1-(3,4-Dimethoxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one | 121646-12-6

• 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-(3,4-Dimethoxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
• CAS: 121646-12-6
• 化学式: C₁₈H₁₈O₃S
• 分子量: 314.405
• InChiKey: FWAAFYDERPUUOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,4-Dimethoxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-[1-{3-(3,4-dimethoxyphenyl)-5-(4-methylthiophenyl)-4,5-dihydro-1H-pyrazolyl}]-4-(4-nitrophenyl)[1,3]thiazole
  参考文献：
  名称：

  Synthesis, antimicrobial and antioxidant activities of 2-[1-{3,5-diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]-thiazoles

  摘要：

  In this study, various substituted chalcones, prepared by condensing substituted acetophenones with substituted aldehydes/arylfurfurals, were treated with thiosemicarbazide in basic media to produce 1-thiocarbonyl-3,5-disubstituted pyrazolines which on further reaction with substituted phenacyl bromides afforded the title compounds in good yield. Structures of the newly synthesized compounds were assigned on the basis of elemental analyses, IR, H-1 NMR, and mass spectral studies. The newly synthesized compounds were tested for their in vitro antibacterial and antifungal activities against a variety of microorganisms and antioxidant activities by diphenylpicrylhydrazyl radical scavenging assay. Among the derivatives, compounds 3b, 3e, 6a, and 6h were identified as potent antioxidants. Compounds 3d, 3e, and 6a-f have emerged as the most promising antimicrobial agents displaying the maximum activity against all the tested microorganisms.

  DOI：

  10.1007/s00044-012-0154-3
• 作为产物：
  描述：

  4-(甲基巯基)苯甲醛 、 3,4-二甲氧基苯乙酮 在 alkali hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-(3,4-Dimethoxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  一种用于吡唑啉区域选择性合成的权宜之计、一锅法、逐步顺序方法

  摘要：

  通过使用查耳酮和吡啶-4-碳酰肼的单锅、逐步、顺序方法，描述了一种合成吡唑啉/吡唑系吡啶基甲酮的有效方法。

  DOI：

  10.1177/1747519820977165

文献信息

• Novel 1,3,5-triphenyl-2-pyrazolines as anti-infective agents
  作者：P.M. Sivakumar、S. Prabhu Seenivasan、Vanaja Kumar、Mukesh Doble

  DOI：10.1016/j.bmcl.2010.03.083

  日期：2010.5

  Sixteen 1,3,5-triphenyl-2-pyrazolines were synthesized and their anti-infective activities (against Mycobacterium tuberculosis H(37)Rv, six bacterial and four fungal strains) were tested. Only compound with SO(2)CH(3) in the para position of the A-ring was active against the tubercular strain at 100 mu g/ml concentration. All compounds showed good anti infective activity against Escherichia coli and poor activity against Staphylococcus aureus. Compounds 4, 12, 13 and 14 exhibited reasonable activity against all the organisms tested (<0.309 mu M except against S. aureus. The activity of these compounds correlated with their lipophilic/hydrophilic nature. Compounds 4, 10 and 16 showed very good activity (>88% reduction) against four fungi studied at 2 mg/ml. All these compounds possess halogen substitutions. Compound 11 showed very high activity (>90%) against three fungi. Majority of the compounds showed more than 90% inhibition against one or two fungi. Since pyrazolines are reported to inhibit the activity of p-glycoprotein, they may prevent drug resistance developed by microorganism. (C) 2010 Elsevier Ltd. All rights reserved.
• An expedient, one-pot, stepwise sequential approach for the regioselective synthesis of pyrazolines
  作者：Suresh Ganesan、Muniraj Sarangapani、Mukesh Doble

  DOI：10.1177/1747519820977165

  日期：2021.3

  An efficient approach for the synthesis of pyrazoline/pyrazole-tethered pyridinyl methanones is described via a one-pot, stepwise, sequential methodology using chalcones and pyridine-4-carbohydrazi...

  通过使用查耳酮和吡啶-4-碳酰肼的单锅、逐步、顺序方法，描述了一种合成吡唑啉/吡唑系吡啶基甲酮的有效方法。
• Synthesis, antimicrobial and antioxidant activities of 2-[1-{3,5-diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]-thiazoles
  作者：Prajwal Lourdes Lobo、Boja Poojary、Manjunatha Kumsi、Vinaya Chandra、Nalilu Sucheta Kumari、K. R. Chandrashekar

  DOI：10.1007/s00044-012-0154-3

  日期：2013.4

  In this study, various substituted chalcones, prepared by condensing substituted acetophenones with substituted aldehydes/arylfurfurals, were treated with thiosemicarbazide in basic media to produce 1-thiocarbonyl-3,5-disubstituted pyrazolines which on further reaction with substituted phenacyl bromides afforded the title compounds in good yield. Structures of the newly synthesized compounds were assigned on the basis of elemental analyses, IR, H-1 NMR, and mass spectral studies. The newly synthesized compounds were tested for their in vitro antibacterial and antifungal activities against a variety of microorganisms and antioxidant activities by diphenylpicrylhydrazyl radical scavenging assay. Among the derivatives, compounds 3b, 3e, 6a, and 6h were identified as potent antioxidants. Compounds 3d, 3e, and 6a-f have emerged as the most promising antimicrobial agents displaying the maximum activity against all the tested microorganisms.