(2RS)-2-bromo-1-(4-methylsulfonylphenyl)-2-phenyl-1-ethanone | 33512-71-9

• 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: (2RS)-2-bromo-1-(4-methylsulfonylphenyl)-2-phenyl-1-ethanone
• 英文别名: 2-bromo-1-(4''-(methylsulfonyl)phenyl)-2-phenyl-1-ethanone；2-bromo-1-[4-(methylsulfonyl)phenyl]-2-phenylethanone；2-bromo-1-(4-(methylsulfonyl)phenyl)-2-phenylethan-1-one；1-(4-(Methylsulfonyl)phenyl)-2-bromo-2-phenylethanone；2-bromo-1-(4-methylsulfonylphenyl)-2-phenylethanone
• CAS: 33512-71-9
• 化学式: C₁₅H₁₃BrO₃S
• 分子量: 353.236
• InChiKey: JOSXNLMCTDEMRB-UHFFFAOYSA-N

物化性质

• 沸点：
  501.9±50.0 °C(Predicted)
• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：

  (2RS)-2-bromo-1-(4-methylsulfonylphenyl)-2-phenyl-1-ethanone 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,2,2-Trifluoro-1-[5-(4-methanesulfonyl-phenyl)-6-phenyl-3,6-dihydro-2H-pyrazin-1-yl]-ethanone
  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：

  2-phenyl-4'-(methylthio)acetophenone 在 Oxone 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 生成 (2RS)-2-bromo-1-(4-methylsulfonylphenyl)-2-phenyl-1-ethanone
  参考文献：
  名称：

  靶向蝶啶还原酶 1 的抗寄生虫吡咯并嘧啶的基于结构的设计与合成

  摘要：

  非洲人类锥虫病的治疗仍然是撒哈拉以南非洲地区未满足的主要健康需求。涉及新分子目标的方法很重要；蝶啶还原酶 1 (PTR1) 是一种在锥虫属中减少二氢生物蝶呤的酶，已被确定为候选靶标，之前已表明取代的吡咯并 [2,3- d ] 嘧啶是布氏锥虫PTR1 的抑制剂( J. Med. Chem. 2010 , 53 , 221–229)。在本研究中，61 个新的吡咯并 [2,3- d]嘧啶已经制备，设计了 23 种与 PTR1 复合的化合物的新晶体结构，并在屏幕上评估了对 PTR1 的酶抑制活性和体外抗锥虫活性。八种化合物在两个筛选中都具有足够的活性，可以进行体内评估。因此，尽管获得了小鼠 I 期疾病模型中锥虫杀灭活性的证据，但这些化合物对小鼠的毒性太大，无法进一步开发。

  DOI：

  10.1021/jm500483b

文献信息

• Aryl substituted 5,5 fused aromatic nitrogen compounds as
  申请人：Merck Frosst Canada, Inc.

  公开号：US05552422A1

  公开（公告）日：1996-09-03

  The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  该发明涵盖了公式I的新化合物，以及一种治疗环氧合酶-2介导疾病的方法，包括向需要该治疗的患者施用公式I化合物的非毒性治疗有效量。 该发明还涵盖了用于治疗环氧合酶-2介导疾病的某些药物组合，其中包括公式I的化合物。
• Emergent antibacterial activity of<i>N</i>-(thiazol-2-yl)benzenesulfonamides in conjunction with cell-penetrating octaarginine
  作者：Poonam Ratrey、Amarjyoti Das Mahapatra、Shiny Pandit、Murtuza Hadianawala、Sasmita Majhi、Abhijit Mishra、Bhaskar Datta

  DOI：10.1039/d1ra03882f

  日期：——

  Hybrid antimicrobials that combine the effect of two or more agents represent a promising antibacterial therapeutic strategy. In this work, we have synthesized N-(4-(4-(methylsulfonyl)phenyl)-5-phenylthiazol-2-yl)benzenesulfonamide derivatives that combine thiazole and sulfonamide, groups with known antibacterial activity. These molecules are investigated for their antibacterial activity, in isolation

  结合两种或多种药剂的作用的混合抗菌剂代表了一种有前途的抗菌治疗策略。在这项工作中，我们合成了N -(4-(4-(甲基磺酰基)苯基)-5-苯基噻唑-2-基)苯磺酰胺衍生物，该衍生物结合了噻唑和磺酰胺，这些基团具有已知的抗菌活性。研究这些分子的抗菌活性，分离并与细胞穿透肽八精氨酸复合。几种合成的化合物对革兰氏阴性和革兰氏阳性细菌均显示出有效的抗菌活性。具有 4-叔丁基和 4-异丙基取代的化合物对多种菌株表现出有吸引力的抗菌活性。异丙基取代的衍生物显示出 3.9 μg mL 的低 MIC-1对金黄色葡萄球菌和木糖氧化酵母菌. 药物-肽复合物、单独药物和单独肽的比较抗菌行为表明药物-肽复合物的独特作用模式，而不是其组成成分的简单总和。从抗菌行为与合成中间体-肽复合物的比较中可以看出药物-肽复合物的特异性。八精氨酸-药物复合物对细菌细胞表现出更快的杀伤动力学，在细菌细胞膜上产生孔，对人红细胞的溶血活
• [EN] ARYL SUBSTITUTED 5,5 FUSED AROMATIC NITROGEN COMPOUNDS AS ANTI-INFLAMMATORY AGENTS<br/>[FR] COMPOSES AZOTES AROMATIQUES CONDENSES 5,5-ARYL-SUBSTITUES UTILISES COMME AGENTS ANTI-INFLAMMATOIRES
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1996021667A1

  公开（公告）日：1996-07-18

  (EN) The invention encompasses the novel compound of formula (I) as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of formula (I). The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of formula (I).(FR) On décrit un nouveau composé de formule (I), ainsi qu'un procédé, permettant de traiter des affections médiées par la cyclo-oxygénase-2, qui consiste à administrer à un patient nécessitant un tel traitement une quantité non toxique et thérapeutiquement efficace d'un composé de formule (I). On décrit aussi certaines compositions pharmaceutiques, contenant des composés de formule (I), qui permettent de traiter ces affections médiées par la cyclo-oxygénase-2.

  该发明涵盖了式（I）的新化合物，以及治疗环氧合酶-2介导的疾病的方法，包括向需要此类治疗的患者给予化合物式（I）的非毒性治疗有效量。该发明还涵盖了某些治疗环氧合酶-2介导的疾病的药物组合物，其中包括化合物式（I）。
• 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.
• 1,2-Diaryl-1-ethanone and pyrazolo [4,3-c] quinoline-4-one as novel selective cyclooxygenase-2 inhibitors
  作者：Bipul Baruah、Kavitha Dasu、Balasubramanian Vaitilingam、Akhila Vanguri、Seshagiri Rao Casturi、Koteswar Rao Yeleswarapu

  DOI：10.1016/j.bmcl.2003.10.052

  日期：2004.1

  Novel 1,2-diaryl-1-ethanone I and pyrazolo [4,3-c] quinoline-4-one 2, with pharmacophores different from the known COX inhibitors were identified as selective COX-2 inhibitors. The communication briefly describes SAR of both the series. (C) 2003 Elsevier Ltd. All rights reserved.