2'-hydroxy-3,4-dimethoxy-4'-O-prenylchalcone | 1243560-89-5

• 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'-hydroxy-3,4-dimethoxy-4'-O-prenylchalcone
• 英文别名: (E)-3-(3,4-dimethoxyphenyl)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]prop-2-en-1-one；2''-Hydroxy-3,4-dimethoxy-4''-O-prenylchalcone；(E)-3-(3,4-dimethoxyphenyl)-1-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]prop-2-en-1-one
• CAS: 1243560-89-5
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: BOSNJXXUKJSFDF-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 8.0h， 生成 2'-hydroxy-3,4-dimethoxy-4'-O-prenylchalcone
  参考文献：
  名称：

  Structure–activity relationships of chalcone analogs as potential inhibitors of ADP- and collagen-induced platelet aggregation

  摘要：

  In an effort to develop potent antiplatelet agents, 12 O-prenylated (2-13) and 10 O-allylated (14-23) chalcones were synthesized and screened for in vitro inhibitory effects on aggregation of washed rabbit platelets induced by ADP (20 mu M) and collagen (10 mu g/mL). In addition, the platelet aggregation activity of previously synthesized Mannich bases of heterocyclic chalcones (MBHC) (24-62) was evaluated. The preliminary structure-activity relationships suggested that the antiplatelet activity was governed to a great extent by the presence of a pyridyl ring-B and a hydroxy group at position C-3' in ring-A of the MBHC templates. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.08.004

文献信息

• Design, synthesis, and biological evaluation of prenylated chalcones as 5-LOX inhibitors
  作者：Nimmanapalli P. Reddy、Polamarasetty Aparoy、T. Chandra Mohan Reddy、Chandrani Achari、P. Ramu Sridhar、Pallu Reddanna

  DOI：10.1016/j.bmc.2010.06.107

  日期：2010.8

  mono- and di-O-prenylated chalcone derivatives were designed on the basis of a homology derived molecular model of 5-lipoxygenase (5-LOX). The compounds were docked into 5-LOX active site and the binding characteristics were quantified using LUDI. To verify our theoretical assumption, the molecules were synthesized and tested for their 5-LOX inhibitory activities. The synthesis was carried out by Claisen–Schmidt

  基于5-脂氧合酶（5-LOX）的同源性衍生分子模型，设计了十种新颖的单-和二-O-烯丙基化查尔酮衍生物。将化合物对接至5-LOX活性位点，并使用LUDI定量结合特征。为了验证我们的理论假设，对分子进行了合成并测试了其5-LOX抑制活性。通过单-和二-O-烯丙基化的苯乙酮与适当的醛的克莱森-施密特缩合反应进行合成。5-LOX体外抑制试验显示，二-O-异戊烯化查耳酮的功效比其单-O-异戊烯化查耳酮类似物更高。化合物5e对IC 50表现出良好的抑制作用为4μM。计算的结合能和LUDI得分的总体趋势与实验数据在质量上吻合良好。此外，化合物5e中显示了强的抗增殖作用（GI 50对乳腺癌细胞系在9μM），MCF-7。