7-chloro-4-(phenylthio)quinoline | 1025-43-0

• 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-(phenylthio)quinoline
• 英文别名: 7-Chloro-4-(phenylsulfanyl)quinoline；7-chloro-4-phenylsulfanylquinoline
• CAS: 1025-43-0
• 化学式: C₁₅H₁₀ClNS
• 分子量: 271.77
• InChiKey: WOBNXFDIMVTLPY-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  437.4±25.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-(phenylthio)quinoline 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以60%的产率得到7-chloro-4-(phenylsulfonyl)quinoline
  参考文献：
  名称：

  7-Chloro-4-phenylsulfonyl quinoline, a new antinociceptive and anti-inflammatory molecule: Structural improvement of a quinoline derivate with pharmacological activity

  摘要：

  The present study was designed to examine the antinociceptive and anti-inflammatory effects of 7-chloro-4-phenylsulfonyl quinoline (PSOQ). Mice were orally (p.o) pretreated with PSOQ (0.01-10 mg/kg), meloxicam (10 mg/kg), 30 min prior to the acetic acid, hot-plate and open field tests. PSOQ reduced abdominal writhing induced by acetic acid, while meloxicam presented no effect. The latency time in the hot-plate test and locomotor/exploratory activities in the open field test were not altered by treatments. In order to evaluate the gastric tolerability after oral administration of PSOQ or meloxicam (10 mg/kg), mice were fasted for 18 h prior to drug exposure. Four hours later, the development of lesions was assessed. PSOQ and meloxicam did not induce ulcer at the dose and time evaluated. Indeed, anti-inflammatory and anti-edematogenic properties of PSOQ were investigated. For this, animals were pretreated with PSOQ (0.01-50 mg/kg; p.o.), meloxicam (50 mg/kg; p.o.), 30 min prior to croton oil application. PSOQ and meloxicam (50 mg/kg) diminished the edema formation and myeloperoxidase activity induced by croton oil in the ear tissue. Taken together these data demonstrated that PSOQ exerts acute anti-inflammatory and antinociceptive actions, suggesting that it may represent an alternative in the development of future new therapeutic strategies. (C) 2017 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.yrtph.2017.08.014
• 作为产物：
  描述：

  4,7-二氯喹啉 、 苯硫酚 在 air 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以96%的产率得到7-chloro-4-(phenylthio)quinoline
  参考文献：
  名称：

  Direct synthesis of 4-organylsulfenyl-7-chloro quinolines and their toxicological and pharmacological activities in Caenorhabditis elegans

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.01.037

文献信息

• Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents
  作者：Valter E. Murie、Paula V. Nicolino、Thiago dos Santos、Guido Gambacorta、Rodolfo H. V. Nishimura、Icaro S. Perovani、Luciana C. Furtado、Leticia V. Costa-Lotufo、Anderson Moraes de Oliveira、Ricardo Vessecchi、Ian R. Baxendale、Giuliano C. Clososki

  DOI：10.1021/acs.joc.1c01521

  日期：2021.10.1

  We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium intermediates, which were reacted with different electrophiles. Mixed lithium-zinc reagents allowed the synthesis of halogenated and arylated derivatives. Some

  我们已经在温和条件下通过 7-氯喹啉的氧化制备了功能化喹啉库，采用间歇和连续流动条件。制备涉及混合锂镁中间体的产生，这些中间体与不同的亲电试剂反应。混合锂锌试剂允许合成卤化和芳基化衍生物。一些合成的 4-甲醇喹啉显示出有趣的抗增殖特性，它们的羟基是合适的氨基生物电子等排体。我们还报告了光学活性衍生物的两步法。