2-(4-bromophenyl)-1-(4-methanesulfonylphenyl)ethanone | 404966-43-4

• 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-(4-bromophenyl)-1-(4-methanesulfonylphenyl)ethanone
• 英文别名: 2-(4-Bromophenyl)-1-(4-methylsulfonylphenyl)ethanone
• CAS: 404966-43-4
• 化学式: C₁₅H₁₃BrO₃S
• 分子量: 353.236
• InChiKey: DIKOVJRRFJCVHU-UHFFFAOYSA-N

物化性质

• 熔点：
  188-191 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  533.8±50.0 °C(Predicted)
• 密度：
  1.474±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  盐酸氨基脲 、 2-(4-bromophenyl)-1-(4-methanesulfonylphenyl)ethanone 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 C₁₆H₁₆BrN₃O₃S
  参考文献：
  名称：

  Syntheses of 4,5-Diaryl-1,2,3-thiadiazoles

  摘要：

  Reaction of thionyl chloride with semicarbazones of 1-(4-methylsulfonylphenyl)-2-(4-substituted pheny)lethanone gave 1-(4-methylsulfonylphenyl)-5-(4-substituted) pheny-1,2,3-thiadiazoles 5. Compounds 5-phenyl-4-(substitutedphenyl)-1,2,3-thiadiazoles 14 were similarly prepared. Chlorosulfonation of the latter followed by ammonia gave the desired compounds 5-(4-aminosulfonylphenyl)-4-(substituted) phenyl-1,2,3-thiadiazoles 6.

  DOI：

  10.1080/104265090884283
• 作为产物：
  描述：

  茴香硫醚 在 三氯化铝 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-(4-bromophenyl)-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

文献信息

• 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.
• Syntheses of 4,5-Diaryl-1,2,3-thiadiazoles
  作者：Lila Karimi、Latifeh Navidpour、Mohsen Amini、Abbas Shafiee

  DOI：10.1080/104265090884283

  日期：2005.7.1

  Reaction of thionyl chloride with semicarbazones of 1-(4-methylsulfonylphenyl)-2-(4-substituted pheny)lethanone gave 1-(4-methylsulfonylphenyl)-5-(4-substituted) pheny-1,2,3-thiadiazoles 5. Compounds 5-phenyl-4-(substitutedphenyl)-1,2,3-thiadiazoles 14 were similarly prepared. Chlorosulfonation of the latter followed by ammonia gave the desired compounds 5-(4-aminosulfonylphenyl)-4-(substituted) phenyl-1,2,3-thiadiazoles 6.