7,8-Dichloro-4-hydroxyquinolin-2(1H)-one | 1331970-41-2

• 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: 7,8-Dichloro-4-hydroxyquinolin-2(1H)-one
• 英文别名: 7,8-dichloro-4-hydroxy-1H-quinolin-2-one
• CAS: 1331970-41-2
• 化学式: C₉H₅Cl₂NO₂
• 分子量: 230.05
• InChiKey: HMMXGPYSWYXNNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  444.2±45.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7,8-Dichloro-4-hydroxyquinolin-2(1H)-one 、 3-甲基苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.5h， 以47%的产率得到7,8-dichloro-3-[2-(m-tolyl)hydrazono]quinoline-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and binary QSAR study of antitubercular quinolylhydrazides

  摘要：

  In continuation with our previous work in anti-TB research area, in the present study we have demonstrated the structural diversity of quinolylhydrazides as potent anti-tuberculars. The compound library was synthesized by molecular hybridization approach and tested in vitro against Mycobacterium tuberculosis H(37)Rv strains. Among the designed conjugates, the most promising molecules were found to exhibit 100% Growth Inhibition (GI) at MIC <6.25 mu g/mL. Moreover, several analogs in the designed series were also turned out as excellent anti-tuberculars. To probe the structural characteristics influencing on the SAR, the classification model was generated using a binary QSAR approach termed recursive partitioning (RP) analysis. The significant features outlined by the RP model act as a guide in order to design the 'lead' compound. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.076

文献信息

• Isoindolinpigmente, Verfahren zu deren Herstellung und Verwendung
  申请人：CIBA-GEIGY AG

  公开号：EP0029007A1

  公开（公告）日：1981-05-20

  Isoindolinpigmente der Formel worin R einen Alkylrest mit 1-4 C, der durch eine Hydroxy-, Cyan-, Phenyl- oder Carbamoylgruppe eine Alkoxygruppe mit 1-4 C, eine Aryloxy-, Aryloxycarbonyl-, Aroyloxy- oder Aroylaminogruppe eine Alkoxycarbonyl-, Alkanoyloxy-, Alkylcarbamoyl- oder Alkanoylaminogruppe mit 2-6 C oder eine Phthalimidogruppe substituiert sein kann, oder eine Cycloalkylgruppe mit 5-8 C und X einen Rest der Formel bedeutet, worin Y und Z für H oder Halogenatome, Alkyl- oder Alkoxygruppen mit 1 - 4 C bedeuten. Diese Pigmente eignen sich zum Färben hochmolekularer organischer Verbindungen und zeichen sich durch Reinheit des Farbtones, gute Licht-, Wetter-, Migrations-, Ueberlackier- und Lösungsmittelechtheit sowie Hitzebeständigkeit aus.

  式中的异吲哚啉颜料 其中 R 是具有 1-4 C 的烷基，可被羟基、氰基、苯基或氨基甲酰基、具有 1-4 C 的烷氧基、芳氧基、芳氧羰基、芳氧基或芳基氨基、具有 2-6 C 的烷氧羰基、烷酰氧基、烷基氨基甲酰基或烷酰氨基或邻苯二甲酰亚胺基取代，或具有 2-6 C 的烷酰氧基、烷基氨基甲酰基或烷酰氨基或邻苯二甲酰亚胺基、具有 2-6 C 或邻苯二甲酰亚胺基的烷酰氧基、烷基氨基甲酰基或烷酰氨基，或具有 5-8 C 的环烷基，且 X 是式中的基团 其中 Y 和 Z 为 H 或卤素原子、1-4 C 的烷基或烷氧基。这些颜料适用于高分子有机化合物的着色，具有颜色纯正、耐光、耐候、耐迁移、耐过涂、耐溶剂和耐热等特点。
• Diversity oriented design of various hydrazides and their in vitro evaluation against Mycobacterium tuberculosis H37Rv strains
  作者：Atul Manvar、Abhay Bavishi、Ashish Radadiya、Jignesh Patel、Vipul Vora、Narshih Dodia、Kena Rawal、Anamik Shah

  DOI：10.1016/j.bmcl.2011.06.074

  日期：2011.8

  Control and prevention of tuberculosis is a major challenge, as one-third of the world's population is infected with Mycobacterium tuberculosis. The resurgence of tuberculosis and the emergence of multidrug-resistance strains of mycobacteria, necessitate the search for new class of antimycobacterial agents. As a part of investigation of new antitubercular agents in this laboratory, we describe the syntheses of various hydrazides of comarins, quinolones and pyrroles and screening against M. tuberculosis (Mtb) H37(Rv) by using rifampin as a standard drug. Among the designed molecules, the most prominent compounds 2a-g, 4a and 9a showed > 90% GI at MIC < 6.25 mu g/mL. Finally, these studies suggests that compounds 2a-g, 4a and 9a may serve as promising lead scaffolds for further generation of new anti-TB agents. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and binary QSAR study of antitubercular quinolylhydrazides
  作者：Atul Manvar、Vijay Khedkar、Jignesh Patel、Vipul Vora、Narsinh Dodia、Gautam Patel、Evans Coutinho、Anamik Shah

  DOI：10.1016/j.bmcl.2013.06.076

  日期：2013.9

  In continuation with our previous work in anti-TB research area, in the present study we have demonstrated the structural diversity of quinolylhydrazides as potent anti-tuberculars. The compound library was synthesized by molecular hybridization approach and tested in vitro against Mycobacterium tuberculosis H(37)Rv strains. Among the designed conjugates, the most promising molecules were found to exhibit 100% Growth Inhibition (GI) at MIC <6.25 mu g/mL. Moreover, several analogs in the designed series were also turned out as excellent anti-tuberculars. To probe the structural characteristics influencing on the SAR, the classification model was generated using a binary QSAR approach termed recursive partitioning (RP) analysis. The significant features outlined by the RP model act as a guide in order to design the 'lead' compound. (C) 2013 Elsevier Ltd. All rights reserved.