8-methoxy-11H-indolo[3,2-c]quinoline | 155249-83-5

• 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
• 英文名称: 8-methoxy-11H-indolo[3,2-c]quinoline
• CAS: 155249-83-5
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: HVJHHXNYMJFOJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methoxy-11H-indolo[3,2-c]quinoline 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 以89%的产率得到11H-Indolo[3,2-c]quinolin-8-ol
  参考文献：
  名称：

  Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern—synthesis and biological activity studies of 11H-indolo[3.2-c]quinoline derivatives

  摘要：

  Designed as a new group of planar molecule containing the proposed 2-phenylnaphthalene-type structure, a number of 11H-indolo[3.2-c]quinoline derivatives were synthesized and evaluated biologically. Several compounds were found to possess cytotoxic activity against the growth of human promyclocytic leukemia cells (HL-60), against the small cell lung cancer (SCLC), and showed good response in the National Cancer Institute preclinical antitumor drug discovery 60-cell line panel. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01420-4
• 作为产物：
  描述：

  4-氯喹啉 在 甲烷磺酸 、 palladium diacetate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 8-methoxy-11H-indolo[3,2-c]quinoline
  参考文献：
  名称：

  Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern—synthesis and biological activity studies of 11H-indolo[3.2-c]quinoline derivatives

  摘要：

  Designed as a new group of planar molecule containing the proposed 2-phenylnaphthalene-type structure, a number of 11H-indolo[3.2-c]quinoline derivatives were synthesized and evaluated biologically. Several compounds were found to possess cytotoxic activity against the growth of human promyclocytic leukemia cells (HL-60), against the small cell lung cancer (SCLC), and showed good response in the National Cancer Institute preclinical antitumor drug discovery 60-cell line panel. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01420-4

文献信息

• Auto-Tandem Catalysis: Synthesis of Substituted 11H-Indolo[3,2-c]quinolinesvia Palladium-Catalyzed Intermolecular CN and Intramolecular CC Bond Formation
  作者：Caroline Meyers、Geert Rombouts、Kristof T. J. Loones、Alberto Coelho、Bert U. W. Maes

  DOI：10.1002/adsc.200700328

  日期：2008.2.22

  D-Ring substituted 11H-indolo[3,2-c]quinolines (4) have been prepared via auto-tandem consecutive intermolecular Buchwald-Hartwig reaction and intramolecular palladium-catalyzed arylation on 4-chloroquinoline (1) with N-unsubstituted 2-chloroanilines (2). The reported 11H-indolo[3,2-c]quinolines (4) represent the first examples in which tandem catalysis has been used to construct N-unsubstituted carbolines

  D-Ring取代的11 H-吲哚并[3,2- c ]喹啉（4）是通过自动串联连续分子间Buchwald-Hartwig反应和分子内钯催化的4-氯喹啉（1）上的N-未取代的2芳基化反应制得的-氯苯胺（2）。报道的11 H-吲哚并[3,2- c ]喹啉（4）代表了第一个实例，其中串联催化已用于构建N-未取代的咔啉。
• Regiodivergent Synthesis of 11 <i>H</i> ‐Indolo[3,2‐ <i>c</i> ]quinolines and Neocryptolepine from a Common Starting Material
  作者：Katja S. Håheim、Bjarte Aarmo Lund、Magne O. Sydnes

  DOI：10.1002/ejoc.202300137

  日期：——

  A common intermediate gives easy access to both neocryptolepine and isocryptolepine analogues in up to 80 % and 95 % yield, respectively.

  一种常见的中间体可以很容易地以高达 80% 和 95% 的收率分别获得新隐藤碱和异隐藤碱类似物。
• Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]
  作者：LM Werbel、SJ Kesten、WR Turner

  DOI：10.1016/0223-5234(93)90036-e

  日期：1993.1

  Structure-activity relationships have been ascertained and chemical methodology developed for a series of antimalarial 3-chloroindolo[3,2-c]quinoline-5-oxides. The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3. Substitution at positions 7, 8, 9, 10 is not essential, although the most potent analog in our studies was the 8-nitro compound 4vv.
• Werbel L. M., Kesten S. J., Turner W. R., Eur. J. Med. Chem, 28 (1993) N 11, S 837-852
  作者：Werbel L. M., Kesten S. J., Turner W. R.

  DOI：——

  日期：——
• Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern—synthesis and biological activity studies of 11H-indolo[3.2-c]quinoline derivatives
  作者：L He

  DOI：10.1016/s0223-5234(02)01420-4

  日期：2003.1

  Designed as a new group of planar molecule containing the proposed 2-phenylnaphthalene-type structure, a number of 11H-indolo[3.2-c]quinoline derivatives were synthesized and evaluated biologically. Several compounds were found to possess cytotoxic activity against the growth of human promyclocytic leukemia cells (HL-60), against the small cell lung cancer (SCLC), and showed good response in the National Cancer Institute preclinical antitumor drug discovery 60-cell line panel. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.