5-(1,1-二甲基庚基)-2-[(1R,6R)-3-甲基-6-(1-甲基乙烯基)-2-环己烯-1-基]-1,3-苯二醇 | 97452-63-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 5-(1,1-二甲基庚基)-2-[(1R,6R)-3-甲基-6-(1-甲基乙烯基)-2-环己烯-1-基]-1,3-苯二醇
• 中文别名: 5-(1-甲基-5-(三氟甲基)-1H-吡唑-3-基)噻吩-2-羧酸
• 英文名称: (-)-5′-cannabidiol-dimethylheptyl
• 英文别名: HU 219；5-(1,1-Dimethylheptyl)-2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-1,3-benzenediol；5-(2-methyloctan-2-yl)-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol
• CAS: 97452-63-6
• 化学式: C₂₅H₃₈O₂
• 分子量: 370.576
• InChiKey: MPJURNPNPDQYSY-LEWJYISDSA-N

物化性质

• 沸点：
  502.1±50.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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-(1,1-二甲基庚基)-2-[(1R,6R)-3-甲基-6-(1-甲基乙烯基)-2-环己烯-1-基]-1,3-苯二醇 在 platinum(IV) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 生成 5-(2-methyloctan-2-yl)-2-[(1R,2S)-5-methyl-2-propan-2-ylcyclohexyl]benzene-1,3-diol
  参考文献：
  名称：

  New Cannabidiol Derivatives:  Synthesis, Binding to Cannabinoid Receptor, and Evaluation of Their Antiinflammatory Activity

  摘要：

  Cannabidiol (CBD) and cannabidiol dimethyl hephtyl (CBD-DMH) were hydrogenated to give four different epimers. The new derivatives were evaluated for their ability to modulate the production of reactive oxygen intermediates (ROI), nitric oxide (NO), and tumor necrosis factor (TNF-alpha) by murine macrophages, and for their binding to the cannabinoid receptor (C,). Surprisingly, we found that these derivatives exhibit good binding to CB1. In addition hydrogenated CBD and CBD-DMH demonstrate bioactivities different from their original compounds.

  DOI：

  10.1021/jm050709m
• 作为产物：
  描述：

  反式-薄荷基-2,8-二烯-1-醇 、 5-(1,1-二甲基庚基)间苯二酚 在 aluminum oxide 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到5-(1,1-二甲基庚基)-2-[(1R,6R)-3-甲基-6-(1-甲基乙烯基)-2-环己烯-1-基]-1,3-苯二醇
  参考文献：
  名称：

  三氟硼化硼在乙醚上的醚化反应-一种改良的路易斯酸试剂。：大麻二酚的改进合成

  摘要：

  氧化铝上的三氟化硼醚化物催化间苯二酚，单甲基间苯二酚与几种单萜烯丙基烯丙醇的缩合：与三氟化硼醚化物在溶液中的平行反应相反，所得产物不进行进一步的环化。

  DOI：

  10.1016/s0040-4039(00)98518-6

文献信息

• [EN] CANNABINOID DERIVATIVES<br/>[FR] DÉRIVÉS CANNABINOÏDES
  申请人：CANOPY GROWTH CORP

  公开号：WO2021000053A1

  公开（公告）日：2021-01-07

  The present invention provides cannabinoid derivatives, a pharmaceutical composition comprising said derivative and a method of using said derivatives in treating or preventing a disease associated with cannabinoid receptors. The claimed cannabinoid derivatives are described by the following formula or an enantiomer, diastereomer, racemate, tautomer, or metabolite thereof, or a pharmaceutically acceptable salt, solvate or hydrate of the compound.

  本发明提供了大麻素衍生物，包括所述衍生物的药物组合物以及使用所述衍生物治疗或预防与大麻素受体相关的疾病的方法。所述申请的大麻素衍生物由以下公式或其对映体、二对映体、消旋体、互变异构体或代谢物，或该化合物的药用可接受盐、溶剂合物或水合物描述。
• Enantiomeric cannabidiol derivatives: synthesis and binding to cannabinoid receptors
  作者：Lum�r O. Hanu?、Susanna Tchilibon、Datta E. Ponde、Aviva Breuer、Ester Fride、Raphael Mechoulam

  DOI：10.1039/b416943c

  日期：——

  (−)-Cannabidiol (CBD) is a major, non psychotropic constituent of cannabis. It has been shown to cause numerous physiological effects of therapeutic importance. We have reported that CBD derivatives in both enantiomeric series are of pharmaceutical interest. Here we describe the syntheses of the major CBD metabolites, (−)-7-hydroxy-CBD and (−)-CBD-7-oic acid and their dimethylheptyl (DMH) homologs, as well as of the corresponding compounds in the enantiomeric (+)-CBD series. The starting materials were the respective CBD enantiomers and their DMH homologs. The binding of these compounds to the CB1 and CB2 cannabinoid receptors are compared. Surprisingly, contrary to the compounds in the (−) series, which do not bind to the receptors, most of the derivatives in the (+) series bind to the CB1 receptor in the low nanomole range. Some of these compounds also bind weakly to the CB2 receptor.

  (-)-大麻二酚（CBD）是大麻中一种主要的非精神药物成分。它已被证明能产生许多具有治疗意义的生理效应。我们曾报道过两种对映体系列的大麻二酚衍生物都具有药用价值。在此，我们介绍了主要的 CBD 代谢物 (-)-7-hydroxy-CBD 和 (-)-CBD-7-oic acid 及其二甲基庚基 (DMH) 同系物以及 (+)-CBD 对映体系列中相应化合物的合成。起始材料为各自的 CBD 对映体及其 DMH 同系物。比较了这些化合物与 CB1 和 CB2 大麻受体的结合情况。令人惊讶的是，与不与受体结合的 (-) 系列化合物相反，(+) 系列的大多数衍生物与 CB1 受体的结合力都在低纳摩尔范围内。其中一些化合物还与 CB2 受体有微弱的结合。
• [EN] FLOURINATED CBD COMPOUNDS, COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSÉS DE CBD FLUORÉS, COMPOSITIONS ET LEURS UTILISATIONS
  申请人：YISSUM RES DEV CO OF HEBREW UNIV JERUSALEM LTD

  公开号：WO2017008136A3

  公开（公告）日：2017-11-16
• Cannabinol Derivatives:  Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase
  作者：Man-Hee Rhee、Zvi Vogel、Jacob Barg、Michael Bayewitch、Rivka Levy、Lumir Hanuš、Aviva Breuer、Raphael Mechoulam

  DOI：10.1021/jm970126f

  日期：1997.9.1

  Several derivatives of cannabinol anti the 1,1-dimethylheptyl homolog (DMM) of cannabinol were prepared and assayed for binding to the brain and the peripheral cannabinoid receptors (CB1 and CB2), as well as for activation of CB1- and CB2-mediated inhibition of adenylylcyclase. The DMH derivatives were much more potent than the pentyl (i.e., cannabinol) derivatives. 11-Hydroxycannabinol (4a) was found to bind potently to both CB1 and CB2 (K-i values of 38.0 +/- 7.2 and 26.6 +/- 5.5 nM, respectively) and to inhibit CB1-mediated adenylylcyclase with an EC50 of 58.1 +/- 6.2 nM but to cause only 20% inhibition of CB2-mediated adenylylcyclase at 10 mu M. It behaves as a specific, though not potent, CB2 antagonist. 11-Hydroxycannabinol-DMH (4b) is a very potent agonist for both CB1 and CB2 (K-i values of 100 +/- 50 and 200 +/- 40 pM; EC50 of adenylylcyclase inhibition 56.2 +/- 4.2 and 207.5 +/- 27.8 pM, respectively).
• COMPOSITIONS AND METHODS FOR TREATMENT OF OCULAR INFLAMMATION AND/OR PAIN
  申请人：LYNCH MARY

  公开号：US20150258040A1

  公开（公告）日：2015-09-17

  The disclosure provides methods of treatment of ocular inflammation and/or neuropathic pain in a subject in need thereof, comprising administering to the subject in need thereof a CB2 target agent, a cannabimimetic agent or a combination thereof. The agent is optionally a cannabinoid, such as a non-psychotropic cannabinoid or a synthetic cannabinoid. In certain embodiments, the non-psychotropic phytocannabinoid is β-caryophyllene or cannabidiol [CBD] and the synthetic cannabinoid is HU-433, HU-308, or a modified CBD such as CBD-DMH. In methods of the disclosure, CBD-DMH is optionally administered in combination with a further CB2 target agent or cannabimimetic agent. The disclosure also provides ocular pharmaceutical compositions containing the CB2 target agents and/or cannabimimetic agents described herein.