7-chloro-6-methylamino-5,8-quinolinequinone | 35682-92-9

• 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-chloro-6-methylamino-5,8-quinolinequinone
• 英文别名: 7-chloro-6-methylamino-quinoline-5,8-dione；7-Chlor-6-methylamino-chinolin-5,8-dion；7-chloro-6-(methylamino)quinoline-5,8-dione
• CAS: 35682-92-9
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: HXCLSOIIZPDEEN-UHFFFAOYSA-N

物化性质

• 熔点：
  219.0-219.2 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  349.6±42.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-chloro-6-methylamino-5,8-quinolinequinone 、 苯硫酚 在 吡啶 作用下， 反应 16.0h， 以95%的产率得到6-methylamino-7-phenylsulfanyl-5,8-quinolinequinone
  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
• 作为产物：
  描述：

  6,7-二氯-5,8-喹啉二酮 、 甲胺 在 nickel(II) chloride hexahydrate 作用下， 以 乙醇 为溶剂， 反应 1.75h， 以95%的产率得到7-chloro-6-methylamino-5,8-quinolinequinone
  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

• Furoquinolinediones as inhibitors of TDP2
  申请人：An Linkun

  公开号：US10906914B2

  公开（公告）日：2021-02-02

  Compounds of Formula I and the pharmaceutically acceptable salts thereof are disclosed Formula I. The variables X1, X2, and R1-4 are disclosed herein. The compounds are useful for treating cancer and related proliferative diseases. Pharmaceutical compositions containing compounds of Formula I and methods of treatment comprising administering compounds of Formula I are also disclosed.

  式 I 的化合物及其药学上可接受的盐公开了式 I。本文公开了变量 X1、X2 和 R1-4。这些化合物可用于治疗癌症和相关的增殖性疾病。还公开了含有式 I 化合物的药物组合物和包括施用式 I 化合物的治疗方法。
• FUROQUINOLINEDIONES AS INHIBITORS OF TDP2
  申请人：The United States of America, as represented by The Secretary, Department of Health and Human Services

  公开号：EP3242881B1

  公开（公告）日：2020-04-29
• [EN] FUROQUINOLINEDIONES AS INHIBITORS OF TDP2<br/>[FR] FUROQUINOLINEDIONES SERVANT D'INHIBITEURS DE TDP2
  申请人：USA

  公开号：WO2016112304A1

  公开（公告）日：2016-07-14

  Compounds of Formula I and the pharmaceutically acceptable salts thereof are disclosed Formula I. The variables X1, X2, and R1-4 are disclosed herein. The compounds are useful for treating cancer and related proliferative diseases. Pharmaceutical compositions containing compounds of Formula I and methods of treatment comprising administering compounds of Formula I are also disclosed.
• 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.