5-(7-bromo-2-methylhept-2-yl)resorcinol | 941583-93-3

• 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: 5-(7-bromo-2-methylhept-2-yl)resorcinol
• 英文别名: 5-(7-bromo-2-methylheptan-2-yl)benzene-1,3-diol；5-(7-Bromo-2-methylheptan-2-yl)benzene-1,3-diol
• CAS: 941583-93-3
• 化学式: C₁₄H₂₁BrO₂
• 分子量: 301.224
• InChiKey: TZGKYEYVCAUDPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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-(7-bromo-2-methylhept-2-yl)resorcinol 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 C₃₁H₄₇BrO₄
  参考文献：
  名称：

  选择性光亲和探针能够评估人体细胞中大麻素 CB2 受体的表达和配体参与

  摘要：

  非常需要报告 G 蛋白偶联受体 (GPCR) 表达水平和小分子受体占有率的化学工具和方法。我们报告了 LEI121 作为光反应探针的发展，用于研究 2 型大麻素受体 (CB2R)，这是一种治疗组织损伤和炎症疾病的有前途的 GPCR。LEI121 是第一个 CB2R 选择性双功能探针，可在光活化时共价捕获 CB2R。合并的炔作为引入报告基团的连接手柄。LEI121 能够使用流式细胞术对 HL-60 以及原代人类免疫细胞中内源性表达的 CB2R 进行目标参与研究和可视化。

  DOI：

  10.1021/jacs.7b11281
• 作为产物：
  描述：

  2-(3,5-dimethoxyphenyl)-2-methylpropanal 在 palladium on activated charcoal 、 氢气 、 三溴化硼 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.33h， 生成 5-(7-bromo-2-methylhept-2-yl)resorcinol
  参考文献：
  名称：

  Activation and Signaling Mechanism Revealed by Cannabinoid Receptor-Gi Complex Structures

  摘要：

  Human endocannabinoid systems modulate multiple physiological processes mainly through the activation of cannabinoid receptors CB1 and CB2. Their high sequence similarity, low agonist selectivity, and lack of activation and G protein-coupling knowledge have hindered the development of therapeutic applications. Importantly, missing structural information has significantly held back the development of promising CB2-selective agonist drugs for treating inflammatory and neuropathic pain without the psychoactivity of CB1. Here, we report the cryoelectron microscopy structures of synthetic cannabinoid-bound CB2 and CB1 in complex with G(i), as well as agonist-bound CB2 crystal structure. Of important scientific and therapeutic benefit, our results reveal a diverse activation and signaling mechanism, the structural basis of CB2-selective agonists design, and the unexpected interaction of cholesterol with CB1, suggestive of its endogenous allosteric modulating role.

  DOI：

  10.1016/j.cell.2020.01.008

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。
• 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。
• US9517989B2
  申请人：——

  公开号：US9517989B2

  公开（公告）日：2016-12-13
• Selective Photoaffinity Probe That Enables Assessment of Cannabinoid CB₂ Receptor Expression and Ligand Engagement in Human Cells
  作者：Marjolein Soethoudt、Sara C. Stolze、Matthias V. Westphal、Luuk van Stralen、Andrea Martella、Eva J. van Rooden、Wolfgang Guba、Zoltan V. Varga、Hui Deng、Sander I. van Kasteren、Uwe Grether、Adriaan P. IJzerman、Pal Pacher、Erick M. Carreira、Herman S. Overkleeft、Andreea Ioan-Facsinay、Laura H. Heitman、Mario van der Stelt

  DOI：10.1021/jacs.7b11281

  日期：2018.5.16

  Chemical tools and methods that report on G protein-coupled receptor (GPCR) expression levels and receptor occupancy by small molecules are highly desirable. We report the development of LEI121 as a photoreactive probe to study the type 2 cannabinoid receptor (CB2R), a promising GPCR to treat tissue injury and inflammatory diseases. LEI121 is the first CB2R-selective bifunctional probe that covalently

  非常需要报告 G 蛋白偶联受体 (GPCR) 表达水平和小分子受体占有率的化学工具和方法。我们报告了 LEI121 作为光反应探针的发展，用于研究 2 型大麻素受体 (CB2R)，这是一种治疗组织损伤和炎症疾病的有前途的 GPCR。LEI121 是第一个 CB2R 选择性双功能探针，可在光活化时共价捕获 CB2R。合并的炔作为引入报告基团的连接手柄。LEI121 能够使用流式细胞术对 HL-60 以及原代人类免疫细胞中内源性表达的 CB2R 进行目标参与研究和可视化。
• Activation and Signaling Mechanism Revealed by Cannabinoid Receptor-Gi Complex Structures
  作者：Tian Hua、Xiaoting Li、Lijie Wu、Christos Iliopoulos-Tsoutsouvas、Yuxia Wang、Meng Wu、Ling Shen、Christina A. Brust、Spyros P. Nikas、Feng Song、Xiyong Song、Shuguang Yuan、Qianqian Sun、Yiran Wu、Shan Jiang、Travis W. Grim、Othman Benchama、Edward L. Stahl、Nikolai Zvonok、Suwen Zhao、Laura M. Bohn、Alexandros Makriyannis、Zhi-Jie Liu

  DOI：10.1016/j.cell.2020.01.008

  日期：2020.2

  Human endocannabinoid systems modulate multiple physiological processes mainly through the activation of cannabinoid receptors CB1 and CB2. Their high sequence similarity, low agonist selectivity, and lack of activation and G protein-coupling knowledge have hindered the development of therapeutic applications. Importantly, missing structural information has significantly held back the development of promising CB2-selective agonist drugs for treating inflammatory and neuropathic pain without the psychoactivity of CB1. Here, we report the cryoelectron microscopy structures of synthetic cannabinoid-bound CB2 and CB1 in complex with G(i), as well as agonist-bound CB2 crystal structure. Of important scientific and therapeutic benefit, our results reveal a diverse activation and signaling mechanism, the structural basis of CB2-selective agonists design, and the unexpected interaction of cholesterol with CB1, suggestive of its endogenous allosteric modulating role.