3,4-dihydro-2H-1-thia-4,5-diaza-anthraquinone | 1228299-90-8

• 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: 3,4-dihydro-2H-1-thia-4,5-diaza-anthraquinone
• 英文别名: 3,4-dihydro-2H-pyrido[2,3-g][1,4]benzothiazine-5,10-dione
• CAS: 1228299-90-8
• 化学式: C₁₁H₈N₂O₂S
• 分子量: 232.263
• InChiKey: KKMVVCFIHLSNSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-chloro-7-(2-chloro-ethylamino)-5,8-quinolinequinone 在 sodiumsulfide nonahydrate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以76%的产率得到3,4-dihydro-2H-1-thia-4,5-diaza-anthraquinone
  参考文献：
  名称：

  The anti-cancer, anti-inflammatory and tuberculostatic activities of a series of 6,7-substituted-5,8-quinolinequinones

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.03.021

文献信息

• [EN] INHIBITORS OF CANCER STEM CELLS<br/>[FR] INHIBITEURS DE CELLULES SOUCHES CANCÉREUSES
  申请人：UNIV PITTSBURGH

  公开号：WO2011130677A1

  公开（公告）日：2011-10-20

  A method of treating cancer in a subject, comprising co-administering to the subject (a) a therapeutically effective amount of at least one compound that selectively targets cancer stem cells, wherein the compound is selected from an indenoisoquinoline compound, a naphthoquinone compound, a quinolinedione compound, bouvardin, A-77636, rottlerin, or CGP-74514A, or a pharmaceutically acceptable salt or ester thereof, and (b) a therapeutically effective amount of at least one anti-cancer agent.
• 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.