3-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl)prop-2-en-1-one | 819792-63-7

• 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: 3-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl)prop-2-en-1-one
• 英文别名: 1-[4-(Methanesulfonyl)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one；3-(4-methoxyphenyl)-1-(4-methylsulfonylphenyl)prop-2-en-1-one
• CAS: 819792-63-7
• 化学式: C₁₇H₁₆O₄S
• 分子量: 316.378
• InChiKey: OLMRNLAECSKIAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl)prop-2-en-1-one 、 4-(4-氯苯基)-氨基脲 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以45%的产率得到N-(4-chlorophenyl)-5-(4-methoxyphenyl)-3-[4-(methylsulfonylphenyl)]-4,5-dihydro-1H-pyrazole-1-carboxamide
  参考文献：
  名称：

  Discovery and structure activity relationships of 2-pyrazolines derived from chalcones from a pest management perspective

  摘要：

  Synthesis of chalcones and 2-pyrazoline derivatives has been an active field of research due to the established pharmacological effects of these compounds. In this study, a series of chalcone (1a-i), 2-pyrazoline-1-carbothioamides (2a-i), and 2-pyrazoline-1-carboxamide derivatives (3a-g) were synthesized and screened for their potential pesticide activities. The proposed structures of all the synthesized compounds were confirmed using the elemental analysis, UV, IR, H-1-NMR, and mass spectroscopy. Among the total of 25 tested compounds, compounds 1g and 2a and 2e with Biting Deterrence Index (BDI) values of 0.85, 0.83, and 0.8, respectively, at 25 nmol/cm(2) showed the highest biting deterrent activity against Aedes aegypti, which was comparable to N,N-diethyl-3-methylbenzamide (DEET). Compounds 1g, 2a and 2e were subsequently tested in human-based repellent bioassays, and they showed MED (minimum effective dose) values of 0.375, 0.094, and 0.375 mg/cm(2), respectively. Compound 1e was the most toxic compound (LC50 = 2.58 ppm), followed by 1f (LC50 = 5.69 ppm) and 2g (LC50 = 15.14 ppm), against 1-day-old Ae. aegypti larvae. Compounds 1f and 2h 1f and 2h showed the greatest growth inhibition against Colletotrichum gloeosporioides (97.6 and 98.5 %, respectively) at the lowest dose (0.3 mu M), which was greater antifungal activity than with standard commercial fungicides captan and azoxystrobin. Compounds 2d, 2g and 2h produced 79.5, 98.3, and 82.3 % growth inhibition, respectively, at 30.0 mu M against Botrytis cinerea, which was similar to captan in the antifungal activity. The active fungicidal compounds (2d, 2g, and 2h) were weaky phytotoxic, with little or no phytotoxicity at concentrations that were fungitoxic. Compound 2h stimulated the growth of Lemma paucicostata at concentrations that are fungitoxic to several plant pathogens.

  DOI：

  10.1007/s00044-015-1415-8
• 作为产物：
  描述：

  4-甲砜基苯乙酮 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(4-methoxyphenyl)-1-(4-(methylsulfonyl)phenyl)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 and biological evaluation of N-substituted-3,5-diphenyl-2-pyrazoline derivatives as cyclooxygenase (COX-2) inhibitors
  作者：Rossella Fioravanti、Adriana Bolasco、Fedele Manna、Francesca Rossi、Francisco Orallo、Francesco Ortuso、Stefano Alcaro、Roberto Cirilli

  DOI：10.1016/j.ejmech.2010.10.005

  日期：2010.12

  Eighteen new 1-N-substituted-3,5-diphenyl-2-pyrazoline derivatives have been synthesized and cyclooxygenase (COX-1 and COX-2) inhibitory activities have been evaluated. The results of these biological assays showed that all of new derivatives are not endowed with improved anti-inflammatory activity against COX-1, but some of them showed a good activity against COX-2. To evaluate the binding mode of the most significative compounds (2d, 2f, 2g and 2k) docking studies were carried out. These studies confirmed biological data, in fact these compounds were able to fit into the active site of COX-2. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 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.
• Discovery and structure activity relationships of 2-pyrazolines derived from chalcones from a pest management perspective
  作者：Bedia Koçyiğit-Kaymakçıoğlu、Nagihan Beyhan、Nurhayat Tabanca、Abbas Ali、David E. Wedge、Stephen O. Duke、Ulrich R. Bernier、Ikhlas A. Khan

  DOI：10.1007/s00044-015-1415-8

  日期：2015.10

  Synthesis of chalcones and 2-pyrazoline derivatives has been an active field of research due to the established pharmacological effects of these compounds. In this study, a series of chalcone (1a-i), 2-pyrazoline-1-carbothioamides (2a-i), and 2-pyrazoline-1-carboxamide derivatives (3a-g) were synthesized and screened for their potential pesticide activities. The proposed structures of all the synthesized compounds were confirmed using the elemental analysis, UV, IR, H-1-NMR, and mass spectroscopy. Among the total of 25 tested compounds, compounds 1g and 2a and 2e with Biting Deterrence Index (BDI) values of 0.85, 0.83, and 0.8, respectively, at 25 nmol/cm(2) showed the highest biting deterrent activity against Aedes aegypti, which was comparable to N,N-diethyl-3-methylbenzamide (DEET). Compounds 1g, 2a and 2e were subsequently tested in human-based repellent bioassays, and they showed MED (minimum effective dose) values of 0.375, 0.094, and 0.375 mg/cm(2), respectively. Compound 1e was the most toxic compound (LC50 = 2.58 ppm), followed by 1f (LC50 = 5.69 ppm) and 2g (LC50 = 15.14 ppm), against 1-day-old Ae. aegypti larvae. Compounds 1f and 2h 1f and 2h showed the greatest growth inhibition against Colletotrichum gloeosporioides (97.6 and 98.5 %, respectively) at the lowest dose (0.3 mu M), which was greater antifungal activity than with standard commercial fungicides captan and azoxystrobin. Compounds 2d, 2g and 2h produced 79.5, 98.3, and 82.3 % growth inhibition, respectively, at 30.0 mu M against Botrytis cinerea, which was similar to captan in the antifungal activity. The active fungicidal compounds (2d, 2g, and 2h) were weaky phytotoxic, with little or no phytotoxicity at concentrations that were fungitoxic. Compound 2h stimulated the growth of Lemma paucicostata at concentrations that are fungitoxic to several plant pathogens.
• 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-(