2,4'-dimethoxy-3',5-dipropyl-1,1'-biphenyl | 1204187-61-0

• 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: 2,4'-dimethoxy-3',5-dipropyl-1,1'-biphenyl
• 英文别名: 2,4'-dimethoxy-5,3'-dipropylbiphenyl；2,4''-Dimethoxy-5,3''-dipropyl-biphenyl；1-methoxy-2-(4-methoxy-3-propylphenyl)-4-propylbenzene
• CAS: 1204187-61-0
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: GLDMMYBVNSMLGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Dimethylhonokiol 在 Lindlar's catalyst 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 2,4'-dimethoxy-3',5-dipropyl-1,1'-biphenyl
  参考文献：
  名称：

  以和厚朴酚为抗增殖剂的双酚新木脂素的合成

  摘要：

  Honokiol (2) 是一种天然双酚新木脂素，具有多种生物学特性，包括抗肿瘤活性。鉴于其对肿瘤细胞的抗增殖和促凋亡活性，一些研究指出 2 作为潜在的抗癌剂。作为对这些研究的进一步贡献，我们在此报告了受和厚朴酚启发的小型双酚新木脂素库的合成及其抗增殖活性的评估。因此，对天然铅进行简单的化学修饰以获得衍生物 3-9；进一步的新木脂素（12a-c、13a-c、14a-c 和 15a）采用 Suzuki-Miyaura 反应合成，从而获得取代模式不同于和厚朴酚的双酚。这些化合物和天然铅对 HCT-116、HT-29、和 PC3 肿瘤细胞系。六个新木脂素对所有细胞系的 GI50 值均低于 2 个。化合物14a、14c和15a是最有效的抗增殖剂，GI50在3.6-19.1 µM范围内，在某些情况下低于抗癌药物5-氟尿嘧啶。对这些新木脂素进行的流式细胞术实验表明，增殖的抑制主要是由于细胞凋亡过程。这

  DOI：

  10.3390/molecules25030733

文献信息

• Synthesis of Tetrahydrohonokiol Derivates and Their Evaluation for Cytotoxic Activity against CCRF-CEM Leukemia, U251 Glioblastoma and HCT-116 Colon Cancer Cells
  作者：Marketa Bernaskova、Nadine Kretschmer、Wolfgang Schuehly、Antje Huefner、Robert Weis、Rudolf Bauer

  DOI：10.3390/molecules19011223

  日期：——

  Biphenyl neolignans such as honokiol and magnolol, which are the major active constituents of the Asian medicinal plant Magnolia officinalis, are known to exert a multitude of pharmacological and biological activities. Among these, cytotoxic and tumor growth inhibitory activity against various tumour cell lines are well-documented. To further elucidate the cytotoxic effects of honokiol derivatives, derivatizations were performed using tetrahydrohonokiol as a scaffold. The derivatizations comprised the introduction of functional groups, e.g., nitro and amino groups, as well as alkylation. This way, 18 derivatives, of which 13 were previously undescribed compounds, were evaluated against CCRF-CEM leukemia cells, U251 glioblastoma and HCT-116 colon cancer cells. The results revealed no significant cytotoxic effects in any of the three tested cell lines at a test concentration of 10 µM.

  二联苯新木脂素类化合物如和厚朴酚和木兰脂素是亚洲药用植物厚朴的主要活性成分,它们具有多种药理和生物活性。其中,对各种肿瘤细胞系的细胞毒性和肿瘤生长抑制活性已有充分研究记录。 为进一步阐明和厚朴酚衍生物的细胞毒性作用,以四氢和厚朴酚为骨架进行了衍生化研究。衍生化包括引入硝基和氨基等官能团以及烷基化。 通过这种方式,对18个衍生物(其中13个为此前未描述的化合物)在CCRF-CEM白血病细胞、U251胶质母细胞瘤和HCT-116结肠癌细胞中进行了评估。结果显示,在10 μM的测试浓度下,这些化合物在三种测试细胞系中均未显示出显著的细胞毒性作用。
• Design and synthesis of ten biphenyl-neolignan derivatives and their in vitro inhibitory potency against cyclooxygenase-1/2 activity and 5-lipoxygenase-mediated LTB4-formation
  作者：Wolfgang Schühly、Antje Hüfner、Eva M. Pferschy-Wenzig、Elke Prettner、Michael Adams、Antje Bodensieck、Olaf Kunert、Asije Oluwemimo、Ernst Haslinger、Rudolf Bauer

  DOI：10.1016/j.bmc.2009.05.018

  日期：2009.7

  A set of ten derivatives of methylhonokiol, an anti-inflammatory active biphenyl-type neolignan from Magnolia grandiflora, has been evaluated for their in vitro cyclooxygenase-1/2 (COX-1/2) inhibitory activity using assays with purified prostaglandin H synthase (PGHS)-1 and PGHS-2 enzymes as well as for their 5-lipoxygenase (5-LOX) mediated LTB4 formation inhibitory activity using an assay with activated human polymorphonuclear leukocytes. The derivatization reactions included methylation, acetylation, hydrogenation, epoxydation and isomerization. Five of the derivatives are new to science. The most active compound against COX-1 and COX-2 was methylhonokiol with IC50 values of 0.1 mu M, whereas the most active compound against LTB4 formation was (E)-3'-propenyl-5-(2-propenyl)-biphenyl-2,4'-diol with an IC50 value of 1.0 mu M. Structure-activity relationship studies showed that the polarity of the derivatives plays a crucial role in their activity towards COX-1/2 enzyme and 5-LOX mediated LTB4 formation. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Bisphenol Neolignans Inspired by Honokiol as Antiproliferative Agents
  作者：Nunzio Cardullo、Vincenza Barresi、Vera Muccilli、Giorgia Spampinato、Morgana D’Amico、Daniele Filippo Condorelli、Corrado Tringali

  DOI：10.3390/molecules25030733

  日期：——

  Honokiol (2) is a natural bisphenol neolignan showing a variety of biological properties, including antitumor activity. Some studies pointed out 2 as a potential anticancer agent in view of its antiproliferative and pro-apoptotic activity towards tumor cells. As a further contribution to these studies, we report here the synthesis of a small library of bisphenol neolignans inspired by honokiol and the evaluation

  Honokiol (2) 是一种天然双酚新木脂素，具有多种生物学特性，包括抗肿瘤活性。鉴于其对肿瘤细胞的抗增殖和促凋亡活性，一些研究指出 2 作为潜在的抗癌剂。作为对这些研究的进一步贡献，我们在此报告了受和厚朴酚启发的小型双酚新木脂素库的合成及其抗增殖活性的评估。因此，对天然铅进行简单的化学修饰以获得衍生物 3-9；进一步的新木脂素（12a-c、13a-c、14a-c 和 15a）采用 Suzuki-Miyaura 反应合成，从而获得取代模式不同于和厚朴酚的双酚。这些化合物和天然铅对 HCT-116、HT-29、和 PC3 肿瘤细胞系。六个新木脂素对所有细胞系的 GI50 值均低于 2 个。化合物14a、14c和15a是最有效的抗增殖剂，GI50在3.6-19.1 µM范围内，在某些情况下低于抗癌药物5-氟尿嘧啶。对这些新木脂素进行的流式细胞术实验表明，增殖的抑制主要是由于细胞凋亡过程。这