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.
• Magnolol derivatives as specific and noncytotoxic inhibitors of breast cancer resistance protein (BCRP/ABCG2)
  作者：Isadora da Silva Zanzarini、Diogo Henrique Kita、Gustavo Scheiffer、Kelly Karoline dos Santos、Julia de Paula Dutra、Matteo Augusto Pastore、Fabiane Gomes de Moraes Rego、Geraldo Picheth、Suresh V. Ambudkar、Luana Pulvirenti、Nunzio Cardullo、Vivian Rotuno Moure、Vera Muccilli、Corrado Tringali、Glaucio Valdameri

  DOI：10.1016/j.bioorg.2024.107283

  日期：2024.5

  The breast cancer resistance protein (BCRP/ABCG2) transporter mediates the efflux of numerous antineoplastic drugs, playing a central role in multidrug resistance related to cancer. The absence of successful clinical trials using specific ABCG2 inhibitors reveals the urge to identify new compounds to attend this critical demand. In this work, a series of 13 magnolol derivatives was tested as ABCG2

  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