(1'R,2'R)-4-heptyl-5'-methyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol | 55824-13-0

• 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
• 英文名称: (1'R,2'R)-4-heptyl-5'-methyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol
• 英文别名: (-)-trans-CBDP；(-)-trans-cannabidiphorol；5-heptyl-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-1,3-benzenediol；5-heptyl-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol
• CAS: 55824-13-0
• 化学式: C₂₃H₃₄O₂
• 分子量: 342.522
• InChiKey: GGHRHCGOMWNLCE-VQTJNVASSA-N

物化性质

• 沸点：
  488.1±45.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50mg/mL； DMSO：60mg/mL； DMSO:PBS (pH 7.2) (1:3)：0.25 mg/ml；乙醇：35mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• 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：

  (1'R,2'R)-4-heptyl-5'-methyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到(6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  C1‘-Cycloalkyl Side Chain Pharmacophore in Tetrahydrocannabinols

  摘要：

  In earlier work we have provided evidence for the presence of a subsite within the CB1 and CB2 cannabinoid receptor binding domains of classical cannabinoids. This putative subsite corresponds to substituents on the C1'-position of the C3-alkyl side chain, a key pharmacophoric feature in this class of compounds. We have now refined this work through the synthesis of additional C1'-cycloalkyl compounds using newly developed approaches. Our findings indicate that the C1'-cyclopropyl and C1'-cyclopentyl groups are optimal pharmacophores for both receptors while the C1'-cyclobutyl group interacts optimally with CB1 but not with CB2. The C1'-cyclohexyl analogs have reduced affinities for both CB1 and CB2. However, these affinities are significantly improved with the introduction of a C2'-C3' cis double bond that modifies the available conformational space within the side chain and allows for a better accommodation of a six-membered ring within the side chain subsite. Our SAR results are highlighted by molecular modeling of key analogs.

  DOI：

  10.1021/jm070121a
• 作为产物：
  描述：

  5-n-heptyl resorcinol dimethyl ether 在 三溴化硼 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (1'R,2'R)-4-heptyl-5'-methyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol
  参考文献：
  名称：

  C1‘-Cycloalkyl Side Chain Pharmacophore in Tetrahydrocannabinols

  摘要：

  In earlier work we have provided evidence for the presence of a subsite within the CB1 and CB2 cannabinoid receptor binding domains of classical cannabinoids. This putative subsite corresponds to substituents on the C1'-position of the C3-alkyl side chain, a key pharmacophoric feature in this class of compounds. We have now refined this work through the synthesis of additional C1'-cycloalkyl compounds using newly developed approaches. Our findings indicate that the C1'-cyclopropyl and C1'-cyclopentyl groups are optimal pharmacophores for both receptors while the C1'-cyclobutyl group interacts optimally with CB1 but not with CB2. The C1'-cyclohexyl analogs have reduced affinities for both CB1 and CB2. However, these affinities are significantly improved with the introduction of a C2'-C3' cis double bond that modifies the available conformational space within the side chain and allows for a better accommodation of a six-membered ring within the side chain subsite. Our SAR results are highlighted by molecular modeling of key analogs.

  DOI：

  10.1021/jm070121a

文献信息

• [EN] CATALYTIC CANNABINOID PROCESSES AND PRECURSORS<br/>[FR] PROCÉDÉS ET PRÉCURSEURS DE CANNABINOÏDES CATALYTIQUES
  申请人：KARE CHEMICAL TECH INC

  公开号：WO2020232545A1

  公开（公告）日：2020-11-26

  The present disclosure relates to new cannabinoid sulfonate esters and processes for their use to prepare cannabinoids. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabinoids from the cannabinoid sulfonate esters.

  本公开涉及新的大麻素磺酸酯和它们的制备大麻素的过程。该公开还涉及使用催化剂和催化过程从大麻素磺酸酯制备大麻素。
• CANNABIS EXTRACTS AND USES THEREOF
  申请人：Consiglio Nazionale delle Ricerche

  公开号：US20220064090A1

  公开（公告）日：2022-03-03

  The present disclosure concerns a group of cannabinoid compounds defined by formulas (I) to (IV), wherein R 1 is —H or —COOH, for the first time isolated and fully characterized in structure, absolute stereochemistry by the present applicant. Methods of isolation, characterization, stereoselective synthesis, biological activity, pharmaceutical compositions and therapeutic applications of the present compounds as modulators of the cannabinoid CB1 receptor are also object of the disclosure.

  本公开涉及一组由公式（I）到（IV）定义的大麻素化合物，其中R1为—H或—COOH，并且这些化合物由本申请人首次分离并完全确定了结构和绝对立体化学。本公开还涉及本化合物的分离、表征、立体选择性合成、生物活性、制药组合物以及作为大麻素CB1受体调节剂的治疗应用的方法。
• [EN] METHOD FOR SELECTIVE SEPARATION, ISOLATION AND RECOVERY OF CANNABIDIOL AND CANNABIDIOL-LIKE MEROTERPENE ACIDS FROM COMPLEX MATRICES<br/>[FR] PROCÉDÉ DE SÉPARATION, D'ISOLEMENT ET DE RÉCUPÉRATION SÉLECTIFS DE CANNABIDIOL ET D'ACIDES MÉROTERPÉNIQUES DE TYPE CANNABIDIOL À PARTIR DE MATRICES COMPLEXES
  申请人：NAHTIGAL ISTOK

  公开号：WO2020160652A1

  公开（公告）日：2020-08-13

  Described is a method of selectively isolating non-rigid structure meroterpenes (for example, cannabidiolic acid) from a complex matrix that may also contain rigid structure meroterpenes (for example, THCa), comprising selectively precipitating the non-rigid structure meroterpenes in the form of a triethylamine salt complex by adding triethylamine; isolating the triethylamine salt complex from the mother liquor; then heating the triethylamine salt complex to vaporize the triethylamine, leaving an isolated neutral non-rigid structure meroterpene. In certain embodiments, the starting product is a cannabis resin that has been solubilized in, for example, d-limonene.

  描述了一种从可能还包含刚性结构的多萜类化合物（例如THCa）的复杂基质中选择性分离非刚性结构多萜类化合物（例如大麻二酸）的方法，包括通过添加三乙胺选择性地沉淀非刚性结构多萜类化合物形成三乙胺盐络合物；从母液中分离出三乙胺盐络合物；然后加热三乙胺盐络合物以蒸发三乙胺，留下一个孤立的中性非刚性结构多萜类化合物。在某些实施例中，起始产品是已溶解在例如d-柠檬烯中的大麻树脂。
• ANGIOGENIC RESORCINOL DERIVATIVES
  申请人：Makriyannis Alexandros

  公开号：US20120172339A1

  公开（公告）日：2012-07-05

  Novel resorcinol derivatives and methods of preparation and use are presented. These compounds can stimulate angiogenesis as a biological function triggered by the activation of one cannabinoid receptor distinct from CB1 and CB2. Thus, these compounds are specific ligands for one cannabinoid receptor distinct from CB1 and CB2. 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.

  本发明提供了新型间苯二酚衍生物的制备方法和用途。这些化合物可以刺激血管生成，作为一种由激活与CB1和CB2不同的一种大麻素受体而触发的生物学功能。因此，这些化合物是与CB1和CB2不同的一种大麻素受体的特异性配体。当以治疗有效量的方式向个体或动物施用这些发明化合物时，会在个体或动物中产生足够高的该化合物水平，从而引起生理反应。这种生理反应可能有助于治疗许多生理状况。
• [EN] CBD CANNABINOIDS AND CBD CANNABINOID ANALOGUES<br/>[FR] CANNABINOÏDES CBD ET ANALOGUES DE CANNABINOÏDES CBD
  申请人：BOTANIX PHARMACEUTICALS LTD

  公开号：WO2022133544A1

  公开（公告）日：2022-06-30

  Cannabidiol (CBD) cannabinoids and CBD cannabinoid analogues with, inter alia, antimicrobial activity, synthetic methods for the preparation thereof and medical uses and formulations containing same.

  大麻二酚（CBD）大麻素及CBD类似物具有抗微生物活性，其制备的合成方法以及含有其的医疗用途和制剂。