honokiol dimonoacetate | 35347-50-3

• 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: honokiol dimonoacetate
• 英文别名: Honokioldiacetat；2,4'-diacetoxy-5,3'-di(2-propenyl)biphenyl；2,4''-Diacetoxy-5,3''-di-(2-propenyl)-biphenyl；[4-(2-acetyloxy-5-prop-2-enylphenyl)-2-prop-2-enylphenyl] acetate
• CAS: 35347-50-3
• 化学式: C₂₂H₂₂O₄
• 分子量: 350.414
• InChiKey: XNFZWGDLKCJOLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  honokiol dimonoacetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以9.7 mg的产率得到和厚朴酚
  参考文献：
  名称：

  Efficient synthesis of neurotrophic honokiol using Suzuki–Miyaura reactions

  摘要：

  Efficient synthesis of honokiol (1) was accomplished using two kinds of Suzuki-Miyaura reactions. The first Suzuki-Miyaura reaction was employed to couple 2-bromophenol (6) with 4-hydroxyphenylboronic acid (5), giving rise to biphenol 4, and the second coupling was used to introduce allyl groups at 5- and 3'-positions of honokiol. The total synthesis of 1 was completed in 74% yield over five steps from 6, or in 83% yield over four steps from biphenol 4. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.040
• 作为产物：
  描述：

  [1,1-双苯基]-2,4-二醇 在 吡啶 、 二硫化碳 、 四(三苯基膦)钯 、 溴 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 honokiol dimonoacetate
  参考文献：
  名称：

  Efficient synthesis of neurotrophic honokiol using Suzuki–Miyaura reactions

  摘要：

  Efficient synthesis of honokiol (1) was accomplished using two kinds of Suzuki-Miyaura reactions. The first Suzuki-Miyaura reaction was employed to couple 2-bromophenol (6) with 4-hydroxyphenylboronic acid (5), giving rise to biphenol 4, and the second coupling was used to introduce allyl groups at 5- and 3'-positions of honokiol. The total synthesis of 1 was completed in 74% yield over five steps from 6, or in 83% yield over four steps from biphenol 4. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.040

文献信息

• [EN] MITO-HONOKIOL COMPOUNDS AND METHODS OF SYNTHESIS AND USE THEREOF<br/>[FR] COMPOSÉS MITO-HONOKIOL ET LEURS PROCÉDÉS DE SYNTHÈSE ET D'UTILISATION
  申请人：MEDICAL COLLEGE WISCONSIN INC

  公开号：WO2016201188A1

  公开（公告）日：2016-12-15

  The present invention provides mito-honokiol compounds, pharmaceutical compositions thereof, and methods of using the mito-honokiol compounds in the treatment of cancer.

  本发明提供了mito-honokiol化合物、其药物组合物以及使用mito-honokiol化合物治疗癌症的方法。
• Synthesis of magnolol and honokiol derivatives and their effect against hepatocarcinoma cells
  作者：Margherita Maioli、Valentina Basoli、Paola Carta、Davide Fabbri、Maria Antonietta Dettori、Sara Cruciani、Pier Andrea Serra、Giovanna Delogu

  DOI：10.1371/journal.pone.0192178

  日期：——

  The hepatocellular carcinoma is one of the most common malignant tumour with high level of mortality rate due to its rapid progression and high resistance to conventional chemotherapies. Thus, the search for novel therapeutic leads is of global interest. Herein, a small set of derivatives of magnolol 1 and honokiol 2, the main components of Magnolia grandiflora and Magnolia obovata, were evaluated in in vitro assay using tumoral hepatocytes. The pro-drug approach was applied as versatile strategy to the improve bioactivity of the compounds by careful transformation of the hydroxyl groups of magnolol 1 and honokiol 2 in suitable ester derivatives. Compounds 10 and 11 resulted to be more potent than the parental honokiol 2 at concentration down to 1 μM with complete viability of treated fibroblast cells up to concentrations of 80 μM. The combination of a butyrate ester and a bare phenol-OH group in the honokiol structure seemed to play a significant role in the antiproliferative activity identifying an interesting pharmacological clue against hepatocellular carcinoma.

  肝细胞癌是最常见的恶性肿瘤之一，由于其进展迅速和对传统化疗的耐药性强，死亡率很高。因此，寻找新的治疗线索受到全球关注。在此，研究人员利用肿瘤肝细胞，在体外试验中评估了木兰醇 1 和厚朴酚 2（厚朴和白玉兰的主要成分）的一小部分衍生物。通过将厚朴酚 1 和厚朴酚 2 的羟基仔细转化为合适的酯类衍生物，将原药方法作为提高化合物生物活性的多功能策略加以应用。结果发现，化合物 10 和 11 在浓度低至 1 μM 时比亲代的 honokiol 2 更有效，在浓度高达 80 μM 时，经处理的成纤维细胞可完全存活。在 honokiol 的结构中，丁酸酯和裸露的苯酚-OH 基团的组合似乎在抗增殖活性中发挥了重要作用，为抗击肝细胞癌提供了一条有趣的药理学线索。
• 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
• Synthesis and microbiological evaluation of honokiol derivatives as new antimicrobial agents
  作者：Young-Soo Kim、Ji-Young Lee、Junho Park、Wangtaek Hwang、Jongsung Lee、Deokhoon Park

  DOI：10.1007/s12272-010-2225-7

  日期：2010.1

  Honokiol, a major phenolic constituent of Magnolia sp., has various pharmacological activities. To improve the solubility and antibacterial activity of honokiol against E. coli and P. aeruginosa, new honokiol-derivatives (honokiol-acetate, honokiol-succinic acid, honokiol-glycerol, honokiol-glycine, honokiol-glucose and honokiol-mannose) were synthesized and their solubility and antimicrobial activities were investigated. Among the tested compounds, honokiol-glycine showed improved water solubility and antibacterial activities against E. coli and P. aeruginosa when compared to honokiol.

  厚朴酚是厚朴属植物的一种主要酚类成分，具有多种药理活性。为了提高厚朴酚的溶解性和对大肠杆菌和绿脓杆菌的抗菌活性，研究人员合成了新的厚朴酚衍生物（厚朴酚-乙酸酯、厚朴酚-琥珀酸、厚朴酚-甘油、厚朴酚-甘氨酸、厚朴酚-葡萄糖和厚朴酚-甘露糖），并对它们的溶解性和抗菌活性进行了研究。在测试的化合物中，与 honokiol 相比，honokiol-甘氨酸的水溶性更好，对大肠杆菌和绿脓杆菌的抗菌活性也更强。
• Biomimetic Total Synthesis of Bimagnolignan: A Natural Anti-Breast Cancer Agent
  作者：Yu-Hong Liu、Yu-Ting Liao、Xiao-Dan Shao、Zhu-Ya Yang、Dashan Li、Lu Liu、Li-Dong Shao

  DOI：10.1021/acs.orglett.4c00378

  日期：2024.3.29

  short scalable biomimetic route to bioactive natural product bimagnolignan (1) was accomplished. Compound 1 was successfully prepared through a three-step metal-free synthesis from honokiol (2). Alternatively, 1 was also synthesized by biomimetic transformations that mimic tyrosinase in four steps. The key reactions feature a regioselective acetylation, a highly efficient C(sp2)–H oxidation, a cascade

  完成了一种生产生物活性天然产物双木脂素（ 1 ）的短的可扩展仿生路线。通过三步无金属合成法，由和厚朴酚 ( 2 ) 成功制备出化合物1 。或者， 1也可以通过模拟酪氨酸酶的仿生转化分四个步骤合成。关键反应包括区域选择性乙酰化、高效C(sp 2 )–H氧化、级联有氧氧化环化/偶联以及Cu催化的直接氧化偶联。此外，基于细胞的检测证实1是治疗 HER2 阳性乳腺癌的一种有前景的天然先导药物。