(E)-1-(3-Triflurophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

• 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: (E)-1-(3-Triflurophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-[3-(trifluoromethyl)phenyl]-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₉H₁₇F₃O₄
• 分子量: 366.337
• InChiKey: WQBBMSPKGIVDDX-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  顺式-2,4,5-三甲氧基-1-丙烯基苯 在 potassium permanganate 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-(3-Triflurophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure–activity relationship

  摘要：

  2,4,5-Trimethoxy chalcones and analogues were synthesized from asaronaldehyde derived from beta-asarone. These novel compounds when tested against three human tumour cell lines (MCF-7, SW-982 and HeLa) using MTT assay, revealed that chalcones possessing electron donor groups in para position to carbonyl moiety of phenyl ring A, showed better inhibitory activity (2, 3, 4, 6, 7, 10, 17). When evaluated for antioxidant activities, compound 15 exhibited better free radical scavenging property in DPPH assay while compounds 2, 3, 5, 7, 9, 10, 11, 16, and 18 showed significant NO scavenging activity. All compounds exhibited very good phenyl hydrazine induced haemolysis of erythrocytes in phenylhydrazine assay. Structure activity relationship (SAR) study using in-silico analysis matched well with in-vitro tumour cell inhibitory activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.018

文献信息

• The synthesis and effect of fluorinated chalcone derivatives on nitric oxide production
  作者：Javier Rojas、Miguel Payá、José N Dominguez、M Luisa Ferrándiz

  DOI：10.1016/s0960-894x(02)00317-7

  日期：2002.8

  Dimethoxy- and trimethoxychalcone derivatives, with various patterns of fluorination, were synthesized and evaluated for their influence on nitric oxide production. Some of them, chalcones 1, 5, 7, 10, 11 and 17, inhibited NO production with an IC50 in the submicromolar range; 17 is especially noteworthy because of its potency (IC50 30 nM). These effects were not the consequence of a direct inhibitory action on enzyme activity but the inhibition of enzyme expression. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure–activity relationship
  作者：Suvarna Shenvi、Krishna Kumar、Kaushik S. Hatti、K. Rijesh、Latha Diwakar、G. Chandrasekara Reddy

  DOI：10.1016/j.ejmech.2013.01.018

  日期：2013.4

  2,4,5-Trimethoxy chalcones and analogues were synthesized from asaronaldehyde derived from beta-asarone. These novel compounds when tested against three human tumour cell lines (MCF-7, SW-982 and HeLa) using MTT assay, revealed that chalcones possessing electron donor groups in para position to carbonyl moiety of phenyl ring A, showed better inhibitory activity (2, 3, 4, 6, 7, 10, 17). When evaluated for antioxidant activities, compound 15 exhibited better free radical scavenging property in DPPH assay while compounds 2, 3, 5, 7, 9, 10, 11, 16, and 18 showed significant NO scavenging activity. All compounds exhibited very good phenyl hydrazine induced haemolysis of erythrocytes in phenylhydrazine assay. Structure activity relationship (SAR) study using in-silico analysis matched well with in-vitro tumour cell inhibitory activity. (C) 2013 Elsevier Masson SAS. All rights reserved.