1-(2-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxy-phenyl)-2-methylbutan-1-one | 1131366-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxy-phenyl)-2-methylbutan-1-one
• 英文别名: olympicin A；2-geranyloxy-1-(2-methylbutanoyl)phloroglucinol；1,5-dihydroxy-2-(2'-methylbutanoyl)-3-(3,7-dimethyl-2,6-octadienyl)-benzene；1-[2-[(2E)-3,7-dimethylocta-2,6-dienoxy]-4,6-dihydroxy-phenyl]-2-methyl-butan-1-one；1-[2-[(2E)-3,7-dimethylocta-2,6-dienoxy]-4,6-dihydroxyphenyl]-2-methylbutan-1-one
• CAS: 1131366-93-2
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: UMIJNJJRYSRDPG-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以110 mg的产率得到1-(2-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxy-phenyl)-2-methylbutan-1-one
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationship Studies, and Antibacterial Evaluation of 4-Chromanones and Chalcones, as Well as Olympicin A and Derivatives

  摘要：

  On the basis of recently reported abyssinone II and olympicin A, a series of chemically modified flavonoid phytochemicals were synthesized and evaluated against Mycobacterium tuberculosis and a panel of Gram-positive and -negative bacterial pathogens. Some of the synthesized compounds exhibited good antibacterial activities against Gram-positive pathogens including methicillin resistant Staphylococcus aureus with minimum inhibitory concentration as low as 0.39 mu g/mL. SAR analysis revealed that the 2-hydrophobic substituent and the 4-hydrogen bond donor/acceptor of the 4-chromanone scaffold together with the hydroxy groups at 5- and 7-positions enhanced antibacterial activities; the 2',4'-dihydroxylated A ring and the lipophilic substituted B ring of chalcone derivatives were pharmacophoric elements for antibacterial activities. Mode of action studies performed on selected compounds revealed that they dissipated the bacterial membrane potential, resulting in the inhibition of macromolecular biosynthesis; further studies showed that selected compounds inhibited DNA topoisomerase IV, suggesting complex mechanisms of actions for compounds in this series.

  DOI：

  10.1021/jm500853v

文献信息

• Anti-Bacterial Agents
  申请人：Gibbons Simon

  公开号：US20100222426A1

  公开（公告）日：2010-09-02

  The invention relates to novel acylphloroglucinols which have strong growth inhibitory effects on multi-drug resistant strains of bacteria, particularly MRSA. Typically the compounds have a terpene substituent, or a terpene-derived substituent. Methods of isolating the compounds from natural sources, and synthetic methods for forming the compounds are also provided.

  这项发明涉及新型酰基苯酚萜类化合物，对多药耐药菌株，尤其是MRSA具有强烈的生长抑制作用。通常这些化合物具有萜类取代基或萜类衍生取代基。同时还提供了从天然来源分离这些化合物的方法，以及合成这些化合物的方法。
• [EN] ANTI-BACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTÉRIENS
  申请人：UNIV LONDON PHARMACY

  公开号：WO2009034346A2

  公开（公告）日：2009-03-19

  The invention relates to novel acylphloroglucinols which have strong growth inhibitory effects on multi-drug resistant strains of bacteria, particularly MRSA. Typically the compounds have a terpene substituent, or a terpene- derived substituent. Methods of isolating the compounds from natural sources, and synthetic methods for forming the compounds are also provided.