乙酮,2-溴-1-[4-(甲硫基)苯基]-2-苯基- | 103089-98-1

• 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: 乙酮,2-溴-1-[4-(甲硫基)苯基]-2-苯基-
• 英文名称: 2-bromo-1-(4''-(methylsulfanyl)phenyl)-2-phenyl-1-ethanone
• 英文别名: 2-bromo-2-phenyl-1-(4-methylthiophenyl)ethanone；Ethanone, 2-bromo-1-[4-(methylthio)phenyl]-2-phenyl-；2-bromo-1-(4-methylsulfanylphenyl)-2-phenylethanone
• CAS: 103089-98-1
• 化学式: C₁₅H₁₃BrOS
• 分子量: 321.238
• InChiKey: VEWKGZMQJDVPJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 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：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酮,2-溴-1-[4-(甲硫基)苯基]-2-苯基- 在 formamide 作用下， 以 水 为溶剂， 以65%的产率得到4-phenyl-5-(4-methylthiophenyl)-1H-imidazole
  参考文献：
  名称：

  Antihypertensive 4,5-diaryl-1H-imidazole-2-methanol derivatives

  摘要：

  抗高血压药物4-苯基-5-(4-甲磺基苯基)-α，α-双(三氟甲基)-1 H-咪唑-2-甲醇衍生物在高血压治疗中具有用处。

  公开号：

  US04576958A1
• 作为产物：
  描述：

  茴香硫醚 在 三氯化铝 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 乙酮,2-溴-1-[4-(甲硫基)苯基]-2-苯基-
  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

• [EN] PHARMACEUTICAL COMPOUNDS THAT REGENERATE IN VIVO TECHNICAL FIELD OF THE INVENTION<br/>[FR] COMPOSES PHARMACEUTIQUES QUI SE REGENERENT IN VIVO
  申请人：SYNCHRONY BIOSCIENCES INC

  公开号：WO2005054204A3

  公开（公告）日：2005-09-15
• Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors
  作者：Sunil K. Singh、V. Saibaba、V. Ravikumar、Santosh V. Rudrawar、Pankaj Daga、C.Seshagiri Rao、V. Akhila、P. Hegde、Y.Koteswar Rao

  DOI：10.1016/j.bmc.2004.01.033

  日期：2004.4

  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.
• Synthesis, spectral studies and biological evaluation of a novel series of 2-substituted-5,6-diarylsubstituted imidazo(2,1-b)-1,3,4-thiadiazole derivatives as possible anti-tubercular agents
  作者：Mahesh B. Palkar、Malleshappa N. Noolvi、Veeresh S. Maddi、Mangala Ghatole、Laxmivenkat G. Nargund

  DOI：10.1007/s00044-011-9646-9

  日期：2012.7

  A novel series of 18 analogs of 2-substituted-5,6-diarylsubstituted imidazo(2,1-b)-1,3,4-thiadiazole 6a-r have been synthesized by the reaction of 2-amino-5-substituted-1,3,4-thiadiazoles 5a-d and an appropriately substituted alpha-bromo-1,2-(p-substituted)diaryl-1-ethanones 4a-e. Structures of these compounds were established by physiochemical, elemental analysis and spectral data. All the title compounds were tested for their in-vitro anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv using Alamar Blue susceptibility test and the activity expressed as the minimum inhibitory concentration (MIC) in mu g/ml. Among synthesized compounds, compound 6h (MIC = 1.25 mu g/ml) exhibited excellent anti-tubercular activity with respect to other synthesized compounds and reference drugs. Compounds 6c, 6f, and 6g have also displayed an encouraging anti-tubercular activity profile. Further, some title compounds were also assessed for their cytotoxic activity (IC50) against in a mammalian Vero cell line using MTT assay. The results reveal that these compounds exhibit anti-tubercular activity at non-cytotoxic concentrations.
• Synthesis and biological evaluation of 2-trifluoromethyl/sulfonamido-5,6-diaryl substituted imidazo[2,1-b]-1,3,4-thiadiazoles: A novel class of cyclooxygenase-2 inhibitors
  作者：Andanappa K. Gadad、Mahesh B. Palkar、K. Anand、Malleshappa N. Noolvi、Thippeswamy S. Boreddy、J. Wagwade

  DOI：10.1016/j.bmc.2007.09.038

  日期：2008.1

  A series of 2-trifluoromethyl/sulfonamido-5,6-diaryl substituted imidazo[2,1-b]-1,3,4-thiadiazole derivatives 15a-j have been synthesized by the reaction of 2-amino-5-trifluoromethyl/sulfonamido-1,3,4-thiadiazoles 14a-b and appropriately substituted alpha-bromo-1,2-(p-substituted)diaryl-l-ethanones 13a-h. Structures of these compounds were established by IR, H-1 NMR, C-13 NMR, Mass, and HRMS data. The selected compounds were evaluated for their preliminary in vitro cyclooxygenase inhibitory activity against COX-2 and COX-lenzymes using colorimetric method. The compounds tested showed selective inhibitory activity toward COX-2 (80.6-49.4%) over COX-1 (30.6-8.6), amongst them compounds 15f and 15j showed appreciable COX-2 selective inhibitory activity. These compounds also exhibited significant anti-inflammatory activity (70.09-42.32%), which is comparable to that of celecoxib in the carrageenan-induced rat paw edema method. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, cyclooxygenase inhibitory effects, and molecular modeling study of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and -2-alkylsulfonyl-1 H -imidazole derivatives
  作者：Amir Assadieskandar、Amirali Amirhamzeh、Marjan Salehi、Keriman Ozadali、Seyed Nasser Ostad、Abbas Shafiee、Mohsen Amini

  DOI：10.1016/j.bmc.2013.01.058

  日期：2013.4

  A series of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and 2-alkylsulfonyl-1H-imidazole derivatives were synthesized. All compounds were tested in human blood assay to determine COX-1 and COX-2 inhibitory potency and selectivity. Among the synthesized compounds, 2-alkylthio series were more potent and selective than 2-sulfonylalkyl derivatives. In molecular modeling, interaction of 2-sulfonylalkyl moiety with Arg120 in COX-1 and an extra hydrogen bond with Tyr341 in COX-2 increased the residence time of ligands in the active site in 2-sulfonylalkyl and 2-alkylthio analogs, respectively. (C) 2013 Elsevier Ltd. All rights reserved.