3-bromo-11H-indolo<3,2-c>quinoline | 155249-44-8

• 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-bromo-11H-indolo<3,2-c>quinoline
• 英文别名: 3-Bromo-11H-indolo[3,2-c]quinoline
• CAS: 155249-44-8
• 化学式: C₁₅H₉BrN₂
• 分子量: 297.154
• InChiKey: AXXJRLKZJHCKNA-UHFFFAOYSA-N

物化性质

• 沸点：
  518.6±30.0 °C(Predicted)
• 密度：
  1.655±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 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：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-11H-indolo<3,2-c>quinoline 在 sodium hydroxide 、 苄基三乙基氯化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.67h， 生成 2-(3-bromo-5-oxidoindolo[3,2-c]quinolin-5-ium-11-yl)-N,N-diethylethanamine oxide
  参考文献：
  名称：

  Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]

  摘要：

  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.

  DOI：

  10.1016/0223-5234(93)90036-e
• 作为产物：
  描述：

  3-((N-(3-bromophenyl)-4-methylphenyl)sulfonamido)propanoic acid 在 盐酸 、 三氯化铝 、 五氯化磷 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 24.5h， 生成 3-bromo-11H-indolo<3,2-c>quinoline
  参考文献：
  名称：

  Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]

  摘要：

  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.

  DOI：

  10.1016/0223-5234(93)90036-e

文献信息

• Scaffold and Parasite Hopping: Discovery of New Protozoal Proliferation Inhibitors
  作者：Baljinder Singh、Jean A. Bernatchez、Laura-Isobel McCall、Claudia M. Calvet、Jasmin Ackermann、Julia M. Souza、Diane Thomas、Everton M. Silva、Kelly A. Bachovchin、Dana M. Klug、Hitesh B. Jalani、Seema Bag、Melissa J. Buskes、Susan E. Leed、Norma E. Roncal、Erica C. Penn、Jessey Erath、Ana Rodriguez、Richard J. Sciotti、Robert F. Campbell、James McKerrow、Jair L. Siqueira-Neto、Lori Ferrins、Michael P. Pollastri

  DOI：10.1021/acsmedchemlett.9b00453

  日期：2020.3.12

  approach, we tested a previously reported library of compounds that were active against Trypanosoma brucei, plus 31 new compounds, against a variety of protozoan parasites including Trypanosoma cruzi, Leishmania major, Leishmania donovani, and Plasmodium falciparum. This led to the discovery of several compounds with submicromolar activities and improved physicochemical properties that are early leads

  利用目标再利用和寄生虫跳跃方法，我们测试了先前报道的化合物库，这些化合物库对布氏锥虫具有活性，外加 31 种新化合物，可对抗各种原生动物寄生虫，包括克氏锥虫、主要利什曼原虫、多诺瓦尼利什曼原虫和恶性疟原虫。这导致发现了几种具有亚微摩尔活性和改善物理化学性质的化合物，这些化合物是开发针对动质体疾病和疟疾的化学治疗剂的早期线索。
• 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：——
• 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.