euglobal G3

• 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: euglobal G3
• 英文别名: Euglobal-G3；(1'R,2R,5'S)-5,7-dihydroxy-6',6'-dimethyl-6-(3-methylbutanoyl)spiro[3,4-dihydrochromene-2,2'-bicyclo[3.1.1]heptane]-8-carbaldehyde
• 化学式: C₂₃H₃₀O₅
• 分子量: 386.488
• InChiKey: XREJXBXJCWWRFP-OLJPZDALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  formyl isovaleryl phloroglucinol 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 4.0h， 生成 euglobal G3
  参考文献：
  名称：

  Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues

  摘要：

  In the present communication, naturally occurring phloroglucinol-monoterpene adducts, euglobals G1-G4 (3b/a and 4a/b) and 16 new analogues (13a/b-18a/b and 19-22) were synthesized by biomimetic approach. These synthetic compounds differ from natural euglobals in the nature of monoterpene and acyl functionality. All of these compounds were evaluated for their antibacterial, antifungal, antileishmanial and antimalarial activities. Analogue 17b possessed good antibacterial activity against methicillin-resistant Staphylococcus aureus, while analogues 19-22 possessed potent antifungal activity against Candida glabrata with IC(50)s ranging from 1.5 to 2.5 mu g/mL. Euglobals along with all synthesized analogues exhibited antileishmanial activity. Amongst these, euglobal G2 (3a), G3 (4a) and analogues 13a and 14a showed potent antileishmanial activity with IC50s ranging from 2.8 to 3.9 mu g/mL. Analogue 16a possessed antimalarial activity against chloroquine sensitive D6 clone of Plasmodium falciparum. None of the compounds showed toxicity against mammalian kidney fibroblasts (vero cells) upto the concentration of 4.76 mu g/ml. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.027

文献信息

• Electrochemical synthesis of euglobal-G1, -G2, -G3, -G4, -T1 and -IIc
  作者：Kazuhiro Chiba、Takaaki Arakawa、Masahiro Tada

  DOI：10.1039/a802306i

  日期：——

  Six natural euglobals were synthesized by electrochemical methods. In a key step, cycloaddition between in situ generated quinomethanes and terpenes was performed on the surface of PTFE-fibre coated electrode to give natural products using 2,3-dichloro-5,6-dicyano-p-hydroquinone (DDQH2) as a redox mediator. In this reaction system, biomimetic generation and cycloaddition of the unstable quinomethanes were efficiently completed by the selective oxidation of cresol derivatives.

  通过电化学方法合成了六种天然尤格洛布林。关键步骤是在聚四氟乙烯纤维涂层电极表面，现场生成的喹诺甲烷与萜类化合物进行环加成反应，以2,3-二氯-5,6-二氰基对苯二酚（DDQH2）作为氧化还原介质，得到天然产物。在该反应体系中，通过对甲酚衍生物的选择性氧化，高效地完成了不稳定喹诺甲烷的仿生生成和环加成反应。
• Synthesis of euglobal-G3 and -G4
  作者：Kazuhiro Chiba、Takaaki Arakawa、Masahiro Tada

  DOI：10.1039/cc9960001763

  日期：——

  The first, concise synthesis of euglobals is accomplished by biomimetic cycloaddition of β-pinene and quinone methides generated by oxidation of grandinol.

  首个简洁的尤戈全球合成是通过生物仿制的环加成反应，使用由格兰迪烯氧化生成的β-松油烯和醌烯醇。
• Plants extracts for use in brain modulation
  申请人：InterMed Discovery GmbH

  公开号：EP1939166A1

  公开（公告）日：2008-07-02

  Compounds obtainable from plants, e.g. of the genus Eucalyptus, or from microorganisms are shown to be useful as CNS activity modulators useful e.g. in the treatment of depression, for lifting mood and/or for increasing behavioural initiative and the like. This use and related aspects form embodiments of the invention. Also compounds as such are presented. The compounds useful are acylphloroglucine derivatives of the formula I, wherein the substituents are as defined in the description.

  从植物（如桉树属）或微生物中提取的化合物可用作中枢神经系统活性调节剂，例如用于治疗抑郁症、改善情绪和/或提高行为主动性等。这种用途和相关方面构成了本发明的实施例。此外，还介绍了本发明的化合物。 有用的化合物是式 I 的酰基氯葡萄糖衍生物、 其中的取代基如描述中所定义。
• PLANTS EXTRACTS FOR USE IN BRAIN MODULATION
  申请人：InterMed Discovery GmbH

  公开号：EP2061743A1

  公开（公告）日：2009-05-27
• PLANT EXTRACTS FOR USE IN BRAIN MODULATION
  申请人：Roemer Ernst

  公开号：US20120058172A1

  公开（公告）日：2012-03-08

  Compounds obtainable from plants, e.g. of the genus Eucalyptus, or from microorganisms are shown to be useful as CNS activity modulators useful e.g. in the treatment of depression, for lifting mood and/or for increasing behavioural initiative and the like. This use and related aspects form embodiments of the invention. Also compounds as such are presented. The compounds useful are acylphloroglucine derivatives of the formula I, wherein the substituents are as defined in the description.