(2S)-1-(2-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxy-phenyl)-2-methylbutan-1-one | 1131366-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-1-(2-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxy-phenyl)-2-methylbutan-1-one
• 英文别名: (S,E)-1-(2-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxyphenyl)-2-methylbutan-1-one；olympicin A；(S)-4,6-dihydroxy-2-O-(3'',7''-dimethyl-2'',6''-octadienyl)-1-(2'-methylbutanoyl)benzene；(S)-1-(2-geranyloxy-4,6-dihydroxyphenyl)butan-1-one；(2S)-1-[2-[(2E)-3,7-dimethylocta-2,6-dienoxy]-4,6-dihydroxyphenyl]-2-methylbutan-1-one
• CAS: 1131366-95-4
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: UMIJNJJRYSRDPG-KMPOOHAWSA-N

物化性质

• 沸点：
  497.5±45.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

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：

  (S)-(+)-(2-methylbutyryl)phloroglucinol 在 咪唑 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.09h， 生成 (2S)-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：

  酰基金葡糖醇的全合成及其对金黄色葡萄球菌多药耐药（MDR）和耐甲氧西林菌株的临床分离株的抗菌活性

  摘要：

  以生物测定为导向的药物发现工作着眼于金丝桃属的各种物种，导致发现了许多新的酰基间苯三酚，包括（S，E）-1-（2-（（3,7-dimethylocta-2,6-dien-来自H的1-基）氧基）-4,6-二羟基苯基）-2-甲基丁-1--1-酮（6，奥比汀A）。olympicum，与MIC值范围为0.5至1mg / L与一系列多药耐药（MDR）和耐甲氧西林的临床分离株的金黄色葡萄球菌（MRSA）菌株。奥林匹克霉素A的有前途的活性和有趣的化学反应促使我们进行6的全合成以及一系列类似物，以评估它们作为一组新的抗菌剂的结构活性特征。以下的合成6和结构上相关的acylphloroglucinols 7 - 15和18 - 24，其对一组抗细菌活性的金黄色葡萄球菌菌株进行评价。在间苯三酚核心上，由一个8至10个碳原子邻位至一个5个碳原子的酰基取代基组成的烷氧基的存在是重要的结构特征，有望实现抗葡萄球菌的活性。

  DOI：

  10.1016/j.ejmech.2018.05.038

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。
• Synthesis, Structure–Activity Relationship Studies, and Antibacterial Evaluation of 4-Chromanones and Chalcones, as Well as Olympicin A and Derivatives
  作者：Li Feng、Marcus M. Maddox、Md. Zahidul Alam、Lissa S. Tsutsumi、Gagandeep Narula、David F. Bruhn、Xiaoqian Wu、Shayna Sandhaus、Robin B. Lee、Charles J. Simmons、Yuk-Ching Tse-Dinh、Julian G. Hurdle、Richard E. Lee、Dianqing Sun

  DOI：10.1021/jm500853v

  日期：2014.10.23

  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.
• Antibacterial Acylphloroglucinols from <i>Hypericum olympicum</i>
  作者：Winnie K. P. Shiu、M. Mukhlesur Rahman、Jonathan Curry、Paul Stapleton、Mire Zloh、John P. Malkinson、Simon Gibbons

  DOI：10.1021/np2003319

  日期：2012.3.23

  New antibacterial acylphloroglucinols (1-5) were isolated and characterized from the aerial parts of the plant Hypericum olympicum L. cf. uniflorum. The structures of these compounds were confirmed by extensive 1D- and 2D-NMR experiments to be 4,6-dihydroxy-2-O-(3 '',7 ''-dimethyl-2 '',6 ''-octadienyl)-1-(2 '-methylbutanoyl)benzene (1), 4,6-dihydroxy-2-O-(7 ''-hydroxy-3 '',7 ''-dimethyl-2 '',5 ''-octadienyl)-1-(2 '-methylbutanoyl)benzene (2), 4,6-dihydroxy-2-O-(6 ''-hydroxy-3 '',7 ''-dimethyl-2 '',7 ''-octadienyl)-1-(2 '-methylbutanoyl)benzene (3), 4,6-dihydroxy-2-O-(6 ''-hydroperoxy-3 '',7 ''-dimethyl-2 '',7 ''-octadienyl)-1-(2 '-methylbutanoyl)benzene (4), and 4,6-dihydroxy-2-O-(6 '',7 ''-epoxy-3 '',7 ''-dimethyloct-2 ''-enyl)-1-(2 '-methylbutanoyl)benzene (5). These new natural products have been given the trivial names olympicins A-E (1-5). All compounds were evaluated against a panel of methicillin-resistant Staph. aureus and multidrug-resistant strains of Staph. aureus. Compound 1 exhibited minimum inhibitory concentrations (MICs) of 0.5-1 mg/L against the tested Staph. aureus strains. Compounds 2 to 5 were also shown to be active, with MICs ranging from 64 to 128 mg/L. Compound 1 was synthesized using a simple four-step method that can be readily utilized to give a number of structural analogues of 1.
• [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.
• Total synthesis of acylphloroglucinols and their antibacterial activities against clinical isolates of multi-drug resistant (MDR) and methicillin-resistant strains of Staphylococcus aureus
  作者：M. Mukhlesur Rahman、Winnie K.P. Shiu、Simon Gibbons、John P. Malkinson

  DOI：10.1016/j.ejmech.2018.05.038

  日期：2018.7

  of olympicin A prompted us to carry out the total synthesis of 6 and a series of analogues in order to assess their structure-activity profile as a new group of antibacterial agents. Following the synthesis of 6 and structurally-related acylphloroglucinols 7–15 and 18–24, their antibacterial activities against a panel of S. aureus strains were evaluated. The presence of an alkyloxy group consisting

  以生物测定为导向的药物发现工作着眼于金丝桃属的各种物种，导致发现了许多新的酰基间苯三酚，包括（S，E）-1-（2-（（3,7-dimethylocta-2,6-dien-来自H的1-基）氧基）-4,6-二羟基苯基）-2-甲基丁-1--1-酮（6，奥比汀A）。olympicum，与MIC值范围为0.5至1mg / L与一系列多药耐药（MDR）和耐甲氧西林的临床分离株的金黄色葡萄球菌（MRSA）菌株。奥林匹克霉素A的有前途的活性和有趣的化学反应促使我们进行6的全合成以及一系列类似物，以评估它们作为一组新的抗菌剂的结构活性特征。以下的合成6和结构上相关的acylphloroglucinols 7 - 15和18 - 24，其对一组抗细菌活性的金黄色葡萄球菌菌株进行评价。在间苯三酚核心上，由一个8至10个碳原子邻位至一个5个碳原子的酰基取代基组成的烷氧基的存在是重要的结构特征，有望实现抗葡萄球菌的活性。