前大麻酚苯乙酯 | 1040411-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 前大麻酚苯乙酯
• 英文名称: pre-cannabigerol phenethyl ester
• 英文别名: 2-phenylethyl 3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxy-6-pentylbenzoate
• CAS: 1040411-86-6
• 化学式: C₃₀H₄₀O₄
• 分子量: 464.645
• InChiKey: OXZHQCKVHXGGJK-HAVVHWLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙醇 、 大麻萜酚酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以32%的产率得到前大麻酚苯乙酯
  参考文献：
  名称：

  Antibacterial Cannabinoids from Cannabis sativa: A Structure−Activity Study

  摘要：

  Marijuana (Cannabis sativa) has long been known to contain antibacterial cannabinoids, whose potential to address antibiotic resistance has not yet been investigated. All five major cannabinoids (cannabidiol (1b), cannabichromene (2), cannabigerol (3b), Delta(9)-tetrahydrocannabinol (4b), and cannabinol (5)) showed potent activity against a variety of methicillin-resistant Staphylococcus aureus (MRSA)strains Of Current clinical relevance. Activity was remarkably tolerant to the nature of the prenyl moiety, to its relative position compared to the n-pentyl moiety (abnormal cannabinoids), and to carboxylation of the resorcinyl moiety (pre-cannabinoids). Conversely, methylation and acetylation of the phenolic hydroxyls, esterification of the carboxylic group of pre-cannabinoids, and introduction of a second prenyl moiety were all detrimental for antibacterial activity. Taken together, these observations Suggest that the prenyl moiety of cannabinoids serves mainly as a modulator of lipid affinity for the olivetol core, a per se poorly active antibacterial pharmacophore, while their high potency definitely Suggests a specific, but yet elusive, mechanism of activity.

  DOI：

  10.1021/np8002673

文献信息

• Antibacterial Cannabinoids from <i>Cannabis sativa</i>: A Structure−Activity Study
  作者：Giovanni Appendino、Simon Gibbons、Anna Giana、Alberto Pagani、Gianpaolo Grassi、Michael Stavri、Eileen Smith、M. Mukhlesur Rahman

  DOI：10.1021/np8002673

  日期：2008.8.1

  Marijuana (Cannabis sativa) has long been known to contain antibacterial cannabinoids, whose potential to address antibiotic resistance has not yet been investigated. All five major cannabinoids (cannabidiol (1b), cannabichromene (2), cannabigerol (3b), Delta(9)-tetrahydrocannabinol (4b), and cannabinol (5)) showed potent activity against a variety of methicillin-resistant Staphylococcus aureus (MRSA)strains Of Current clinical relevance. Activity was remarkably tolerant to the nature of the prenyl moiety, to its relative position compared to the n-pentyl moiety (abnormal cannabinoids), and to carboxylation of the resorcinyl moiety (pre-cannabinoids). Conversely, methylation and acetylation of the phenolic hydroxyls, esterification of the carboxylic group of pre-cannabinoids, and introduction of a second prenyl moiety were all detrimental for antibacterial activity. Taken together, these observations Suggest that the prenyl moiety of cannabinoids serves mainly as a modulator of lipid affinity for the olivetol core, a per se poorly active antibacterial pharmacophore, while their high potency definitely Suggests a specific, but yet elusive, mechanism of activity.