7-chloro-4-(p-tolylthio)quinoline | 161467-72-7

• 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-4-(p-tolylthio)quinoline
• 英文别名: 7-chloro-4-p-tolylmercapto-quinoline；7-Chlor-4-p-tolylmercapto-chinolin；7-Chloro-4-(4-methylphenyl)sulfanylquinoline
• CAS: 161467-72-7
• 化学式: C₁₆H₁₂ClNS
• 分子量: 285.797
• InChiKey: ZZAHGYPBJFJSKR-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C
• 沸点：
  452.7±30.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-4-(p-tolylthio)quinoline 在 potassium permanganate 、 溶剂黄146 作用下， 反应 5.0h， 以70%的产率得到7-chloro-4-tosylquinoline
  参考文献：
  名称：

  Tripathi, R. C.; Saxena, M.; Chandra, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 2, p. 164 - 166

  摘要：

  DOI：
• 作为产物：
  描述：

  4,7-二氯喹啉 、 4-甲苯硫酚 在 苯 作用下， 生成 7-chloro-4-(p-tolylthio)quinoline
  参考文献：
  名称：

  Illuminati; Santucci, Gazzetta Chimica Italiana, 1953, vol. 83, p. 1106,1118

  摘要：

  DOI：

文献信息

• 4-Hydroxyquinolines. Effect of a 7-Substituent on the Displaceability of the Hydroxyl Group¹
  作者：Gabriello Illuminati、Ludovico Santucci

  DOI：10.1021/ja01629a082

  日期：1955.12
• Illuminati; Santucci, Gazzetta Chimica Italiana, 1953, vol. 83, p. 1106,1118
  作者：Illuminati、Santucci

  DOI：——

  日期：——
• Tripathi, R. C.; Saxena, M.; Chandra, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 2, p. 164 - 166
  作者：Tripathi, R. C.、Saxena, M.、Chandra, S.、Saxena, Anil K.

  DOI：——

  日期：——
• Direct synthesis of 4-organylsulfenyl-7-chloro quinolines and their toxicological and pharmacological activities in Caenorhabditis elegans
  作者：Willian G. Salgueiro、Maurício C.D.F. Xavier、Luis Fernando B. Duarte、Daniela F. Câmara、Daiandra A. Fagundez、Ana Thalita G. Soares、Gelson Perin、Diego Alves、Daiana Silva Avila

  DOI：10.1016/j.ejmech.2014.01.037

  日期：2014.3

  We describe herein our results on the synthesis and biological properties in Caenorhabditis elegans of a range of 4-organylsulfenyl-7-chloroquinolines. This class of compounds have been easily synthesized in high yields by direct reaction of 4,7-dichloroquinoline with organylthiols using DMSO as solvent at room temperature under air atmosphere and tolerates a range of substituents in the organylsulfenyl moiety. We have performed a toxicological and pharmacological screening of the synthesized 4-organylsulfenyl-7-chloroquinolines in vivo in C elegans acutely exposed to these compounds, under per se and stress conditions. Hence, we determined the lethal dose 50% (LD50), in order to choose a nonlethal concentration (10 mu M) and verified that at that concentration some of the compounds depicted protective action against the induced damage inflicted by paraquat, a superoxide generator. Two compounds (3c and 3h) reduced the toxicity inflicted by paraquat above survival, reproduction and longevity of the worms, at least in part, by reducing the reactive oxygen species (ROS) generated by the toxicant exposure. Besides, these compounds increased the quantities of superoxide dismutase (SOD-3::GFP) and catalase (CTL-1,2,3::GFP), antioxidant enzymes. We concluded that the protective effects of the compounds observed in this study might have been a hormetic response dependent of the transcriptional factor DAF-16/FOXO, causing a non-lethal oxidative stress that protects against the subsequently damage induced by paraquat. (C) 2014 Elsevier Masson SAS. All rights reserved.