Tetrahydrohonokiol | 35406-31-6

• 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: Tetrahydrohonokiol
• 英文别名: 3',5-dipropyl-(1,1'-biphenyl)-2,4'-diol；[1,1'-Biphenyl]-2,4'-diol, 3',5-dipropyl-；2-(4-hydroxy-3-propylphenyl)-4-propylphenol
• CAS: 35406-31-6
• 化学式: C₁₈H₂₂O₂
• 分子量: 270.371
• InChiKey: PJBHWFHBOPMXAM-UHFFFAOYSA-N

物化性质

• 沸点：
  399.6±37.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Tetrahydrohonokiol 在 硝酸 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 1.34h， 生成 4'-methoxy-3-nitro-3',5-dipropyl-biphenyl-2-ol
  参考文献：
  名称：

  Synthesis of Tetrahydrohonokiol Derivates and Their Evaluation for Cytotoxic Activity against CCRF-CEM Leukemia, U251 Glioblastoma and HCT-116 Colon Cancer Cells

  摘要：

  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。

  DOI：

  10.3390/molecules19011223
• 作为产物：
  描述：

  5-溴水杨酸 在 Wilkinson's catalyst 吡啶 、 盐酸 、 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 硫酸 、 氢氟酸 、 氢气 、 potassium acetate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 Tetrahydrohonokiol
  参考文献：
  名称：

  Efficient synthesis and structure–activity relationship of honokiol, a neurotrophic biphenyl-type neolignan

  摘要：

  Honokiol, a biphenyl-type neolignan, which shows the remarkable neurotrophic effect in primary cultured rat cortical neurons, has been effectively synthesized in 21% yield over 14 steps starting from 5-bromosalicylic acid and p-hydroxybenzoic acid by utilizing Pd-catalyzed Suzuki-Miyaura coupling reaction as a key step. Additionally, the structure-activity relationship between neurite outgrowth-promoting activity and its O-methylated and/or its hydrogenated analogues was examined in the primary cultures of fetal rat cortical neurons, suggesting that 5-allyl and T-hydroxyl groups are essential for affecting the neurotrophic activity of honokiol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.067

文献信息

• METHOD OF PRODUCING BIPHENOLIC COMPOUND, NOVEL BIPHENYL COMPOUND AND SYNTHESIS METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR TREATING PARKINSON'S DISEASE
  申请人：Chan Ming-Huan

  公开号：US20130303788A1

  公开（公告）日：2013-11-14

  A method of producing honokiol and analogues thereof, and novel intermediates prepared by virtue thereof are disclosed herein. A pharmaceutical composition for treating Parkinson's disease, which contains honokiol and/or the analogues thereof, is also disclosed herein.

  本发明公开了一种生产厚朴酚及其类似物的方法，以及由此制备的新颖中间体。还公开了一种用于治疗帕金森病的药物组合物，该组合物包含厚朴酚和/或其类似物。
• 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
• Anti-proliferative activity and structure-activity relationship of honokiol derivatives
  作者：Ding Lin、Zhongzhong Yan、Aiyu Chen、Jiao Ye、Aixi Hu、Juan Liu、Junmei Peng、Xiaoyun Wu

  DOI：10.1016/j.bmc.2019.06.042

  日期：2019.8

  product with anti-tumor activity, honokiol has been widely researched and structural modified. Lots of honokiol derivatives have been found to possess good anti-proliferative activity and showed great potential in cancer therapy, but the SAR (structure-activity relationship) was still confused. Here in, the SAR were comprehensively researched by summary of reported derivatives and synthesis of novel derivatives

  作为已知的具有抗肿瘤活性的天然产物，厚朴酚已被广泛研究和结构改性。已经发现许多厚朴酚衍生物具有良好的抗增殖活性，并在癌症治疗中显示出巨大的潜力，但是SAR（结构-活性关系）仍然令人困惑。在此，通过总结已报道的衍生物和合成新的衍生物，对合成孔径雷达进行了全面的研究。在新的衍生物中，有希望的化合物A6和A10对K562细胞系表现出有效的和选择性的抗增殖活性，IC50值分别为5.04和7.08μM。通过CoMFA和理论计算，围绕厚朴酚和79种衍生物讨论了SAR，为厚朴酚衍生物的进一步结构优化提供了有益的建议。
• An expedient synthesis of honokiol and its analogues as potential neuropreventive agents
  作者：Subhankar Tripathi、Ming-Huan Chan、Chinpiao Chen

  DOI：10.1016/j.bmcl.2011.11.030

  日期：2012.1

  An efficient synthesis of honokiol with Suzuki-Miyaura cross coupling obtained an overall yield of 45%. The proposed approach successfully synthesized several structurally similar alkyl, alkenyl and alkynyl analogues, seven of which showed potential neuropreventive activity against MPP+-induced and CHP/TBHP oxidative stress induced neuroblastoma cell death. (C) 2011 Elsevier Ltd. All rights reserved.
• Cytotoxic neolignans: an SAR study
  作者：Zwe-Ling Kong、Shin-Cheng Tzeng、Yeuk-Chuen Liu

  DOI：10.1016/j.bmcl.2004.10.011

  日期：2005.1

  The neolignans, magnolol 1 and honokiol 2 have been reported to inhibit the growth of several tumor cell lines in vitro and in vivo. The chemical structure of magnolol and honokiol consists of biphenyl skeleton with phenolic and allylic functionalities. Analogs of 1 and 2 containing different substitution have been studies for their effect on the growth of Hep-G2 and their structure-activity relationships were reported in this work. (C) 2004 Elsevier Ltd. All rights reserved.