3-methylobovatol

• 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: 3-methylobovatol
• 英文别名: 2-Methoxy-4-prop-2-enyl-6-(4-prop-2-enylphenoxy)phenol
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: KCPHPAFKVWQDHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methylobovatol 生成 Acetic acid 4-allyl-2-(4-allyl-phenoxy)-6-methoxy-phenyl ester
  参考文献：
  名称：

  KIJJOA, ANAKE;PINTO, MADALENA M. M.;TANTISEWIE, BUMRUNG;HERZ, WERNER, PHYTOCHEMISTRY, 28,(1989) N, C. 1284-1286

  摘要：

  DOI：
• 作为产物：
  描述：

  丁香酚 在 正丁基锂 、 四磷十氧化物 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 131.75h， 生成 3-methylobovatol
  参考文献：
  名称：

  铜（I）–USY作为Ullmann型O-，N-，S-和C-丙烯酸化反应的无配体和可回收催化剂：范围和在全合成中的应用

  摘要：

  掺杂铜（I）的沸石Cu I- USY被证明是用于各种Ullmann型偶联反应的通用，高效且可回收的催化剂。这种催化材料易于制备且价格便宜，可在无配体的条件下实现多种O-，N-，S-和C-亲核试剂的芳基化和杂芳基化，同时具有大的官能团相容性。这种催化剂促进C-O键形成的功能在3-甲基obovatol（一种具有生物学相关性的天然存在的二芳基醚）的全合成中得到了进一步证明。从机理的角度出发，已经提出了两种竞争途径，这取决于亲核试剂的性质并与所获得的结果一致。

  DOI：

  10.1021/acs.joc.8b00620

文献信息

• A biphenyl type neolignan and a biphenyl ether from Magnolia henryi
  作者：Anake Kijjoa、Madalena M.M. Pinto、Bumrung Tantisewie、Werner Herz

  DOI：10.1016/0031-9422(89)80237-7

  日期：1989.1

  Abstract A new biphenyl type neolignan 5,5′-diallyl-2,2′-dihydroxy-3-methoxybiphenyl and a new related ether 4′,5-diallyl-2-hydroxy-3-methoxybiphenyl ether were isolated from the bark of Magnolia henryi in addition to magnolol (5,5′-diallyl-2,2′-dihydroxybiphenyl).

  摘要 从厚朴的树皮中分离得到一种新的联苯型新木脂素5,5'-二烯丙基-2,2'-二羟基-3-甲氧基联苯和一种新的相关醚4',5-二烯丙基-2-羟基-3-甲氧基联苯醚。除了 magnolol（5,5'-二烯丙基-2,2'-二羟基联苯）之外，还有 henryi。
• Natural preservatives and antimicrobial agents, including compositions thereof
  申请人：Unigen, Inc.

  公开号：US10780173B2

  公开（公告）日：2020-09-22

  Compositions are disclosed herein that comprise a mixture of at least one Albizia extract and a Magnolia extract. In some embodiments, the composition comprises a mixture of at least one Albizia extract enriched for one or more macrocyclic alkaloids and at least one Magnolia extract enrich for one or more lignans.

  本文公开的组合物包括至少一种白花蛇舌草提取物和一种厚朴提取物的混合物。在某些实施方案中，组合物包括至少一种富含一种或多种大环生物碱的白花蛇舌草提取物和至少一种富含一种或多种木脂素的厚朴提取物的混合物。
• Synthesis of obovatol and related neolignan analogues as α-glucosidase and α-amylase inhibitors
  作者：Claudia Sciacca、Nunzio Cardullo、Luana Pulvirenti、Gabriele Travagliante、Alessandro D'Urso、Roberta D'Agata、Emanuela Peri、Patrizia Cancemi、Anaëlle Cornu、Denis Deffieux、Laurent Pouységu、Stéphane Quideau、Vera Muccilli

  DOI：10.1016/j.bioorg.2024.107392

  日期：2024.6

  bioinspired analogues have been studied as α-Glu and α-Amy inhibitors. However, no studies have been devoted to the evaluation of α-Glu and α-Amy inhibition by the neolignan obovatol (). In this work, we report the synthesis of and a library of new analogues. The synthesis of these compounds was achieved by implementing methodologies based on: phenol allylation, Claisen/Cope rearrangements, methylation

  糖尿病是一种以高血糖为特征的代谢性疾病，可通过抑制负责碳水化合物水解的α-葡萄糖苷酶（α-Glu）和α-淀粉酶（α-Amy）来抵消。近几十年来，许多天然化合物及其仿生类似物已被研究作为 α-Glu 和 α-Amy 抑制剂。然而，还没有研究专门评估新木脂素 obovatol 对 α-Glu 和 α-Amy 的抑制作用 ()。在这项工作中，我们报告了新类似物的合成和新类似物的库。这些化合物的合成是通过实施基于苯酚烯丙基化、克莱森/科普重排、甲基化、乌尔曼偶联、去甲基化、苯酚氧化和迈克尔型加成的方法来实现的。评估了 Obovatol () 和十种类似物对 α-Glu 和 α-Amy 的抑制活性。我们的研究强调，天然存在的四种新木脂素类似物（、、和）是比降血糖药物阿卡波糖（α-Amy：34.6 µM；α-Glu：248.3 µM）更有效的抑制剂，对 α 的 IC 值为 6.2–23.6 µM -Amy
• Synthesis and Structure–Activity Relationship of Dehydrodieugenol B Neolignans against <i>Trypanosoma cruzi</i>
  作者：Claire E. Sear、Pauline Pieper、Maiara Amaral、Maiara M. Romanelli、Thais A. Costa-Silva、Marius M. Haugland、Joseph A. Tate、João H. G. Lago、Andre G. Tempone、Edward A. Anderson

  DOI：10.1021/acsinfecdis.0c00523

  日期：2020.11.13

  Trypanosoma cruzi is the etiologic agent of Chagas disease, which affects over seven million people, especially in developing countries. Undesirable side effects are frequently associated with current therapies, which are typically ineffective in the treatment of all stages of the disease. Here, we report the first synthesis of the neolignan dehydrodieugenol B, a natural product recently shown to exhibit activity against T. cruzi. Using this strategy, a series of synthetic analogues were prepared to explore structure-activity relationships. The in vitro antiparasitic activities of these analogues revealed a wide tolerance of modifications and substituent deletions, with maintained or improved bioactivities against the amastigote forms of the parasite (50% inhibitory concentration (IC₅₀) of 4-63 μM) and no mammalian toxicity (50% cytotoxic concentration (CC₅₀) of >200 μM). Five of these analogues meet the Drugs for Neglected Disease Initiative (DNDi) "hit criteria" for Chagas disease. This work has enabled the identification of key structural features of the natural product and sites where scaffold modification is tolerated.
• Synthesis of 3-Methylobovatol
  作者：David Barker、Lisa Pilkington

  DOI：10.1055/s-0035-1560262

  日期：——

  Biphenyl lignans are rare compounds that exhibit a broad range of biological activities. The first total synthesis of natural biphenyl ether lignan, 3-methylobovatol, has been achieved in four steps. This synthesis allows for modification of the C-2 phenol and in doing so, will facilitate various structure-activity relationship studies into these bioactive compounds.