2-(3,4-dichlorophenyl)-1-(4-methylsulfanylphenyl)ethanone | 708276-17-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(3,4-dichlorophenyl)-1-(4-methylsulfanylphenyl)ethanone
• CAS: 708276-17-9
• 化学式: C₁₅H₁₂Cl₂OS
• mdl: MFCD22853870
• 分子量: 311.232
• InChiKey: RDRUXURUCQZYKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  454.2±40.0 °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：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3,4-dichlorophenyl)-1-(4-methylsulfanylphenyl)ethanone 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以53%的产率得到2-(3,4-dichlorophenyl)-1-(4-methanesulfonylphenyl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors

  摘要：

  A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical. and clinical evaluation.

  DOI：

  10.1021/jm049882t
• 作为产物：
  描述：

  茴香硫醚 、 2',3',4'-三氯苯乙酮 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以72%的产率得到2-(3,4-dichlorophenyl)-1-(4-methylsulfanylphenyl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors

  摘要：

  A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical. and clinical evaluation.

  DOI：

  10.1021/jm049882t

文献信息

• β-Amino acid derivatives as mitochondrial complex III inhibitors of L. donovani: A promising chemotype targeting visceral leishmaniasis
  作者：Pragya Chandrakar、Naresh Gunaganti、Naveen Parmar、Ashok Kumar、Sandeep Kumar Singh、Mamunur Rashid、M. Wahajuddin、Kalyan Mitra、Tadigopula Narender、Susanta Kar

  DOI：10.1016/j.ejmech.2019.111632

  日期：2019.11

  were synthesized and evaluated for their antileishmanial efficacy against experimental visceral leishmaniasis (VL). Among all synthesized derivatives, 10c showed promising antileishmanial efficacy against both extracellular promastigote and intracellular amastigote (IC50 8.2 μM and 20.5 μM respectively) of L. donovani with negligible cytotoxic effect towards J774 macrophages and Vero cells. 10c effectively

  β-氨基酸及其类似物不仅因为它们的抗菌和抗真菌活性，而且由于其在设计具有更高口服生物利用度和对代谢降解的抵抗力的拟肽药物中的用途而受到越来越多的关注。在这项研究中，合成了一系列的α-苯基取代的查耳酮，α-苯基，β-氨基取代的二氢查耳酮和β-氨基酸衍生物，并评估了它们对实验性内脏利什曼病的抗兽药功效。在所有合成的衍生物中，10c表现出对诺瓦氏乳杆菌的细胞外前鞭毛体和细胞内鞭毛体（分别为IC50 8.2μM和20.5μM）的有希望的抗疟疾功效，对J774巨噬细胞和Vero细胞的细胞毒性作用可忽略。10c有效减轻脾脏和肝脏的寄生虫负担（> 90％）在VL的仓鼠和Balb / c模型中均无肝毒性。体外药代动力学分析表明，Balb / c小鼠的胃液和血浆中的10c稳定在10μg/ ml。对分子机理的进一步分析表明，10c通过使质膜去极化而不是形成非特异性孔而进入寄生虫，并诱导分子事件（例如线粒体膜电
• Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors
  作者：Francisco Caturla、Juan-Miguel Jiménez、Núria Godessart、Mercè Amat、Alvaro Cárdenas、Lídia Soca、Jordi Beleta、Hamish Ryder、María I. Crespo

  DOI：10.1021/jm049882t

  日期：2004.7.1

  A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical. and clinical evaluation.