4-苯基-5,7-二羟基-6-(3-甲基丁酰基)-8-(3-甲基-2-丁烯基)-2H-1-苯并吡喃-2-酮 | 18483-64-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 中文名称: 4-苯基-5,7-二羟基-6-(3-甲基丁酰基)-8-(3-甲基-2-丁烯基)-2H-1-苯并吡喃-2-酮
• 中文别名: 5,7-二羟基-6-(3-甲基丁酰)-8-(3-甲基丁-2-烯-1-基)-4-苯基-2H-色烯-2-酮
• 英文名称: mammeisin
• 英文别名: 5,7-dihydroxy-6-(3-methylbutanoyl)-8-(3-methylbut-2-enyl)-4-phenyl-2H-chromen-2-one；mammea A/AA；4-phenyl-5,7-dihydroxy-6-(3-methylbutanoyl)-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one；5,7-dihydroxy-8-(3-methyl-but-2-enyl)-6-(3-methyl-butyryl)-4-phenyl-chromen-2-one；5,7-dihydroxy-6-isovaleryl-8-(3-methyl-but-2-enyl)-4-phenyl-coumarin；5,7-Dihydroxy-6-isovaleryl-8-(3-methyl-but-2-enyl)-4-phenyl-cumarin；5,7-dihydroxy-6-(3-methylbutanoyl)-8-(3-methylbut-2-enyl)-4-phenylchromen-2-one
• CAS: 18483-64-2
• 化学式: C₂₅H₂₆O₅
• 分子量: 406.478
• InChiKey: JIFOADIANOIMSK-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  98-109°C

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-苯基-5,7-二羟基-6-(3-甲基丁酰基)-8-(3-甲基-2-丁烯基)-2H-1-苯并吡喃-2-酮 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到4-phenyl-5-hydroxy-6-(3-methyl-1-oxobutyl)-2'-(1-hydroxy-1-methylethyl)-3',4'-dihydro(5',4':7,8)furanocoumarin
  参考文献：
  名称：

  mammeins和surangin a的合成

  摘要：

  据报道，天然的4-烷基和4-芳基香豆素与六取代的芳环（氧化磷酸化的解偶联剂）的合成。合成的Mammea B / BB是（S）-（-）-化合物。

  DOI：

  10.1016/s0040-4039(00)98874-9
• 作为产物：
  描述：

  异戊酰氯 在 氢氧化钾 、 三氯化铝 、 硫酸 作用下， 以 二硫化碳 、 硝基甲烷 、 水 、 溶剂黄146 为溶剂， 生成 4-苯基-5,7-二羟基-6-(3-甲基丁酰基)-8-(3-甲基-2-丁烯基)-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  mammeins和surangin a的合成

  摘要：

  据报道，天然的4-烷基和4-芳基香豆素与六取代的芳环（氧化磷酸化的解偶联剂）的合成。合成的Mammea B / BB是（S）-（-）-化合物。

  DOI：

  10.1016/s0040-4039(00)98874-9

文献信息

• Methods and compositions for lowering levels of blood lipids
  申请人：Pharmacia Corporation

  公开号：US20040014806A1

  公开（公告）日：2004-01-22

  Disclosed are methods to lower blood cholesterol levels or inhibit ileal apical sodium co-dependent bile acid transport (ASBT) protein using coumarin and anthracene dione derivatives. Pharmaceutical compositions are also disclosed.

  揭示了使用香豆素和蒽醌二酮衍生物降低血液胆固醇水平或抑制回肠顶端钠依赖性胆汁酸转运蛋白（ASBT）的方法。同时还公开了相关的药物组合物。
• PLANT EXTRACT OBTAINED FROM KIELMEYERA AUREOVINOSA WHICH HAS ANTIBIOTIC ACTIVITY, ISOLATED CHEMICAL COMPOUND, COMPOSITIONS COMPRISING SAME, USES THEREOF AND METHODS FOR PREVENTING AND TREATING BACTERIAL INFECTIONS
  申请人：Extracta Moléculas Naturais S/A

  公开号：EP2735311A1

  公开（公告）日：2014-05-28

  The present invention refers primarily to a plant extract obtained from Kielmeyera aureovinosa which has accentuated antibiotic activity. In a second modality, the invention describes a new chemical compound isolated from the same, as well as variations thereof. In other terms, the present invention provides compositions comprising a phytotherapic obtained from said plant extract, as well as veterinary pharmaceutical compositions comprising isolated compounds and variations of the same. Additionally, the present invention provides uses of the plant extract, chemical compounds and compositions comprising the same for the preparation of medicines for the prevention or treatment of bacterial infections, as well as methods of prevention or treatment of the same.

  本发明主要涉及一种从 Kielmeyera aureovinosa 中提取的植物提取物，它具有更强的抗生素活性。在第二种模式中，本发明描述了从该提取物中分离出来的一种新化合物及其变体。换言之，本发明提供了包含从上述植物提取物中获得的植物治疗剂的组合物，以及包含分离化合物及其变体的兽药组合物。 此外，本发明还提供了植物提取物、化合物和包含上述物质的组合物在制备预防或治疗细菌感染的药物中的用途，以及预防或治疗细菌感染的方法。
• Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors
  作者：Jean-Jacques Helesbeux、Olivier Duval、Caroline Dartiguelongue、Denis Séraphin、Jean-Michel Oger、Pascal Richomme

  DOI：10.1016/j.tet.2004.01.033

  日期：2004.3

  Application of our original photooxidation-reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising phenolic assistance effect. We also showed that ortho-(3-hydroxy-3-methylbut-1-enyl)phenol derivatives could be considered as biogenetic precursors of 2,2-dimethylbenzopyranic structures. (C) 2004 Elsevier Ltd. All rights reserved.
• Crombie, Leslie; Jones, Raymond C. F.; Palmer, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 317 - 332
  作者：Crombie, Leslie、Jones, Raymond C. F.、Palmer, Christopher J.

  DOI：——

  日期：——
• Characterization of Mammea A/AA in solution and in interaction with β-cyclodextrin: UV–visible spectroscopy, cyclic voltammetry and DFT-TDDFT/MD study
  作者：Baruch A. Ateba、Daniel Lissouck、Anatole Azébazé、Christophe Thiery Ebelle、Achille Nassi、Emmanuel Ngameni、Guy Duportail、Luc Mbazé、Cyril A. Kenfack

  DOI：10.1016/j.molliq.2015.11.006

  日期：2016.1

  Mammea A/AA (MA) was recently introduced as a new anticancer, antioxidant and antimicrobial compound, but presenting some cellular toxicity. In this work, MA in solution and interacting with beta-cyclodextrin (beta-CD) was characterized by UV-visible absorption spectroscopy, cyclic voltammetry and theoretical density functional theory (DFT), time dependent density functional theory (TDDFT) calculations and molecular dynamic (MD) simulation. We found that the absorbance of this compound was governed by the relative wavelength position of its charge transfer (Cl) and locally excited (LE) states, which are respectively sensitive to polarity and H-bonding. Comparison of the spectroscopy of MA in solution and in presence of increasing amount of (beta-CD was showing a systematic blue shift and hyperchromic effect, while a decrease of the voltammetry signal peak was observed, which we attributed to the formation of an inclusion complex with beta-CD. A binding constant of 7.2 x 10(4) M-1 was estimated and the stoichiometry of the complex was found to be 1:1. Theoretical calculations have shown that this complex does not affect the antioxidant potency of MA and that the structure of beta-CD complex is stabilized by two H-bonds between MA carbonyl groups and the beta-CD wider rim hydroxyl groups, as well as attractive Van der Waals forces. These results suggest that the binding of MA to beta-CD is strong enough and hence allowing this compound to be stored and carried by beta-CD for in vivo loading. (C) 2015 Elsevier B.V. All rights reserved.