6-Chloroquinoline-2-thiol | 1330752-16-3

• 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
• 英文名称: 6-Chloroquinoline-2-thiol
• 英文别名: 6-chloro-1H-quinoline-2-thione
• CAS: 1330752-16-3
• 化学式: C₉H₆ClNS
• 分子量: 195.672
• InChiKey: HXWQADMOCGNSCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-Chloroquinoline-2-thiol 在 potassium ferricyanide 作用下， 以 乙醇 、 水 为溶剂， 生成 bis(6-chloroquinolin-2-yl) disulfide
  参考文献：
  名称：

  From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric Chloroquinolinesulfonyl Chlorides

  摘要：

  The action of sodium methanethiolate (in boiling DMF) on x,y-dichloroquinolines (1) (x=3 or 6, y=2 or 4) occured via chlorine ipso-substitution followed by methanethiolato-S-demthylation to yield x,y-quinolinedithiolates 2A which were: i) subjected to S-methylation, ii) oxidatively chlorinated to y,y'-bis(x-chloro-x-quinolinesulfonyl chlorides (5). Oxidative chlorination of y,y'-bis(x-chloro quinolinyl) disulfides (7) led to x-chloro-y-quinolinesulfonyl chlorides (8) accompanied by x,y-dichloroquinolines (1). Both quinolinessulfonyl chlorides 5 and 8 were efficiently converted to the corresponding quinolinesulfonamides 6 and 9.

  DOI：

  10.3987/com-09-11855
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 6-Chloroquinoline-2-thiol
  参考文献：
  名称：

  From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric Chloroquinolinesulfonyl Chlorides

  摘要：

  The action of sodium methanethiolate (in boiling DMF) on x,y-dichloroquinolines (1) (x=3 or 6, y=2 or 4) occured via chlorine ipso-substitution followed by methanethiolato-S-demthylation to yield x,y-quinolinedithiolates 2A which were: i) subjected to S-methylation, ii) oxidatively chlorinated to y,y'-bis(x-chloro-x-quinolinesulfonyl chlorides (5). Oxidative chlorination of y,y'-bis(x-chloro quinolinyl) disulfides (7) led to x-chloro-y-quinolinesulfonyl chlorides (8) accompanied by x,y-dichloroquinolines (1). Both quinolinessulfonyl chlorides 5 and 8 were efficiently converted to the corresponding quinolinesulfonamides 6 and 9.

  DOI：

  10.3987/com-09-11855

文献信息

• Design, synthesis, biological evaluation and in silico studies of novel quinoline derivatives as potential radioprotective molecules targeting the TLR2 and p53 pathways
  作者：Yaowen Cui、Zhaolun He、Tingting Chen、Xinjian Ren、Jing Xu、shouguo Zhang、Tao Peng、Shuchen Liu、Lin Wang

  DOI：10.1016/j.ejmech.2024.116239

  日期：2024.3

  major threats to human health and public security. In this paper, in order to find the potential novel compounds decreasing the radiation-induced damage by targeting p53 apoptosis pathway and TLR2 passway, a series of novel quinoline derivatives were designed, synthesized, and evaluated their biological activities. Most of the synthesized compounds showed significant radioprotective effects and the

  太空电离辐射、辐射装置或核灾难是对人类健康和公共安全的重大威胁。本文以p53凋亡途径和TLR2通路为靶点，寻找潜在的减轻辐射损伤的新型化合物，设计、合成了一系列新型喹啉衍生物，并评价了它们的生物活性。合成的大多数化合物均表现出显着的辐射防护作用，其中该化合物的性能最好。因此，我们验证了其辐射防护活性并研究了其优异活性的机制。结果表明，该化合物不仅显着提高了小鼠受辐射致死后30天的存活率（80%），而且显着减轻了辐射对小鼠造血系统和肠道组织的损伤。机理研究表明，该化合物作用于p53通路，减少辐射诱导的细胞凋亡，同时刺激TLR2上调辐射防护因子的表达。分子动力学研究表明该化合物能够有效地与TLR2蛋白结合，并进一步揭示了结合机制。总而言之，我们研究的所有结果表明喹啉衍生物是一种有效的辐射防护化合物，具有进一步开发的巨大治疗潜力。
• Ts₂O Promoted Deoxygenative C–H Dithiocarbonation of Quinoline <i>N</i>-Oxides with Potassium <i>O</i>-Alkyl Xanthates
  作者：Meng-Yang Zhao、Jia-Jun Tang、Ying-Jun Lin、Zhong-Ying Tian、Sha Peng、Long-Yong Xie

  DOI：10.1021/acs.joc.4c00031

  日期：2024.4.19

  C–H dithiocarbonation of quinoline N-oxides with various potassium O-alkyl xanthates. The reaction performed well under transition-metal-free, base-free, and room-temperature conditions with wide substrate tolerance. Employing potassium O-tert-butyl xanthate (tBuOCS2K) as a nucleophile, some valuable quinoline-2-thiones were unexpectedly obtained in a one-pot reaction without any additional base.

  通过 Ts 2 O 促进的喹啉 N-氧化物与各种 O-烷基黄原酸钾的脱氧 C-H 二硫代碳酸化反应，开发了一种简单、有效且实用的合成 S-喹啉黄原酸的方法。该反应在无过渡金属、无碱和室温条件下表现良好，具有广泛的底物耐受性。使用O-叔丁基黄原酸钾( t BuOCS 2 K)作为亲核试剂，在没有任何额外碱的情况下，在一锅反应中意外地获得了一些有价值的喹啉-2-硫酮。
• US4216284A
  申请人：——

  公开号：US4216284A

  公开（公告）日：1980-08-05
• From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric Chloroquinolinesulfonyl Chlorides
  作者：Krzysztof Marciniec、Andrzej Maślankiewicz

  DOI：10.3987/com-09-11855

  日期：——

  The action of sodium methanethiolate (in boiling DMF) on x,y-dichloroquinolines (1) (x=3 or 6, y=2 or 4) occured via chlorine ipso-substitution followed by methanethiolato-S-demthylation to yield x,y-quinolinedithiolates 2A which were: i) subjected to S-methylation, ii) oxidatively chlorinated to y,y'-bis(x-chloro-x-quinolinesulfonyl chlorides (5). Oxidative chlorination of y,y'-bis(x-chloro quinolinyl) disulfides (7) led to x-chloro-y-quinolinesulfonyl chlorides (8) accompanied by x,y-dichloroquinolines (1). Both quinolinessulfonyl chlorides 5 and 8 were efficiently converted to the corresponding quinolinesulfonamides 6 and 9.