5,5'-diallyl-(1,1'-biphenyl)-2,2',3-triol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5'-diallyl-(1,1'-biphenyl)-2,2',3-triol
• 英文别名: 3-(2-Hydroxy-5-prop-2-enylphenyl)-5-prop-2-enylbenzene-1,2-diol；3-(2-hydroxy-5-prop-2-enylphenyl)-5-prop-2-enylbenzene-1,2-diol
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: LIGYYTGBJGANPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  厚朴酚 在 2-碘酰基苯甲酸 、 sodium dithionite 作用下， 以 甲醇 为溶剂， 以16.2 %的产率得到5,5'-diallyl-(1,1'-biphenyl)-2,2',3-triol
  参考文献：
  名称：

  厚朴酚衍生物作为乳腺癌抗性蛋白 (BCRP/ABCG2) 的特异性非细胞毒性抑制剂

  摘要：

  乳腺癌耐药蛋白（BCRP/ABCG2）转运蛋白介导多种抗肿瘤药物的流出，在与癌症相关的多药耐药性中发挥着核心作用。由于缺乏使用特定 ABCG2 抑制剂的成功临床试验，人们迫切需要寻找新的化合物来满足这一关键需求。在这项工作中，测试了一系列 13 种厚朴酚衍生物作为 ABCG2 抑制剂。只有两种化合物，衍生物和，分别表现出部分和完全的ABCG2抑制作用。这种抑制对 ABCG2 是选择性的，因为 13 种化合物中没有一种既不抑制 P-糖蛋白也不抑制 MRP1。两种抑制剂 ( 和 ) 均不被 ABCG2 转运，即使在高浓度（高达 100 µM）下也表现出较低的细胞毒性。考虑到细胞毒性 (IG) 和 ABCG2 抑制效力 (IC) 之间的比率，显示出治疗比率 (TR) 高于观察到的水平（分别为 10.5 ± 1.6），成为该系列中最有前途的化合物。该衍生物表现出底物依赖性和混合型抑制。化合物对 ABCG2

  DOI：

  10.1016/j.bioorg.2024.107283

文献信息

• Identification by Inverse Virtual Screening of magnolol-based scaffold as new tankyrase-2 inhibitors
  作者：Simone Di Micco、Luana Pulvirenti、Ines Bruno、Stefania Terracciano、Alessandra Russo、Maria C. Vaccaro、Dafne Ruggiero、Vera Muccilli、Nunzio Cardullo、Corrado Tringali、Raffaele Riccio、Giuseppe Bifulco

  DOI：10.1016/j.bmc.2018.06.019

  日期：2018.8

  The natural product magnolol (1) and a selection of its bioinspired derivatives 2-5, were investigated by Inverse Virtual Screening in order to identify putative biological targets from a panel of 308 proteins involved in cancer processes. By this in silico analysis we selected tankyrase-2 (TNKS2), casein kinase 2 (CK2) and bromodomain 9 (Brd9) as potential targets for experimental evaluations. The Surface Plasmon Resonance assay revealed that 3-5 present a good affinity for tankyrase-2, and, in particular, 3 showed an antiproliferative activity on A549 cells higher than the well-known tankyrase-2 inhibitor XAV939 used as reference compound.
• Chemoenzymatic Synthesis and α-Glucosidase Inhibitory Activity of Dimeric Neolignans Inspired by Magnolol
  作者：Luana Pulvirenti、Vera Muccilli、Nunzio Cardullo、Carmela Spatafora、Corrado Tringali

  DOI：10.1021/acs.jnatprod.7b00250

  日期：2017.5.26

  A chemoenzymatic synthesis of a small library of dimeric neolignans inspired by magnolol (1) is reported. The 2-iodoxybenzoic acid (IBX)-mediated regioselective orthohydroxylation of magnolol is described, affording the bisphenols 6 and 7. Further magnolol analogues (12, 13, 15-17, 19-23) were obtained from eugenol (3), tyrosol (4), and homovanillic alcohol (5), through horseradish peroxidase (HRP)-mediated oxidative coupling and regioselective orthohydroxylation or ortho-demethylation in the presence of MX, followed by reductive treatment with Na2S2O4. A chemoselective protection/deprotection of the alcoholic group of 4 and 5 was carried out by lipase-mediated acetylation/deacetylation. The dimeric neolignans, together with 1 and honokiol (2), were evaluated as inhibitors of yeast a-glucosidase, in view of their possible utilization and optimization as antidiabetic drugs. The synthetic analogues of magnolol showed a strong inhibitory activity with IC50 values in the range 0.15-4.1 mu M, much lower than those of honokiol and the reference compounds quercetin and acarbose. In particular, a very potent inhibitory activity, with an IC50 of 0.15 mu M, was observed for 1,1'-dityrosol-8,8'-diacetate (15), and comparable inhibitory activities were also shown by bisphenols 6 (0.49 mu M), 13 (0.50 mu M), and 22 (0.86 mu M). A kinetic study showed that 15 acts as a competitive inhibitor, with a K-i value of 0.86 mu M.