1-[4-(Methanesulfonyl)phenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 819792-82-0

• 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-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(4-methylsulfonylphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 819792-82-0
• 化学式: C₁₉H₂₀O₆S
• 分子量: 376.43
• InChiKey: MJWZMXCOLQYBTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[4-(Methanesulfonyl)phenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 、 4-磺酰胺基苯肼盐酸盐 以 乙醇 、 水 为溶剂， 反应 24.0h， 以69%的产率得到4-[3-(4-methylsulfonylphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of novel triarylpyrazoline derivatives as selective COX-2 inhibitors

  摘要：

  A new series of triarylpyrazoline derivatives 8a-p containing the most important COX-2 pharmacophore (SO2CH3 or/and SO2NH2) were synthesized by reaction of propen-1-one derivatives 6a-h with different phenyl hydrazine hydrochloride derivatives 7a-b in aqueous ethanol. All prepared compounds were evaluated for their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. All compounds were more selective for COX-2 isozyme than COX-1 isozyme and showed good in vivo anti-inflammatory activity. Compounds 8g, 8j and 8o showed the highest anti-inflammatory activity and were less ulcerogenic (Ulcer Index = 6.85, 7.7, 5.92, respectively) than indomethacin (Ulcer Index = 12.3) and comparable to celecoxib (Ulcer Index = 4.85). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.047
• 作为产物：
  描述：

  4-甲砜基苯乙酮 、 3,4,5-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-[4-(Methanesulfonyl)phenyl]-3-(3,4,5-trimethoxyphenyl)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

• Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of novel triarylpyrazoline derivatives as selective COX-2 inhibitors
  作者：Khaled R.A. Abdellatif、Mohamed A. Abdelgawad、Madlen B. Labib、Taha H. Zidan

  DOI：10.1016/j.bmcl.2015.10.047

  日期：2015.12

  A new series of triarylpyrazoline derivatives 8a-p containing the most important COX-2 pharmacophore (SO2CH3 or/and SO2NH2) were synthesized by reaction of propen-1-one derivatives 6a-h with different phenyl hydrazine hydrochloride derivatives 7a-b in aqueous ethanol. All prepared compounds were evaluated for their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. All compounds were more selective for COX-2 isozyme than COX-1 isozyme and showed good in vivo anti-inflammatory activity. Compounds 8g, 8j and 8o showed the highest anti-inflammatory activity and were less ulcerogenic (Ulcer Index = 6.85, 7.7, 5.92, respectively) than indomethacin (Ulcer Index = 12.3) and comparable to celecoxib (Ulcer Index = 4.85). (C) 2015 Elsevier Ltd. 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-(