5-allyl pyrogallol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-allyl pyrogallol
• 英文别名: 5-Allylbenzene-1,2,3-triol；5-prop-2-enylbenzene-1,2,3-triol
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: ZYRIJURXMYXWQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  5-allyl pyrogallol 、 碘甲烷 在 silver(l) oxide 作用下， 生成 榄香素
  参考文献：
  名称：

  Piotrowska, Dorota G.; Wróblewski, Andrzej E.; Balzarini, Jan, Acta poloniae pharmaceutica, 2017, vol. 74, # 4, p. 1091 - 1100

  摘要：

  DOI：
• 作为产物：
  描述：

  4-烯丙基-2,6-二甲氧基苯酚 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以68%的产率得到5-allyl pyrogallol
  参考文献：
  名称：

  Structure–Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from <i>Piper betle</i>

  摘要：

  Malaria disease remains a serious worldwide health problem. In South-East Asia, one of the malaria infection "hot-spots," medicinal plants such as Piper betle have traditionally been used for the treatment of malaria, and allylpyrocatechol (1), a constituent of P. betle, has been shown to exhibit anti-malarial activities. In this study, we verified that 1 showed in vivo anti-malarial activity through not only intraperitoneal (i.p.) but also peroral (p.o.) administration. Additionally, some analogs of 1 were synthesized and the structure-activity relationship was analyzed to disclose the crucial sub-structures for the potent activity.

  DOI：

  10.1248/cpb.c20-00294

文献信息

• Structure–Activity Relationships and Docking Studies of Hydroxychavicol and Its Analogs as Xanthine Oxidase Inhibitors
  作者：Keiji Nishiwaki、Kanae Ohigashi、Takahiro Deguchi、Kazuya Murata、Shinya Nakamura、Hideaki Matsuda、Isao Nakanishi

  DOI：10.1248/cpb.c18-00197

  日期：2018.7.1

  16.7 µM, making it more potent than the clinically used allopurinol (IC50=30.7 µM). Herein, a structure-activity relationship analysis of the polar part analogs of HC was conducted and an inhibitor was discovered with a potency 13 times that of HC. Kinetic studies have revealed that HC and its active analog inhibit XO in an uncompetitive manner. The binding structure prediction of these inhibitor molecules

  羟基邻苯二酚（HC），是从Piper betle LINN的叶子中获得的。（Piperaceae）可抑制黄嘌呤氧化酶（XO），IC50值为16.7 µM，使其比临床使用的别嘌呤醇（IC50 = 30.7 µM）更有效。在此，对HC的极性部分类似物进行了构效关系分析，发现了一种抑制剂，其效价是HC的13倍。动力学研究表明，HC及其活性类似物以非竞争性方式抑制XO。这些抑制剂分子与黄嘌呤的XO配合物的结合结构预测表明，这两种化合物（HC及其类似物）都可以同时与黄嘌呤和XO形成氢键。
• [EN] PRODUCTION OF HIGHLY PURE META,META-COUPLED BIS(4-ALKYLPHENOL) DERIVATIVES AND USES THEREOF<br/>[FR] PRODUCTION DE DÉRIVÉS DE BIS(4-ALKYLPHÉNOL) MÉTA,MÉTA-COUPLÉS TRÈS PURS ET LEURS UTILISATIONS
  申请人：UNIV LEUVEN KATH

  公开号：WO2018134427A1

  公开（公告）日：2018-07-26

  In general the present invention concerns a method for production of highly pure m,m'- coupled bis(4-alkylphenol) derivatives from particular lignin-derived 4-alkylphenol derivatives. More specifically this invention relates to a process for the selective purification of m,m'- coupled bis(4-alkylphenol) derivatives by selective crystallization in the presence of residual substrate and isomeric and/or oligomeric by-products/impurities. This new class of bis(4-alkylphenol)s are valuable precursors for renewable thermoplastics, (high temperature) resins/thermosets, bio-derived C15-C19 fuel additives, antioxidants, UV-stabilizers, plasticizers, soluble n-type perylene copolymers and/or positive working photoresists.

  总的来说，本发明涉及一种从特定木质素衍生的4-烷基酚衍生物生产高纯度m，m'-偶联的双(4-烷基酚)衍生物的方法。更具体地说，本发明涉及一种通过在残留底物和同分异构体和/或寡聚体副产物/杂质存在下进行选择性结晶实现对m，m'-偶联的双(4-烷基酚)衍生物的选择性纯化的方法。这种新类别的双(4-烷基酚)是可再生热塑性塑料、(高温)树脂/热固性塑料、生物衍生的C15-C19燃料添加剂、抗氧化剂、紫外线稳定剂、增塑剂、可溶性n-型苝共聚物和/或正向光刻胶的有价值前体。
• [EN] PRODUCTION OF 3-ALKYLPHENOLS AND USES THEREOF<br/>[FR] PRODUCTION DE 3-ALKYLPHÉNOLS ET LEURS UTILISATIONS
  申请人：UNIV LEUVEN KATH

  公开号：WO2016187678A1

  公开（公告）日：2016-12-01

  In general the present invention concerns a method for conversion of particular 4-alkyl-2- hydroxyphenols and 4-alkyl-2-alkoxyphenols into 3-alkylphenols. More specifically, this invention relates to a novel process of selectively forming meta-alkyl phenols of various alkylphenols, such as for instance converting the fraction of 4-alkyl-2-hydroxyphenols and 4- alkyl-2-alkoxyphenols into high yields of 3-alkylphenols.

  一般来说，本发明涉及一种将特定的4-烷基-2-羟基苯酚和4-烷基-2-烷氧基苯酚转化为3-烷基苯酚的方法。更具体地说，本发明涉及一种新颖的选择性形成各种烷基苯酚的间位烷基苯酚的方法，例如将4-烷基-2-羟基苯酚和4-烷基-2-烷氧基苯酚的部分转化为高收率的3-烷基苯酚。
• CHRYSOPHAENTIN ANALOGS THAT INHIBIT FTSZ PROTEIN
  申请人：Bewley Carole A.

  公开号：US20130331460A1

  公开（公告）日：2013-12-12

  Embodiments of antimicrobial chrysophaentin compounds, pharmaceutical compositions including the chrysophaentin compounds, methods for using the chrysophaentin compounds, and methods for synthesizing the chrysophaentin compounds are disclosed. Certain embodiments of the chrysophaentin compounds inhibit FtsZ protein, thereby inhibiting the growth of clinically relevant bacteria, including drug-resistant strains.

  本文揭示了抗微生物药物Chrysophaentin化合物的实施例，包括该化合物的制药组合物，使用该化合物的方法以及合成该化合物的方法。某些实施例的Chrysophaentin化合物抑制FtsZ蛋白，从而抑制临床相关细菌的生长，包括耐药菌株。
• CHRYSOPHAENTIN ANTIMICROBIAL COMPOUNDS THAT INHIBIT FTSZ PROTEIN
  申请人：The United States of America, as represented by The Secretary, Department of Health and Human Services

  公开号：EP2539305A2

  公开（公告）日：2013-01-02