5,8-喹啉二酮,6,7-二(苯基硫代)- | 102183-15-3

• 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
• 中文名称: 5,8-喹啉二酮,6,7-二(苯基硫代)-
• 英文名称: 6,7-bis(phenylthio)quinoline-5,8-dione
• 英文别名: 6,7-bis-phenylsulfanyl-5,8-quinolinequinone；6,7-bis-phenylsulfanyl-quinoline-5,8-dione；6,7-Bis-phenylmercapto-chinolin-5,8-dion；5,8-Quinolinedione, 6,7-bis(phenylthio)-；6,7-bis(phenylsulfanyl)quinoline-5,8-dione
• CAS: 102183-15-3
• 化学式: C₂₁H₁₃NO₂S₂
• 分子量: 375.472
• InChiKey: GQMQXCVRWWTFLN-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178 °C (decomp)
• 沸点：
  532.7±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,8-喹啉二酮 在 乙醇 、 水 、 三氯化铁 作用下， 生成 5,8-喹啉二酮,6,7-二(苯基硫代)-
  参考文献：
  名称：

  Die Darstellung von Arylmercapto-hydroxy-chinolinen

  摘要：

  DOI：

  10.1002/ardp.19582910909

文献信息

• The anti-cancer, anti-inflammatory and tuberculostatic activities of a series of 6,7-substituted-5,8-quinolinequinones
  作者：Benjamin J. Mulchin、Christopher G. Newton、James W. Baty、Carole H. Grasso、William John Martin、Michaela C. Walton、Emma M. Dangerfield、Catherine H. Plunkett、Michael V. Berridge、Jacquie L. Harper、Mattie S.M. Timmer、Bridget L. Stocker

  DOI：10.1016/j.bmc.2010.03.021

  日期：2010.5

  A variety of 6,7-substituted-5,8-quinolinequinones were synthesised and assessed for their anti-tumour and anti-inflammatory activities, and their ability to inhibit the growth of Mycobacterium bovis BCG. In particular, the introduction of a sulfur group at the 7-position of the quinolinequinone led to the discovery of two compounds, 6-methylamino-7-methylsulfanyl-5,8-quinolinequinone (10a) and 6-amino-7-methylsulfonyl-5,8-quinolinequinone ( 12), that exhibited selectivity for leukemic cells over T-cells, a highly desirable property for an anti-cancer drug. A number of anti-inflammatory ( AI) compounds were also identified, with 6,7-bis-methylsulfanyl-5,8-quinolinequinone (18a) exhibiting the highest AI activity (0.11 mu M), while 6,7-dichloro-5,8-quinolinequinone (7a), 6,7-dichloro-2-methyl-5,8-quinolinequinone (7b), and 6,7-bis-phenylsulfanyl-quinoline-5,8-diol ( 19) also exhibited good AI activity and specificity. Several quinolinequinone TB-drug candidates were identified. Of these, 6-amino-7-chloro-5,8-quinolinequinone ( 11) and 6-amino-7-methanesulfinyl-5,8-quinolinequinone ( 14), exhibited low MICs (1.56-3.13 mu g/mL) for the 100% growth inhibition of M. Bovis BCG. Some general trends pertaining to the functional group substitution of the quinolinequinone core and biological activity were also identified. (C) 2010 Elsevier Ltd. All rights reserved.
• Die Darstellung von Arylmercapto-hydroxy-chinolinen
  作者：Helmut Zinner、Heinz Fiedler

  DOI：10.1002/ardp.19582910909

  日期：——
• An efficient method for the synthesis of 6,7-bis(alkylthio- or alkylamino-substituted)quinoline-5,8-diones via nucleophilic addition/oxidation of alkylthio and alkylamino derivatives to quinoline-5,8-dione
  作者：Herman H. Odens、Trevor S. Silva、Candace N. Olusola、Herman H. Odens、Victoria A. Howe、Anna I. Wijatyk

  DOI：10.24820/ark.5550190.p011.428

  日期：——