The test results showed that compounds 6k and 6l containing the branched methyl groups of 3-aminopropylamino at C6 with a Cl atom at C2 exhibited a very low cytotoxicity with IC50 values above 4000 nM, high antimalarial activities with IC50 values of about 11 nM for CQS (NF54), IC50 values of about 17 nM for CQR (K1), and RI resistance indices of 1.6. Furthermore, the compounds were tested for beta-haematic inhibition, and QSAR revealed an interesting linear correlation between the biological activity of CQS (NF54) and three contributing factors, namely solubility, hydrophilic surface area, and beta-haematin inhibition for this series. In vivo testing of 6l showed a reduction in parasitaemia on day 4 with an activity of 38%. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.030
• 作为产物：
  描述：

  2-氨基苄胺 在 溶剂黄146 、 三氯氧磷 作用下， 反应 4.0h， 生成 6-chloro-2-fluoro-11H-indolo[3,2-c]quinoline
  参考文献：
  名称：

  Ruthenium− and Osmium−Arene Complexes of 2-Substituted Indolo[3,2-c]quinolines: Synthesis, Structure, Spectroscopic Properties, and Antiproliferative Activity

  摘要：

  The synthesis of new modified indolo[3,2-c]quinoline ligands L-1-L-8 with metal-binding sites is reported. By coordination to ruthenium- and osmium-arene moieties 16 complexes of the type [(eta(6)-p-cymene)M(L)Cl]Cl (1a,b-8a,b), where M is Ru-II or Os-II and L is L-1-L-8, have been prepared. All compounds were comprehensively characterized by elemental analysis, electrospray ionization mass spectrometry, IR, UV-vis, and NMR spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction (2a, 4a, 4b, 5a, 7a, and 7b). The complexes were tested for antiproliferative activity in vitro in three human cancer cell lines, namely, CH1 (ovarian carcinoma), SW480 (colon adenocarcinoma), and A549 (non-small-cell lung cancer), yielding IC50 values in the submicromolar or low micromolar range.

  DOI：

  10.1021/om101004z

文献信息

• Synthesis and antiproliferative evaluation of certain indolo[3,2-c]quinoline derivatives
  作者：Chih-Ming Lu、Yeh-Long Chen、Hui-Ling Chen、Chyi-An Chen、Pei-Jung Lu、Chia-Ning Yang、Cherng-Chyi Tzeng

  DOI：10.1016/j.bmc.2010.01.033

  日期：2010.3

  The present report describes the synthesis and antiproliferative evaluation of certain indolo[3,2-c]quinoline derivatives. For the C6 anilino-substituted derivatives, (11H-indolo[3,2-c]quinolin-6-yl)phenylamine (6a) was inactive. Structural optimization of 6a by the introduction of a hydroxyl group at the anilino-moiety resulted in the enhancement of antiproliferative activity in which the activity

  本报告描述了某些吲哚并[3,2- c ]喹啉衍生物的合成和抗增殖评价。对于C 6苯胺基取代的衍生物，（11 H-吲哚并[3，2 - c ]喹啉-6-基）苯胺（6a）是不活泼的。通过在苯胺基部分引入羟基来优化6a的结构导致抗增殖活性增强，其中活性按对-OH，7a  > 间位-OH，8a  > 邻位-OH，9a的顺序降低。对于C 6烷基氨基取代的衍生物11a，12a，13a，14a和15a对所有测试的癌细胞和底特律551皮肤正常成纤维细胞均表现出相当的抗增殖活性。HeLa，A549和SKHep这三种癌细胞非常敏感，IC 50小于2.17μM，而PC-3对这组吲哚[3,2- c ]喹啉具有相对抗性。对于-2-苯乙氨基衍生物，化合物20A是对HeLa细胞的具有IC的生长活性50 0.52μM的，但是对活塞551的与IC生长不太有效50为19.32μM。对于双吲哚并[3,2- Ç〕喹啉，Ñ，ñ -双-
• Indolo[3,2-c]quinoline Compounds
  申请人：TZENG CHERNG-CHYI

  公开号：US20090298846A1

  公开（公告）日：2009-12-03

  Indolo[3,2-c]quinoline compounds of formula (I) shown below. Each variable in this formula is defined herein. These compounds can be used to inhibit both growth of cancer cells and activity of telomerase.

  下面是化学式为(I)的Indolo[3,2-c]喹啉化合物。该式中的每个变量在此处有定义。这些化合物可用于抑制癌细胞的生长和端粒酶的活性。
• Ruthenium− and Osmium−Arene Complexes of 2-Substituted Indolo[3,2-<i>c</i>]quinolines: Synthesis, Structure, Spectroscopic Properties, and Antiproliferative Activity
  作者：Lukas K. Filak、Gerhard Mühlgassner、Felix Bacher、Alexander Roller、Mathea Sophia Galanski、Michael A. Jakupec、Bernhard K. Keppler、Vladimir B. Arion

  DOI：10.1021/om101004z

  日期：2011.1.24

  The synthesis of new modified indolo[3,2-c]quinoline ligands L-1-L-8 with metal-binding sites is reported. By coordination to ruthenium- and osmium-arene moieties 16 complexes of the type [(eta(6)-p-cymene)M(L)Cl]Cl (1a,b-8a,b), where M is Ru-II or Os-II and L is L-1-L-8, have been prepared. All compounds were comprehensively characterized by elemental analysis, electrospray ionization mass spectrometry, IR, UV-vis, and NMR spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction (2a, 4a, 4b, 5a, 7a, and 7b). The complexes were tested for antiproliferative activity in vitro in three human cancer cell lines, namely, CH1 (ovarian carcinoma), SW480 (colon adenocarcinoma), and A549 (non-small-cell lung cancer), yielding IC50 values in the submicromolar or low micromolar range.
• US7763633B2
  申请人：——

  公开号：US7763633B2

  公开（公告）日：2010-07-27
• Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11
  作者：Ning Wang、Kathryn J. Wicht、Kento Imai、Ming-qi Wang、Tran Anh Ngoc、Ryo Kiguchi、Marcel Kaiser、Timothy J. Egan、Tsutomu Inokuchi

  DOI：10.1016/j.bmc.2014.03.030

  日期：2014.5

  A series of indolo[3,2-c]quinolines were synthesized by modifying the side chains of the omega-aminoalkylamines at the C6 position and introducing substituents at the C2 position, such as F, Cl, Br, Me, MeO and NO2, and a methyl group at the N11 position for an SAR study. The in vitro antiplasmodial activities of the derivative agents against two different strains (CQS: NF54 and CQR: K1) and the cytotoxic activity against normal L6 cells were evaluated. The test results showed that compounds 6k and 6l containing the branched methyl groups of 3-aminopropylamino at C6 with a Cl atom at C2 exhibited a very low cytotoxicity with IC50 values above 4000 nM, high antimalarial activities with IC50 values of about 11 nM for CQS (NF54), IC50 values of about 17 nM for CQR (K1), and RI resistance indices of 1.6. Furthermore, the compounds were tested for beta-haematic inhibition, and QSAR revealed an interesting linear correlation between the biological activity of CQS (NF54) and three contributing factors, namely solubility, hydrophilic surface area, and beta-haematin inhibition for this series. In vivo testing of 6l showed a reduction in parasitaemia on day 4 with an activity of 38%. (C) 2014 Elsevier Ltd. All rights reserved.