2-(4-chlorophenyl)-1-(4-methylsulfanylphenyl)ethanone | 225668-35-9

• 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: 2-(4-chlorophenyl)-1-(4-methylsulfanylphenyl)ethanone
• 英文别名: 2-(4-chlorophenyl)-1-[4-(methylthio)phenyl]-1-ethanone；2-(4-chlorophenyl)-4'-(methylthio)acetophenone
• CAS: 225668-35-9
• 化学式: C₁₅H₁₃ClOS
• 分子量: 276.787
• InChiKey: MMWCHRKSYDTYQU-UHFFFAOYSA-N

物化性质

• 熔点：
  124-127 °C(Solv: hexane (110-54-3))
• 沸点：
  427.7±30.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：

  2-(4-chlorophenyl)-1-(4-methylsulfanylphenyl)ethanone 在 Oxone 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  作为 COX-2 和 β-淀粉样蛋白聚集抑制剂的 5,6-二芳基-1,2,4-三嗪-3-基硫代乙酸酯衍生物的设计、合成和体外研究

  摘要：

  为了寻找新的环氧合酶 (COX)-2 抑制剂来治疗阿尔茨海默病 (AD) 等炎症性疾病，将羧酸乙酯侧链添加到 5-(4-氯苯基)-6-(4-(甲基磺酰基)苯基)-3-(甲硫基)-1,2,4-三嗪（先导化合物 II）通过与 Arg120 相互作用维持对 COX-1 的残留抑制。对 COX-1/COX-2 活性位点的初步分子对接研究确实证实了我们的假设。因此，合成了一系列 5,6-二芳基-1,2,4-三嗪-3-基硫代乙酸乙酯衍生物，并通过 NMR、IR 和 MS 光谱证实了它们的化学结构。进一步的体外 COX-1/COX-2 评估显示化合物 6c（COX-2 IC50 = 10.1 μM，COX-1 IC50 = 88.8 μM）是最具选择性的 COX-2 抑制剂，同时保持对 COX-1 的残留抑制。为了评估它们对 AD 的潜在用途，进行了 β-淀粉样蛋白原纤维形成的体外评估。结果表明，原型化合物

  DOI：

  10.1002/ardp.201400400
• 作为产物：
  描述：

  对氯苯乙酸 在 三氯化铝 、 氯化亚砜 作用下， 反应 3.75h， 生成 2-(4-chlorophenyl)-1-(4-methylsulfanylphenyl)ethanone
  参考文献：
  名称：

  Synthesis of novel substituted diaryl-1,4-diazepines

  摘要：

  DOI：

  10.1007/s10593-006-0178-z

文献信息

• Phenylpyridazine compounds and medicines containing the same
  申请人：Kowa Co., Ltd.

  公开号：US06664256B1

  公开（公告）日：2003-12-16

  Phenylpyridazine compounds represented by the following formula (I): are provided, wherein R1, R2, R3, R4, and n are as defined herein having excellent inhibitory activity against interleukin-1&bgr; production, and useful in the treatment of prevention of diseases caused by stimulation of interleukin-1&bgr; production, such as immune system diseases, inflammatory diseases, and ischemic diseases.

  以下公式（I）所代表的苯基吡啶化合物提供，其中R1、R2、R3、R4和n如本文所定义，具有出色的抑制性活性，可用于治疗或预防由白细胞介素-1β产生刺激引起的疾病，如免疫系统疾病、炎症性疾病和缺血性疾病。
• Pyridazine compounds and compositions containing the same
  申请人：Kowa Co., Ltd.

  公开号：US06348468B1

  公开（公告）日：2002-02-19

  This invention relates to pyridazine derivatives represented by the formula (1): wherein R1 represents a (substituted) aryl group, R2 represents a phenyl group substituted at 4-position by a lower alkoxyl group or a lower alkylthio group, R3 represents a lower alkoxyl group, a halogenated lower alkyl group, a lower cycloalkyl group, a (subsituted) aryl group, a (substituted) aryloxy group, a (substituted) nitrogen-containing heterocyclic ring residue, a (substituted) aminocarbonyl group or a lower alkylcarbonyl group, A represents a single bond, a lower alkylene group or a lower alkenylene group, X represents O or S, and the dashed line indicates that the carbon-carbon bond between the 4-position and the 5-position is a single bond or a double bond, or salts thereof; and also to medicines containing them as effective ingredients. These compounds have excellent inhibitory activity against interleukin-1&bgr; production, and are useful as preventives and therapeutics for immune system diseases, inflammatory diseases, ischemic diseases and the like.

  这项发明涉及由式（1）表示的吡啶嗪衍生物： 其中R1代表（取代的）芳基，R2代表在4位被低烷氧基或低烷硫基取代的苯基，R3代表低烷氧基、卤代低烷基、低环烷基、（取代的）芳基、（取代的）芳氧基、（取代的）含氮杂环环残基、（取代的）氨基羰基或低烷基羰基，A代表单键、低烷基烯基或低烷烯基，X代表O或S，虚线表示4位和5位之间的碳-碳键为单键或双键，或其盐；以及含有它们作为有效成分的药物。这些化合物对白细胞介素-1β的产生具有出色的抑制活性，并可用作免疫系统疾病、炎症性疾病、缺血性疾病等的预防和治疗药物。
• Synthesis, docking simulation, biological evaluations and 3D-QSAR study of 5-Aryl-6-(4-methylsulfonyl)-3-(metylthio)-1,2,4-triazine as selective cyclooxygenase-2 inhibitors
  作者：Hamid Irannejad、Abbas Kebriaieezadeh、Afshin Zarghi、Farhad Montazer-Sadegh、Abbas Shafiee、Amir Assadieskandar、Mohsen Amini

  DOI：10.1016/j.bmc.2013.12.002

  日期：2014.1

  hence could be considered as a promising lead candidate for further drug development. Furthermore, the affinity data of these compounds were rationalized through enzyme docking simulation and 3D-QSAR study by k-Nearest Neighbour Molecular Field Analysis.

  合成了一系列的5-芳基-6-（4-甲基磺酰基）-3-（甲硫基）-1，2，4-三嗪衍生物，它们具有抑制COX-1 / COX-2的活性以及体内抗炎作用。并评估了镇痛效果。所有化合物均显示出对COX-2的强抑制作用，IC 50值在0.1–0.2μM的范围内，并且在大多数情况下，在剂量为3和6 mg / kg时，其消炎和镇痛作用均比消炎痛强。其中，5-（4-氯苯基）-6-（4-（甲基磺酰基）苯基）-3-（甲硫基）-1,2,4-三嗪（9c）是最有效和选择性最强的COX-2化合物。其选择性指数395与塞来昔布相当（SI = 405）。评估9c的抗炎和镇痛作用与吲哚美辛相比，它具有更高的药效，因此可以被认为是进一步开发药物的有前途的候选药物。此外，这些化合物的亲和力数据通过酶对接模拟和k-最近邻分子场分析法进行的3D-QSAR研究得到了合理化。
• Synthesis, antileukemic and antiplatelet activities of 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines
  作者：R. Ramajayam、Rajani Giridhar、M.R. Yadav、R. Balaraman、Hakim Djaballah、David Shum、Constantin Radu

  DOI：10.1016/j.ejmech.2007.11.023

  日期：2008.9

  The synthesis, antileukemic and antiplatelet activity evaluation of 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines are described. In general, it was found that compound 17o showed moderate antileukemic activity against MOLT3 human leukemic cancer cell lines. An arachidonic acid induced platelet aggregation effect on washed rat platelets was studied. Compound 17i was found to be the most potent. The antiplatelet

  描述了2,3-二芳基-6,7-二氢-5H-1,4-二氮杂卓的合成，抗白血病和抗血小板活性的评价。通常，发现化合物17o显示出对MOLT3人白血病癌细胞系的中等抗白血病活性。研究了花生四烯酸对洗涤过的大鼠血小板的血小板聚集作用。发现化合物17i是最有效的。抗血小板特性可以通过干扰花生四烯酸途径来介导。
• Novel pyridazine derivatives and medicines containing the same as effective ingredients
  申请人：Ohkuchi Masao

  公开号：US20050267113A1

  公开（公告）日：2005-12-01

  This invention relates to pyridazine derivatives represented by the formula (1): wherein R 1 represents a (substituted) aryl group, R 2 represents a phenyl group substituted at 4 -position by a lower alkoxyl group or a lower alkylthio group, R 3 represents a lower alkoxyl group, a halogenated lower alkyl group, a lower cycloalkyl group, a (subsituted) aryl group, a (substituted) aryloxy group, a (substituted) nitrogen-containing heterocyclic ring residue, a (substituted) aminocarbonyl group or a lower alkylcarbonyl group, A represents a single bond, a lower alkylene group or a lower alkenylene group, X represents O or S, and the dashed line indicates that the carbon-carbon bond between the 4 -position and the 5 -position is a single bond or a double bond, or salts thereof; and also to medicines containing them as effective ingredients. These compounds have excellent inhibitory activity against interleukin- 1 β production, and are useful as preventives and therapeutics for immmune system diseases, inflammatory diseases, ischemic diseases and the like.

  本发明涉及由式（1）表示的吡嗪衍生物：其中R1表示（取代）芳基基团，R2表示在4-位被低烷氧基基团或低烷硫基基团取代的苯基基团，R3表示低烷氧基基团、卤代低烷基基团、低环烷基基团、（取代）芳基基团、（取代）芳氧基基团、（取代）含氮杂环环残基、（取代）氨基甲酰基或低烷基甲酰基，A表示单键、低烷基亚ethylene基或低烷基亚烯基，X表示O或S，虚线表示4-位和5-位之间的碳-碳键为单键或双键，或其盐；以及包含它们作为有效成分的药物。这些化合物对白细胞介素-1β的产生有出色的抑制活性，并且可用作免疫系统疾病、炎症性疾病、缺血性疾病等的预防和治疗。