1-[4-(Methanesulfonyl)phenyl]-3-(4-methylphenyl)prop-2-en-1-one | 819792-64-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-[4-(Methanesulfonyl)phenyl]-3-(4-methylphenyl)prop-2-en-1-one
• 英文别名: 3-(4-methylphenyl)-1-(4-methylsulfonylphenyl)prop-2-en-1-one
• CAS: 819792-64-8
• 化学式: C₁₇H₁₆O₃S
• 分子量: 300.378
• InChiKey: AITOCJUKULFGJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-[4-(Methanesulfonyl)phenyl]-3-(4-methylphenyl)prop-2-en-1-one 、 溶剂黄146 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以53%的产率得到1-(3-(4-(methylsulfonyl)phenyl)-5-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis and biological evaluation of N-substituted-3,5-diphenyl-2-pyrazoline derivatives as cyclooxygenase (COX-2) inhibitors

  摘要：

  Eighteen new 1-N-substituted-3,5-diphenyl-2-pyrazoline derivatives have been synthesized and cyclooxygenase (COX-1 and COX-2) inhibitory activities have been evaluated. The results of these biological assays showed that all of new derivatives are not endowed with improved anti-inflammatory activity against COX-1, but some of them showed a good activity against COX-2. To evaluate the binding mode of the most significative compounds (2d, 2f, 2g and 2k) docking studies were carried out. These studies confirmed biological data, in fact these compounds were able to fit into the active site of COX-2. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.005
• 作为产物：
  描述：

  4-甲砜基苯乙酮 、 对甲基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-[4-(Methanesulfonyl)phenyl]-3-(4-methylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  作为选择性环氧合酶 2 抑制剂的新型苯并[4,5]咪唑并[1,2-a]嘧啶衍生物：设计、合成、对接研究和生物学评价

  摘要：

  本研究旨在合成和评价一系列具有甲基磺酰基的苯并[4,5]咪唑并[1,2- a ]嘧啶作为COX-2（环氧合酶-2）抑制剂药效团。使用 Autodock 程序进行了分子建模研究，结果表明甲基磺酰基药效团已充分置于 COX-2 活性位点。还评估了体外和体内 COX-2 抑制作用。在体外试验中，所有新合成的化合物对 COX-2 酶的抑制作用表现出中等到良好的选择性。然而，化合物 2-(4-(methylsulfonyl) phenyl)-4-phenylbenzo[4,5]imidazo[1,2- a ]pyrimidine ( 5a ) 显示出最高的 COX-2 抑制作用 (IC 50: 0.05 μM) 甚至超过作为参考药物的塞来昔布 (IC 50 : 0.06 μM)。对于体内研究，使用了书写反射测试，结果表明所有合成的化合物都具有良好的剂量依赖性抗伤害感受活性。体内评价还表明化合物2-(

  DOI：

  10.1007/s00044-023-03022-0

文献信息

• Design, Synthesis and Biological Evaluation of New 1,3-diphenyl-3- (phenylamino)propan-1-ones as Selective Cyclooxygenase (COX-2) Inhibitors
  作者：Shabnam Farzaneh、Soraya Shahhosseini、Hadi Arefi、Bahram Daraei、Marjan Esfahanizadeh、Afshin Zarghi

  DOI：10.2174/1573406414666180525133221

  日期：2018.10.3

  Docking study was performed using AutoDock vina software. In vitro COX-1 and COX- 2 isozyme inhibition studies were accomplished to obtain structure activity relationship data. The in vitro antiplatelet aggregation activity was determined by turbidimetric procedure. Results: In vitro COX inhibition assay showed that except compound 8c, all derivatives were selective COX-2 inhibitors with IC50 values in the

  背景：前列腺素是花生四烯酸通过环氧合酶（COX）途径生物合成的类花生酸家族。很好地建立了两种COX异构体：COX-1，COX-2。有证据支持环氧合酶2在某些病理状况（例如炎症和癌症）中起关键作用的观点。 目的：设计合成一组新的1,3-二苯基-3-（苯氨基）丙烷-1-酮，研究其对COX-2的抑制活性和对血小板聚集的抑制作用。 方法：使用AutoDock vina软件进行对接研究。进行体外COX-1和COX-2同工酶抑制研究以获得结构活性关系数据。通过比浊法确定体外抗血小板聚集活性。 结果：体外COX抑制试验表明，除化合物8c外，所有衍生物均为选择性COX-2抑制剂，IC50值在0.20-0.35 µM的有效范围内，并具有较高的COX-2选择性指数（SI）。分子建模和对接研究表明，合成的化合物具有与已知抑制剂SC-558相似的结合力，并且SO2Me基团插入了COX-2二级口袋（Val523，P
• Synthesis and biological evaluation of N-substituted-3,5-diphenyl-2-pyrazoline derivatives as cyclooxygenase (COX-2) inhibitors
  作者：Rossella Fioravanti、Adriana Bolasco、Fedele Manna、Francesca Rossi、Francisco Orallo、Francesco Ortuso、Stefano Alcaro、Roberto Cirilli

  DOI：10.1016/j.ejmech.2010.10.005

  日期：2010.12

  Eighteen new 1-N-substituted-3,5-diphenyl-2-pyrazoline derivatives have been synthesized and cyclooxygenase (COX-1 and COX-2) inhibitory activities have been evaluated. The results of these biological assays showed that all of new derivatives are not endowed with improved anti-inflammatory activity against COX-1, but some of them showed a good activity against COX-2. To evaluate the binding mode of the most significative compounds (2d, 2f, 2g and 2k) docking studies were carried out. These studies confirmed biological data, in fact these compounds were able to fit into the active site of COX-2. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Novel Benzo[4,5]imidazo[1,2-a]pyrimidine derivatives as selective Cyclooxygenase-2 Inhibitors: Design, synthesis, docking studies, and biological evaluation
  作者：Maryam Bayanati、Mona Khoramjouy、Mehrdad Faizi、Mahsa Azami Movahed、Mohammad Mahboubi-Rabbani、Afshin Zarghi

  DOI：10.1007/s00044-023-03022-0

  日期：2023.3

  of benzo[4,5]imidazo[1,2-a]pyrimidine having a methylsulfonyl group as COX-2 (cyclooxygenase-2) inhibitor pharmacophore. Molecular modeling studies were performed using the Autodock program, and the results demonstrated that methylsulfonyl pharmacophore was adequately placed into the COX-2 active site. The in vitro and in vivo COX-2 inhibitory effects were also evaluated. In the in vitro assay, all newly

  本研究旨在合成和评价一系列具有甲基磺酰基的苯并[4,5]咪唑并[1,2- a ]嘧啶作为COX-2（环氧合酶-2）抑制剂药效团。使用 Autodock 程序进行了分子建模研究，结果表明甲基磺酰基药效团已充分置于 COX-2 活性位点。还评估了体外和体内 COX-2 抑制作用。在体外试验中，所有新合成的化合物对 COX-2 酶的抑制作用表现出中等到良好的选择性。然而，化合物 2-(4-(methylsulfonyl) phenyl)-4-phenylbenzo[4,5]imidazo[1,2- a ]pyrimidine ( 5a ) 显示出最高的 COX-2 抑制作用 (IC 50: 0.05 μM) 甚至超过作为参考药物的塞来昔布 (IC 50 : 0.06 μM)。对于体内研究，使用了书写反射测试，结果表明所有合成的化合物都具有良好的剂量依赖性抗伤害感受活性。体内评价还表明化合物2-(