1-(4-甲烷磺酰基-苯基)-2-苯基-1,2-乙二酮 | 54945-18-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(4-甲烷磺酰基-苯基)-2-苯基-1,2-乙二酮
• 英文名称: 1-(4-methanesulfonyl-phenyl)-2-phenyl-ethane-1,2-dione
• 英文别名: 1-(4-(methylsulfonyl)phenyl)-2-phenylethane-1,2-dione；1-(4-methylsulfonylphenyl)-2-phenyl-1,2-ethanedione；4-methanesulfonyl-benzil；4-Methansulfonyl-benzil；1-(4-methylsulfonylphenyl)-2-phenylethane-1,2-dione
• CAS: 54945-18-5
• 化学式: C₁₅H₁₂O₄S
• 分子量: 288.324
• InChiKey: RJECBBUZNVRUHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  1-(4-甲烷磺酰基-苯基)-2-苯基-1,2-乙二酮 在 palladium on activated charcoal 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.0h， 生成 2-(4-Methanesulfonyl-phenyl)-3-phenyl-pyrazine
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors

  摘要：

  Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO2NH2)/methylsulfonyl (SO2Me)-phenyl pharmaco-phores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure-activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.033
• 作为产物：
  描述：

  1-(4-(methylthio)phenyl)-2-phenylethane-1,2-dione 在 双氧水 、 溶剂黄146 作用下， 反应 5.0h， 生成 1-(4-甲烷磺酰基-苯基)-2-苯基-1,2-乙二酮
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors

  摘要：

  Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO2NH2)/methylsulfonyl (SO2Me)-phenyl pharmaco-phores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure-activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.033

文献信息

• Design and synthesis of new 2,4,5-triarylimidazole derivatives as selective cyclooxygenase (COX-2) inhibitors
  作者：A. Zarghi、S. Arfaei、R. Ghodsi

  DOI：10.1007/s00044-011-9710-5

  日期：2012.8

  imidazole (11f) was identified as a selective COX-2 inhibitor (COX-2 IC50 = 0.15 μM; selectivity index = 75) that was less potent than the reference drug celecoxib (COX-2 IC50 = 0.06 μM; SI = 405). A molecular modeling study where 11f was docked in the binding site of COX-2 showed that the methylsulfonyl pharmacophore group is oriented in the vicinity of the COX-2 secondary pocket (Arg513, Phe518, Gly519

  合成了一组新的具有甲基磺酰基药效基团的2,4,5-三芳基咪唑衍生物，并评估了其生物活性对环氧合酶-2（COX-2）的抑制活性。通过改变C-2苯环对位的取代基来确定体外COX-1 / COX-2的构效关系。在2,4,5-三芳基咪唑中，2-（4-羟基苯基）-4-（4-甲基磺酰基苯基）-5-苯基-1 H咪唑（11f）被鉴定为选择性COX-2抑制剂（COX-2 IC50 = 0.15μM；选择性指数= 75），其效力低于参考药物塞来昔布（COX-2 IC50 = 0.06μM； SI = 405）。分子建模研究，其中11f端接于COX-2的结合位点的Aβ显示甲基磺酰基药效团基团定向在COX-2二级口袋（Arg 513，Phe 518，Gly 519和Val 523）附近。获得的结构活性数据表明，COX-1 / COX-2抑制作用对C-2苯基取代基的性质敏感。
• Antiinflammatory 4,5-diarylimidazoles as selective cyclooxygenase inhibitors
  作者：Thomas E. Barta、Michael A. Stealey、Paul W. Collins、Richard M. Weier

  DOI：10.1016/s0960-894x(98)00627-1

  日期：1998.12

  The synthesis and activity of a series of 4,5-diarylimidazole analogs are described. One analog had an IC50 of 80 nM, was 6750-selective against COX-1, and demonstrated in vivo potency in the mouse air pouch model.

  描述了一系列4,5-二芳基咪唑类似物的合成和活性。一种类似物的IC50为80 nM，对COX-1具有6750选择性，并在小鼠气袋模型中显示出体内效力。
• Investigating the Structure–Activity Relationship of 1,2,4-Triazine G-Protein-Coupled Receptor 84 (GPR84) Antagonists
  作者：Amit Mahindra、Laura Jenkins、Sara Marsango、Mark Huggett、Margaret Huggett、Lindsay Robinson、Jonathan Gillespie、Muralikrishnan Rajamanickam、Angus Morrison、Stuart McElroy、Irina G. Tikhonova、Graeme Milligan、Andrew G. Jamieson

  DOI：10.1021/acs.jmedchem.2c00804

  日期：2022.8.25

  reported the discovery of a novel triazine GPR84 competitive antagonist 1. Here, we describe an extensive structure–activity relationship (SAR) of antagonist 1 and also present in silico docking with supporting mutagenesis studies that reveals a potential binding pose for this type of orthosteric antagonist. Lead compound 42 is a potent GPR84 antagonist with a favorable pharmacokinetic (PK) profile suitable

  G 蛋白偶联受体 84 (GPR84) 是一种促炎性孤儿 G 蛋白偶联受体，与几种炎症和纤维化疾病有关。已经开发了几种靶向 GPR84 的激动剂和拮抗剂配体。然而，一种进入 II 期临床试验的非竞争性受体阻滞剂未能证明疗效。需要新的高质量拮抗剂来研究 GPR84 的病理生理作用并验证 GPR84 作为治疗靶点。我们之前报道了一种新型三嗪 GPR84 竞争性拮抗剂1的发现。在这里，我们描述了拮抗剂1的广泛构效关系 (SAR)并且还存在于与支持诱变研究的计算机对接中，该研究揭示了这种类型的正构拮抗剂的潜在结合姿势。先导化合物42是一种有效的 GPR84 拮抗剂，具有良好的药代动力学 (PK) 特征，适合进一步的药物开发。
• The Absorption Spectra of Tetracyclones. IV^1,2
  作者：Stephen B. Coan、Donald E. Trucker、Ernest I. Beckerr

  DOI：10.1021/ja01606a018

  日期：1955.1
• Practical Method for Transforming Alkynes into α-Diketones
  作者：Zhonghui Wan、Chauncey D. Jones、David Mitchell、John Y. Pu、Tony Y. Zhang

  DOI：10.1021/jo051793g

  日期：2006.1.1

  [GRAPHICS]Oxidation of alkynes to alpha-dicarbonyl derivatives through a convenient one-pot procedure via a Bronsted acid-promoted "hydration" and a DMSO-based oxidation sequence has been achieved in high yields. The scope and limitations of the reaction have also been investigated.