5,7-dihydroxy-3-(4-methoxyphenyl)-6-(3-methylbut-2-enyl)-4H-chromen-4-one | 27762-99-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5,7-dihydroxy-3-(4-methoxyphenyl)-6-(3-methylbut-2-enyl)-4H-chromen-4-one
• 英文别名: 4'methyl ether of wighteone；gancaonin A；5,7-dihydroxy-3-(4-methoxy-phenyl)-6-(3-methyl-but-2-enyl)-chromen-4-one；6-Prenyl-4'-methoxy-5,7-dihydroxy-isoflavon；6-Prenyl-4'-methoxy-5,7-dihydroxyisoflavon；5,7-dihydroxy-3-(4-methoxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one
• CAS: 27762-99-8
• 化学式: C₂₁H₂₀O₅
• 分子量: 352.387
• InChiKey: JQNSUDIGIIGIOL-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  213-217°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 为溶剂， 生成 5,7-dihydroxy-3-(4-methoxyphenyl)-6-(3-methylbut-2-enyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and Evaluation of Derrubone and Select Analogues

  摘要：

  [GRAPHICS]Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.

  DOI：

  10.1021/jo702366g

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Structure-activity relationship study of 4′-O-methylgrynullarin derivatives for the development of novel anticancer agents based on anti-austerity strategy
  作者：Nguyen Ngoc Thanh Luan、Takuya Okada、Ruka Arata、Lanke Prudhvi、Moe Miyaguchi、Yuri Kodama、Suresh Awale、Naoki Toyooka

  DOI：10.1016/j.tet.2022.132931

  日期：2022.9

  that its derivatives might have the potential to lead to novel anti-cancer agents based on anti-austerity strategy. The divergent synthesis of 4′-O-methylgrynullarin derivatives using the Suzuki-Miyaura coupling reaction as a key step and the evaluation of the synthesized derivatives revealed a clear structure-activity relationship. We found that the 6-prenyl moiety and 7-phenolic hydroxy group on the

  4'- O -Methylgrynullarin 1及其衍生物2-4在营养缺乏条件下表现出优先的细胞毒性，而在正常营养条件下没有细胞毒性，表明其衍生物可能具有产生基于抗紧缩性的新型抗癌剂的潜力战略。以 Suzuki-Miyaura 偶联反应为关键步骤的 4'- O -methylgrynullarin 衍生物的不同合成和对合成衍生物的评估揭示了明确的构效关系。我们发现异黄酮骨架上的 6-异戊二烯基部分和 7-酚羟基对于优先细胞毒性是必不可少的，即使C上的取代基-环比1-4更简单，一定程度上保持了细胞毒性。
• PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR LIGANDS AND PROCESS FOR PRODUCING THE SAME
  申请人：KANEKA CORPORATION

  公开号：EP1440688A1

  公开（公告）日：2004-07-28

  The present invention easily and efficiently provides a peroxisome proliferator-activated receptor ligand, and a composition for amelioration of insulin resistance or for prevention and/or amelioration of the insulin resistance syndrome containing the same, as an active ingredient. The present invention relates to a peroxisome proliferator-activated receptor ligand which comprises a prenylflavonoid, a chalcone derivative exclusive of prenylflavonoids, a flavonol derivative exclusive of prenylflavonoids, and a salt, a glycoside and/or an esterified substance thereof acceptable as a pharmaceutical preparation or a food or a beverage; a composition containing the above ligand; a plant-derived extract containing the above ligand; and a process for producing the above extract.

  本发明简便高效地提供了一种过氧化物酶体增殖体激活受体配体，以及一种用于改善胰岛素抵抗或预防和/或改善胰岛素抵抗综合征的组合物，其中含有该配体作为活性成分。 本发明涉及一种过氧化物酶体增殖体激活受体配体，它包括一种前黄酮类化合物、一种不包括前黄酮类化合物的查尔酮衍生物、一种不包括前黄酮类化合物的黄酮醇衍生物，以及可作为药物制剂或食品或饮料的盐、苷和/或酯化物质；一种含有上述配体的组合物；一种含有上述配体的植物提取物；以及一种生产上述提取物的工艺。
• Peroxisome proliferator activated receptor ligands and process for producing the same
  申请人：Mae Tatsumasa

  公开号：US20050014819A1

  公开（公告）日：2005-01-20

  The present invention easily and efficiently provides a peroxisome proliferator-activated receptor ligand, and a composition for amelioration of insulin resistance or for prevention and/or amelioration of the insulin resistance syndrome containing the same, as an active ingredient. The present invention relates to a peroxisome proliferator-activated receptor ligand which comprises a prenylflavonoid, a chalcone derivative exclusive of prenyl flavonoids, a flavonol derivative exclusive of prenylflavonoids, and a salt, a glycoside and/or an esterified substance thereof acceptable as a pharmaceutical preparation or a food or a beverage; a composition containing the above ligand; a plant-derived extract containing the above ligand; and a process for producing the above extract.

  本发明简便高效地提供了一种过氧化物酶体增殖体激活受体配体，以及一种用于改善胰岛素抵抗或预防和/或改善胰岛素抵抗综合征的组合物，其中含有该配体作为活性成分。本发明涉及一种过氧化物酶体增殖体激活受体配体，它包括一种前酰基类黄酮、一种不包括前酰基类黄酮的查尔酮衍生物、一种不包括前酰基类黄酮的黄酮醇衍生物，以及可作为药物制剂或食品或饮料的盐、苷和/或酯化物质；一种含有上述配体的组合物；一种含有上述配体的植物提取物；以及一种生产上述提取物的工艺。
• Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases
  作者：Kang Zhou、Xia Yu、Xiulan Xie、Shu-Ming Li

  DOI：10.1021/acs.jnatprod.5b00422

  日期：2015.9.25

  Flavonoids are found mainly in plants and exhibit diverse biological and pharmacological activities, which can often be enhanced by prenylations. In plants, such reactions are catalyzed by membrane-bound prenyltransferases. In this study, the prenylation of nine flavonoids from different classes by a soluble fungal prenyltransferase (AnaPT) involved in the biosynthesis of the prenylated indole alkaloid acetylaszonalenin is demonstrated. The behavior of AnaPT toward flavonoids regarding substrate acceptance and prenylation positions clearly differs from that of the indole prenyltransferase 7-DMATS. The two enzymes are therefore complementary in flavonoid prenylations.