5-(6-bromo-2-methylhexan-2-yl)resorcinol | 215649-02-8

• 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: 5-(6-bromo-2-methylhexan-2-yl)resorcinol
• 英文别名: 1,3-Benzenediol, 5-(5-bromo-1,1-dimethylpentyl)-；5-(6-bromo-2-methylhexan-2-yl)benzene-1,3-diol
• CAS: 215649-02-8
• 化学式: C₁₃H₁₉BrO₂
• 分子量: 287.197
• InChiKey: VIOWIWPAGUWFGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  5-(6-bromo-2-methylhexan-2-yl)resorcinol 在 对甲苯磺酸 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 3.0h， 生成 O 581
  参考文献：
  名称：

  Potent Cyano and Carboxamido Side-Chain Analogues of 1‘,1‘-Dimethyl-Δ⁸-Tetrahydrocannabinol

  摘要：

  The synthesis and pharmacological profile of several cyano (1a-e) and carboxamido (2a-h) side-chain-substituted analogues of 1',1'-dimethyl-Delta(8)-THC are described. Commercially available cyano compound 3 was transformed to the resorcinol 6 in a three-step sequence. Condensation of 6 with p-menth-2-ene-1,8-diol formed the THC 7a which, with sodium cyanide/ DMSO, gave Ib. Protection of the phenol in 7a as the MOM derivative provided the common intermediate 8 for the synthesis of 1a,c,e. Compound 1d was also synthesized from 7a via the aldehyde 9a. Base hydrolysis of 1b gave the acid 10 which, via its acid chloride and subsequent treatment with the appropriate amine, formed the target compounds 2a-h. The pharmacological profile indicated that the cyano analogues 1a-e had very high CB1 binding affinity (0.36-13 nM) and high in vivo potency as agonists. Two analogues (1a,b) had extremely high potency in the mouse tetrad tests. The dimethylcarboxamido analogue 2a showed a similar profile to 1a,b. The high potency was also retained in analogue 2c. In contrast the sulfonamide analogue 2d was unique as it had greater affinity than Delta(9)-THC, yet it was practically devoid of agonist effects. This study suggests that the incorporation of a cyano or an amide substituent in the side chain of Delta(8)-THC-DMH can enhance potency and can also lead to compounds with a unique profile which have high binding affinity and are practically devoid of agonist effects.

  DOI：

  10.1021/jm9803875
• 作为产物：
  描述：

  3,5-二甲氧基苯腈 在 盐酸 、 三溴化硼 、 四氯化钛 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 7.17h， 生成 5-(6-bromo-2-methylhexan-2-yl)resorcinol
  参考文献：
  名称：

  Potent Cyano and Carboxamido Side-Chain Analogues of 1‘,1‘-Dimethyl-Δ⁸-Tetrahydrocannabinol

  摘要：

  The synthesis and pharmacological profile of several cyano (1a-e) and carboxamido (2a-h) side-chain-substituted analogues of 1',1'-dimethyl-Delta(8)-THC are described. Commercially available cyano compound 3 was transformed to the resorcinol 6 in a three-step sequence. Condensation of 6 with p-menth-2-ene-1,8-diol formed the THC 7a which, with sodium cyanide/ DMSO, gave Ib. Protection of the phenol in 7a as the MOM derivative provided the common intermediate 8 for the synthesis of 1a,c,e. Compound 1d was also synthesized from 7a via the aldehyde 9a. Base hydrolysis of 1b gave the acid 10 which, via its acid chloride and subsequent treatment with the appropriate amine, formed the target compounds 2a-h. The pharmacological profile indicated that the cyano analogues 1a-e had very high CB1 binding affinity (0.36-13 nM) and high in vivo potency as agonists. Two analogues (1a,b) had extremely high potency in the mouse tetrad tests. The dimethylcarboxamido analogue 2a showed a similar profile to 1a,b. The high potency was also retained in analogue 2c. In contrast the sulfonamide analogue 2d was unique as it had greater affinity than Delta(9)-THC, yet it was practically devoid of agonist effects. This study suggests that the incorporation of a cyano or an amide substituent in the side chain of Delta(8)-THC-DMH can enhance potency and can also lead to compounds with a unique profile which have high binding affinity and are practically devoid of agonist effects.

  DOI：

  10.1021/jm9803875

文献信息

• [EN] 2-CYCLOALKYL RESORCINOL CANNABINERGIC LIGANDS<br/>[FR] LIGANDS CANNABINERGIQUES DE 2-CYCLOALKYL RÉSORCINOL
  申请人：UNIV NORTHEASTERN

  公开号：WO2014062965A1

  公开（公告）日：2014-04-24

  The present invention relates to novel 2-cycloalkyl resorcinol compounds; to pharmaceutical compositions comprising the compounds; and to methods of preparing the compounds and uses thereof. The disclosed compounds can bind to and modulate the cannabinoid receptors and thus, they are specific ligands for these receptors. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本发明涉及新型2-环烷基间苯二酚化合物；包括这些化合物的药物组合物；以及制备这些化合物和它们的用途的方法。所披露的化合物可以结合并调节大麻素受体，因此它们是这些受体的特异性配体。当将这些发明的化合物以治疗有效剂量的方式给予个体或动物时，会在个体或动物体内产生足够高水平的该化合物，从而引起生理反应。这种生理反应可能有助于治疗多种生理状况。
• [EN] WATER-SOLUBLE CANNABINOIDS<br/>[FR] CANNABINOIDES SOLUBLES DANS L'EAU
  申请人：UNIV VIRGINIA COMMONWEALTH

  公开号：WO2006012176A1

  公开（公告）日：2006-02-02

  Water-soluble cannabinoid compounds that are agonists of CB1 and CB2 cannabinoid receptors are provided. The compounds are made water-soluble by derivatization of the alkyl side chain and/or the phenolic hydroxyl group of tetrahydrocannabinol. The water-soluble cannabinoids are useful for the treatment of appetite loss, pain, multiple sclerosis, nausea and vomiting, and epilepsy.

  提供了一种可以溶于水的作用于CB1和CB2大麻素受体的大麻素类化合物。通过对四氢大麻酚的烷基侧链和/或酚羟基进行衍生化，使这些化合物可以溶于水。这些水溶性大麻素化合物可用于治疗食欲不振、疼痛、多发性硬化症、恶心和呕吐以及癫痫等疾病。
• ONE-STEP FLOW-MEDIATED SYNTHESIS OF CANNABIDIOL (CBD) AND DERIVATIVES
  申请人：TRUSTEES OF BOSTON UNIVERSITY

  公开号：US20200325091A1

  公开（公告）日：2020-10-15

  Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.

  本文描述了用于制备大麻素（如大麻二酚CBD）及其衍生物的装置和工艺。所描述的装置和工艺可用于一步法、流程介导的合成大麻二酚及其衍生物，相对于批处理过程，具有更高的总产量、材料通过量和产品纯度。
• 2-CYCLOALKYL RESORCINOL CANNABINERGIC LIGANDS
  申请人：NORTHEASTERN UNIVERSITY

  公开号：US20150274623A1

  公开（公告）日：2015-10-01

  The present invention relates to novel 2-cycloalkyl resorcinol compounds; to pharmaceutical compositions comprising the compounds; and to methods of preparing the compounds and uses thereof. The disclosed compounds can bind to and modulate the cannabinoid receptors and thus, they are specific ligands for these receptors. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本发明涉及一种新型的2-环烷基邻苯二酚化合物；涉及含有该化合物的药物组合物；以及制备该化合物和使用该化合物的方法。所披露的化合物能够结合和调节大麻素受体，因此它们是这些受体的特异性配体。当以治疗有效量的方式给予这些发明化合物给个体或动物时，会在个体或动物中产生足够高的该化合物水平以引起生理反应。这种生理反应可能有助于治疗许多生理状况。
• CANNABINERGIC NITRATE ESTERS AND RELATED ANALOGS
  申请人：Northeastern University

  公开号：US20160002195A1

  公开（公告）日：2016-01-07

  The present technology relates to novel cannabinergic nitrate esters and related analogs, process of preparation, pharmaceutical compositions and their methods of use as medicaments, pharmacological tools and/or biomarkers. The novel cannabinergic nitrate ester compounds provide medicaments useful in treating a variety of diseases and medical disorders.

  本技术涉及新型大麻素硝酸酯及其类似物、制备方法、制药组合物及其作为药物、药理工具和/或生物标志物的使用方法。这些新型大麻素硝酸酯化合物提供了治疗各种疾病和医学障碍的有用药物。