3-allylresorcinol | 142039-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-allylresorcinol
• 英文别名: 5-Allylbenzene-1,3-diol；5-prop-2-enylbenzene-1,3-diol
• CAS: 142039-78-9
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: ANHJRLYMAOROEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-allylresorcinol 在 亚磷酸三苯酯 、 氢气 作用下， 以 氯仿 为溶剂， 生成 5-丙基-1,3-苯二酚
  参考文献：
  名称：

  Substrate Selective Catalysis by Rhodium Metallohosts

  摘要：

  A novel supramolecular catalyst functioning according to the principles of enzymatic catalysis is described. It consists of a basket-shaped molecule to which a catalytically active Rh(I) complex is attached. The catalyst selectively hydrogenates and isomerizes allyl-substituted dihydroxyarene substrates that are bound in its cavity. The reactivity of this supramolecular catalyst and its affinity for several substrates is compared with that of the corresponding catalyst without a binding site. Features known from enzymatic catalysis, e.g. Michaelis-Menten kinetics and rate enhancement by cooperative binding, are described and discussed.

  DOI：

  10.1021/ja00153a012
• 作为产物：
  描述：

  1-烯丙基-3,5-二甲氧基苯 在 碘 、 氢化铝 作用下， 以 二硫化碳 为溶剂， 以81%的产率得到3-allylresorcinol
  参考文献：
  名称：

  通过交叉偶联反应合成 5-取代的间苯二酚衍生物

  摘要：

  Suzuki 和 Stille 交叉偶联反应用于合成 5-取代的 1,3-二甲氧基苯和 5-取代的间苯二酚衍生物。取代的间苯二酚衍生物仅通过三个步骤从廉价的试剂中获得。1,3-二甲氧基苯甲酸和1-氯-3,5-二甲氧基苯转化为1-碘-、1-溴-、1-三甲基锡-3,5-二甲氧基苯和3,5-二甲氧基苯基硼酸。5-烯丙基-1,3-二甲氧基苯和3,5-二甲氧基联苯衍生物是在温和条件下通过交叉偶联反应获得的。HI、BBr3 和AlI3 用于将这些二甲氧基苯去甲基化成它们的间苯二酚衍生物。

  DOI：

  10.1002/(sici)1099-0690(199802)1998:2<359::aid-ejoc359>3.0.co;2-n

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。
• NOVEL ANALGESIC AND IMMUNOMODULATORY CANNABINOIDS
  申请人：——

  公开号：US20010009965A1

  公开（公告）日：2001-07-26

  Disclosed are novel compounds represented by the following structural formula: R—X—Y; and physiologically acceptable salts thereof. R is a tricyclic core of a cannabinoid or substituted cannabinoid. X is a covalent bond, —CH2— or —CHR 1 —, wherein R 1 a C1 to C3 substituted or unsubstituted alkyl group. Y is a heterocyclic ring, a substituted heterocyclic ring, a carbocyclic ring, a substituted carbocyclic ring, a fused bicyclic ring system, a substituted fused bicyclic ring system, a bridged bicyclic ring system, a substituted bridged bicyclic ring system, a bridged tricyclic ring system or a substituted bridged tricyclic ring system. Also disclosed is a method of stimulating a CB1 and/or CB2 receptor in a subject. The method comprises administering to the subject a therapeutically effective amount of R—X—Y.

  本发明涉及一种新型化合物，其结构式如下：R—X—Y；以及其生理上可接受的盐。其中，R是大麻素或取代大麻素的三环核心；X是共价键，—CH2—或—CHR1—，其中R1是C1到C3的取代或未取代烷基；Y是杂环环、取代的杂环环、碳环、取代的碳环、融合的双环系统、取代的融合的双环系统、桥接的双环系统、取代的桥接的双环系统、桥接的三环环系统或取代的桥接的三环环系统。本发明还涉及一种刺激受体CB1和/或CB2的方法。该方法包括向受体中注射R—X—Y的治疗有效量。
• Topical formulations of resorcinols and cannibinoids and methods of use
  申请人：Immugen Pharmaceuticals, Inc.

  公开号：US20030232101A1

  公开（公告）日：2003-12-18

  In one aspect, the invention provides a method for preventing the transmission of HIV from one individual to another. In accordance with the method, a pharmacologically-acceptable composition including at least one resorcinol derivative compound and/or cannabinoid (e.g., cannabinol derivatives, &Dgr;8-THC derivatives, cannabichromene derivatives, cannabidiol derivatives, cannabigerol derivatives) (including combinations thereof) is administered topically to a first individual harboring HIV, or to a second individual at risk of infection with HIV, proximate in time with contact between the first individual and the second individual. The invention also provides topical formulations of at least one resorcinol and/or cannabinoid and water insoluble polymers as hydrogels.

  本发明提供了一种预防HIV从一个个体传播到另一个个体的方法。根据该方法，将至少包括一种间苯二酚衍生物化合物和/或大麻素（例如，大麻酚衍生物，Δ8-THC衍生物，大麻烯衍生物，大麻二酚衍生物，大麻醇衍生物）（包括其组合）的药理学可接受的组合物局部给第一具有HIV的个体，或在第一具有HIV的个体和第二个个体之间的接触时间接近时局部给第二个有HIV感染风险的个体。本发明还提供了至少包括一种间苯二酚和/或大麻素以及水不溶性聚合物作为水凝胶的局部制剂。
• [EN] PROCESS FOR THE PREPARATION OF 3-SUBSTITUTED CANNABINOID COMPOUNDS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS CANNABINOÏDES 3-SUBSTITUÉS
  申请人：E-THERAPEUTICS PLC

  公开号：WO2017093749A1

  公开（公告）日：2017-06-08

  There is described a method of preparing a compound of formula I, and optical isomers thereof: in which R1 is hydrogen or a protecting group; said method comprising oxidising verbenone and optical isomers thereof.

  本文描述了一种制备化合物I及其光学异构体的方法：其中R1为氢或保护基；该方法包括氧化薄荷酮和其光学异构体。
• Novel analgesic and immunomodulatory cannabinoids
  申请人：Makriyannis Alexandros

  公开号：US20050239874A1

  公开（公告）日：2005-10-27

  Disclosed are novel compounds represented by the following structural formula: R—X—Y; and physiologically acceptable salts thereof. R is a tricyclic core of a cannabinoid or substituted cannabinoid. X is a covalent bond, —CH 2 — or —CHR 1 —, wherein R 1 a C1 to C3 substituted or unsubstituted alkyl group. Y is a heterocyclic ring, a substituted heterocyclic ring, a carbocyclic ring, a substituted carbocyclic ring, a fused bicyclic ring system, a substituted fused bicyclic ring system, a bridged bicyclic ring system, a substituted bridged bicyclic ring system, a bridged tricyclic ring system or a substituted bridged tricyclic ring system. Also disclosed is a method of stimulating a CB1 and/or CB2 receptor in a subject. The method comprises administering to the subject a therapeutically effective amount of R—X—Y.

  本发明涉及一种新型化合物，其结构式为：R—X—Y；以及其生理上可接受的盐。其中，R是大麻素或取代大麻素的三环核心；X是共价键，-CH2-或-CHR1-，其中R1是一个取代或未取代的C1到C3烷基；Y是一个杂环环、取代的杂环环、碳环、取代的碳环、融合的双环环系统、取代的融合的双环环系统、桥接的双环环系统、取代的桥接的双环环系统、桥接的三环环系统或取代的桥接的三环环系统。本发明还涉及一种刺激受体CB1和/或CB2的方法。该方法包括向受体中注射治疗有效量的R—X—Y化合物。

表征谱图