2',4'-dihydroxy-2,4,5-trimethoxychalcone

• 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: 2',4'-dihydroxy-2,4,5-trimethoxychalcone
• 英文别名: 2',4'-Dihydroxy-2,4,5-trimethoxy-(carbonyl-¹⁴C)chalcon；(E)-1-(2,4-dihydroxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: AZNIBGZCLFHAFA-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 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：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2',4'-dihydroxy-2,4,5-trimethoxychalcone 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以52%的产率得到2-(2,4,5-Trimethoxyphenyl)-7-hydroxy chromen-4-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
• 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 2',4'-dihydroxy-2,4,5-trimethoxychalcone
  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

• Solid-phase synthesis of 2′-hydroxychalcones. Effects on cell growth inhibition, cell cycle and apoptosis of human tumor cell lines
  作者：Marta Perro Neves、Sara Cravo、Raquel T. Lima、M. Helena Vasconcelos、M. São José Nascimento、Artur M.S. Silva、Madalena Pinto、Honorina Cidade、Arlene G. Corrêa

  DOI：10.1016/j.bmc.2011.11.042

  日期：2012.1

  Thirty-one 2′-hydroxychalcones were prepared via solid-phase synthesis by base-catalyzed aldol condensation of substituted 2′-hydroxyacetophenones and benzaldehydes. Chalcones were tested for their growth inhibitory activity in three human tumor cell lines (MCF-7, NCI-H460 and A375-C5) using the SRB assay. Results revealed that several of the tested compounds caused a pronounced dose-dependent growth

  通过固相合成，通过碱催化取代的2'-羟基苯乙酮和苯甲醛的醛醇缩合反应制备了31个2'-羟基查耳酮。使用SRB分析法测试了Chalcones在三种人类肿瘤细胞系（MCF-7，NCI-H460和A375-C5）中的生长抑制活性。结果显示，在低微摩尔范围内，几种测试化合物对所研究的肿瘤细胞系产生了明显的剂量依赖性生长抑制作用。为了进一步了解这类化合物的细胞作用机理，还研究了它们对细胞周期谱以及诱导细胞凋亡的影响。通常，测试的查耳酮干扰细胞周期特征并增加凋亡的MCF-7细胞的百分比。