(E)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]-3-(4-methoxyphenyl)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-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 2'-hydroxy-4-methoxy-4'-prenyloxychalcone；2'-hydroxy-4-methoxy-4'-O-prenylchalcone；Substituted chalcone, 5c；(E)-1-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: NPUSLOJIVPNJCQ-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one 在 乙酸酐 、 N,N-二甲基苯胺 作用下， 反应 4.0h， 以6.5%的产率得到2'-hydroxy-4-methoxy-4'',4'',5''-trimethyldihydrofurano(2'',3'':4',3')chalcone
  参考文献：
  名称：

  Islam, Azizul; Anam, M. Rafiqul; Hossain, M. Amzad, Pakistan Journal of Scientific and Industrial Research, 1994, vol. 37, # 1-2, p. 29 - 32

  摘要：

  DOI：
• 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 (E)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one
  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。
• Chalcones: A Valid Scaffold for Monoamine Oxidases Inhibitors
  作者：Franco Chimenti、Rossella Fioravanti、Adriana Bolasco、Paola Chimenti、Daniela Secci、Francesca Rossi、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro

  DOI：10.1021/jm801590u

  日期：2009.5.14

  A large series of substituted chalcones have been synthesized and tested in vitro for their ability to inhibit human monoamine oxidases A and B (hMAO-A and hMAO-B). While all the compounds showed hMAO-B selective activity in the micro- and nanomolar ranges, the best results were obtained in the presence of chlorine and hydroxyl or methoxyl substituents. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAO-B, molecular modeling studies were carried out on new, high resolution, hMAO-B crystallographic structures. For the only compound that also showed activity against hMAO-A as well as low selectivity, the molecular modeling study was also performed on the hMAO-A crystallographic structure. The docking technique provided new insight on the inhibition mechanism and the rational drug design of more potent/selective hMAO inhibitors based on the chalcone scaffold.