3-(2-(3-chloro-2-methylphenyl)hydrazono)-7-nitroquinoline-2,4 (1H,3H)-dione | 1331969-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(2-(3-chloro-2-methylphenyl)hydrazono)-7-nitroquinoline-2,4 (1H,3H)-dione
• 英文别名: 3-[(3-chloro-2-methylphenyl)hydrazinylidene]-7-nitro-1H-quinoline-2,4-dione
• CAS: 1331969-84-6
• 化学式: C₁₆H₁₁ClN₄O₄
• 分子量: 358.741
• InChiKey: ZVZARABUIKULKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  113.7
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-hydroxy-7-nitro-2(1H)-quinolinone 、 3-氯-2-甲基苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 以49%的产率得到3-(2-(3-chloro-2-methylphenyl)hydrazono)-7-nitroquinoline-2,4 (1H,3H)-dione
  参考文献：
  名称：

  Diversity oriented design of various hydrazides and their in vitro evaluation against Mycobacterium tuberculosis H37Rv strains

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.06.074

文献信息

• 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.