6-Bromo-4-hydroxyquinoline-3-carbohydrazide | 1462359-41-6

• 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-Bromo-4-hydroxyquinoline-3-carbohydrazide
• 英文别名: 6-bromo-4-oxo-1H-quinoline-3-carbohydrazide
• CAS: 1462359-41-6；874792-18-4
• 化学式: C₁₀H₈BrN₃O₂
• 分子量: 282.096
• InChiKey: HWOPDVQLXVYZSB-UHFFFAOYSA-N

物化性质

• 密度：
  1.725±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Bromo-4-hydroxyquinoline-3-carbohydrazide 、 水杨醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以94%的产率得到
  参考文献：
  名称：

  Quinolone-N-acylhydrazone hybrids as potent Zika and Chikungunya virus inhibitors

  摘要：

  This work reports the synthesis of quinolone-N-acylhydrazone hybrids, namely 6-R-N'-(2 hydxoxybenzylidene)-4-oxo-1,4-dihydroquinoline-3-carbohydrazide (R = H: 5a, F: 5b, Cl: 5c and Br: 5d), which exhibited excellent activity against arbovirus Zika (ZIKV) and Chikungunya (CHIKV). In vitro screening towards ZIKV and CHIKV inhibition revealed that all substances have significant antiviral activity, most of them being more potent than standard Ribavirin (5a-d: EC50 = 0.75-0.81 mu M, Ribavirin: EC50 = 3.95 mu M for ZIKV and 5a-d: 1.16-2.85 mu M, Ribavirin: EC50 = 2.42 mu M for CHIKV). The quinolone-N-acylhydrazone hybrids were non-toxic against Vero cells, in which compounds 5c and 5d showed the best selectivities (SI = 1410 and 630 against ZIKV and CHIKV, respectively). Antiviral activity was identified by inhibition of viral RNA production in a dose-dependent manner. In the evaluation of the time of addition of the compounds, we observed that 5b and 5c remain with strong effect even in the addition for 12 h after infection. The above results indicate that quinolone-N-acylhydrazones represent a new and promising class to be further investigated as anti-ZIKV and anti-CHIKV agents.

  DOI：

  10.1016/j.bmcl.2019.126881
• 作为产物：
  描述：

  (4-溴苯胺亚甲基)丙二酸二乙酯 在 一水合肼 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 5.5h， 生成 6-Bromo-4-hydroxyquinoline-3-carbohydrazide
  参考文献：
  名称：

  取代的-4-oxo-1，4-dihydro-3- [1-oxo-2-hydrazino-3- {ptoluenesulfon}]喹啉衍生物的合成及其对细菌感染的生物学活性

  摘要：

  我们已经合成了一系列被对甲苯磺酰基取代的喹诺酮和氟喹诺酮类衍生物。筛选所有这些化合物作为抗菌剂，并将其数据与市场上出售的参比药物进行比较。环丙沙星和诺氟沙星。

  DOI：

  10.13005/ojc/290216

文献信息

• Synthesis of substituted-4-oxo-1, 4-dihydro-3-[1-oxo-2-hydrazino-3-{ptoluenesulfon}] quinoline Derivatives and their Biological Activity Against Bacterial Infections
  作者：N. SRIVATAVA、A. KUMAR

  DOI：10.13005/ojc/290216

  日期：2013.6.30

  We have synthesized a series of quinolone and fluoroquinolones derivatives substituted with p-tosyl group. All these compounds were screened as antibacterial and datas were compared with reference marketed drug viz.; Ciprofloxacin & Norfloxacin.

  我们已经合成了一系列被对甲苯磺酰基取代的喹诺酮和氟喹诺酮类衍生物。筛选所有这些化合物作为抗菌剂，并将其数据与市场上出售的参比药物进行比较。环丙沙星和诺氟沙星。
• Quinolone-N-acylhydrazone hybrids as potent Zika and Chikungunya virus inhibitors
  作者：Roberta K.F. Marra、Arthur E. Kümmerle、Guilherme P. Guedes、Caroline de S. Barros、Rafaela S.P. Gomes、Claudio C. Cirne-Santos、Izabel Christina N.P. Paixão、Amanda P. Neves

  DOI：10.1016/j.bmcl.2019.126881

  日期：2020.1

  This work reports the synthesis of quinolone-N-acylhydrazone hybrids, namely 6-R-N'-(2 hydxoxybenzylidene)-4-oxo-1,4-dihydroquinoline-3-carbohydrazide (R = H: 5a, F: 5b, Cl: 5c and Br: 5d), which exhibited excellent activity against arbovirus Zika (ZIKV) and Chikungunya (CHIKV). In vitro screening towards ZIKV and CHIKV inhibition revealed that all substances have significant antiviral activity, most of them being more potent than standard Ribavirin (5a-d: EC50 = 0.75-0.81 mu M, Ribavirin: EC50 = 3.95 mu M for ZIKV and 5a-d: 1.16-2.85 mu M, Ribavirin: EC50 = 2.42 mu M for CHIKV). The quinolone-N-acylhydrazone hybrids were non-toxic against Vero cells, in which compounds 5c and 5d showed the best selectivities (SI = 1410 and 630 against ZIKV and CHIKV, respectively). Antiviral activity was identified by inhibition of viral RNA production in a dose-dependent manner. In the evaluation of the time of addition of the compounds, we observed that 5b and 5c remain with strong effect even in the addition for 12 h after infection. The above results indicate that quinolone-N-acylhydrazones represent a new and promising class to be further investigated as anti-ZIKV and anti-CHIKV agents.