4'-Hydroxy-beta-naphthoflavone | 98166-72-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4'-Hydroxy-beta-naphthoflavone
• 英文别名: 4’-hydroxy-β-naphthoflavone；4'-hydroxy-β-naphthoflavone；3-(4-hydroxy-phenyl)-benzo[f]chromen-1-one；3-(4-Hydroxy-phenyl)-benzo[f]chromen-1-on；4'-HYDROXY-b-NAPHTHOFLAVONE；3-(4-hydroxyphenyl)benzo[f]chromen-1-one
• CAS: 98166-72-4
• 化学式: C₁₉H₁₂O₃
• 分子量: 288.302
• InChiKey: AUDZFDILQOXUBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-Hydroxy-beta-naphthoflavone 在 2,2,6,6-tetramethyl-piperidine-N-oxyl [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 乙腈 为溶剂， 以16%的产率得到3-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-1H-benzo[f]chromen-1-one
  参考文献：
  名称：

  首次合成原芹菜酮及其类似物作为有效的细胞毒性剂。

  摘要：

  从火假单胞菌分离的原芹菜酮（1）以前对五种人类癌细胞系显示出显着的细胞毒活性。在持续的结构-活性关系研究中，实现了1的第一个全合成和修饰。评价所有合成的化合物和相关中间体对五种人类癌细胞系HepG2，Hep3B，MDA-MB-231，MCF-7和A549的细胞毒活性。其中24个细胞毒性比1个高2.2-14.2倍，萘基A环类似物显着增强了其活性。

  DOI：

  10.1021/jm070363a
• 作为产物：
  描述：

  1-乙酰基-2-萘酚 在 sodium hydroxide 、 五氯化磷 、 氢碘酸 、 乙酸酐 、 溶剂黄146 、 苯 作用下， 生成 4'-Hydroxy-beta-naphthoflavone
  参考文献：
  名称：

  CCCLXI：色酮组中的合成实验。第四部分1：4-βα-萘并吡喃酮

  摘要：

  DOI：

  10.1039/jr9310002591

文献信息

• COMPOSITION FOR TREATING CANCER CELLS AND SYNTHETIC METHOD FOR THE SAME
  申请人：Wu Yang-Chang

  公开号：US20090054516A1

  公开（公告）日：2009-02-26

  A pharmaceutical composition having a cytotoxic effect to a cancer cell and a method for the same are provided. The pharmaceutical composition comprises a flavonoid compound having at least one of the following formulas: wherein B ring is a 4-oxo-cyclohexa-2,5-dienyl group, and any one of R 1 -R 12 is one selected from a group consisting of hydrogen group, hydroxyl group, C1-C20 alkyl group, C1-C20 ether group, C1-C20 ester group, carboxyl group, halogen and sugar.

  提供一种对癌细胞具有细胞毒作用的药物组合物及其方法。所述药物组合物包括至少具有以下一种结构的黄酮类化合物： 其中B环是4-氧代环己-2,5-二烯基基团，R1-R12中的任一是从氢基团、羟基团、C1-C20烷基团、C1-C20醚基团、C1-C20酯基团、羧基团、卤素和糖组成的群体中选择的一种。
• Synthesis and SAR Study of Anticancer Protoflavone Derivatives: Investigation of Cytotoxicity and Interaction with ABCB1 and ABCG2 Multidrug Efflux Transporters
  作者：Balázs Dankó、Szilárd Tóth、Ana Martins、Máté Vágvölgyi、Norbert Kúsz、Joseph Molnár、Fang-Rong Chang、Yang-Chang Wu、Gergely Szakács、Attila Hunyadi

  DOI：10.1002/cmdc.201700225

  日期：2017.6.7

  recently showed that protoflavones display activity in MDR cancer cell lines that overexpress the P-glycoprotein (P-gp) drug efflux pump. In this study, 52 protoflavones, including 22 new derivatives, were synthesized and tested against a panel of drug-sensitive parental cells and their MDR derivatives obtained by transfection with the human ABCB1 or ABCG2 genes, or by adaptation to chemotherapeutics

  持续需要针对多药耐药性（MDR）癌症的新疗法。天然化合物是新型抗癌药的有希望的来源。我们最近表明，原黄酮在过度表达P-糖蛋白（P-gp）药物外排泵的MDR癌细胞系中显示活性。在这项研究中，合成了52种原黄酮，其中包括22种新衍生物，并针对一组药物敏感的亲代细胞及其通过用人ABCB1或ABCG2基因转染或通过适应化学疗法获得的MDR衍生物进行了测试。除了被确定为弱ABCG2底物的原芹菜酮外，所有原黄酮均绕过了这两个转运蛋白赋予的抗性。发现大多数化合物对MCF-7Dox和KB-V1细胞系具有中等至强（高达13倍）的选择性，但不适用于经过工程改造以过表达MDR转运蛋白的MDR细胞。我们的结果表明，原黄酮可以通过逃避P-gp介导的外排而克服MDR癌症。
• Naphthoflavone propargyl ether inhibitors of cytochrome P450
  作者：Naijue Zhu、Danielle Lightsey、Maryam Foroozesh、William Alworth、Amit Chaudhary、Kristine L. Willett、Cheryl L. Klein Stevens

  DOI：10.1007/s10870-005-9061-5

  日期：2006.5

  Cytochrome P450 enzymes protect the body from foreign substances through a mechanism that involves oxidation of those substances into more readily excretable polar compounds. It has been shown that some naphthoflavones function as substrates of certain P450 enzymes (CYP1A1 and CYP1B1) and with appropriate structural changes may become inhibitors. Moreover, propargyl ether derivatives of adamantane have been shown to function as selective inactivators of some P450 enzymes (CYP2B1 and CYP2B5). In an attempt to improve the potency and selectivity of inhibition, we have designed and synthesized a series of naphthoflavone propargyl ethers. We report here the synthesis, X-ray crystal structures, and inhibition data (IC50 of EROD inhibition in CYP1A1 and CYP1B1 enzymes) of α-naphthoflavone 2′-propargyl ether, β-naphthoflavone 2′-propargyl ether, α-naphthoflavone 4′-propargyl ether, and β-naphthoflavone 4′-propargyl ether. Crystallographic data: α-naphthoflavone 2′-propargyl ether, $$P\bar 1$$ , a=7.775(1) Å, b=8.062(1) Å, c=13.110(1) Å, α=84.32(1)°, β=75.42(1)°, γ=86.56(1)°, V=790.8(2) Å3; β-naphthoflavone 2′-propargyl ether, $$P\bar 1$$ , a=7.605(2) Å, b=7.793(1) Å, c=14.167(2) Å, α=77.06(1)°, β=75.41(1)°, γ=89.54(1)°, V=790.9(2) Å3; α-naphthoflavone 4′-propargyl ether, P21/n, a=14.595(2) Å, b=4.708(1) Å, c=24.745(6) Å, β=106.31(2)°, V=1631.8(7) Å3; β-naphthoflavone 4′-propargyl ether, P1, a=4.8871(5) Å, b= 7.9597(7) Å, c=21.788(3) Å, α=81.771(9)°, β=89.918(10)°, γ=72.223(8)°, V= 797.9(2) Å3.

  细胞色素P450酶通过将外来物质氧化成更易于排泄的极性化合物，从而保护身体免受这些物质的伤害。已有研究表明，某些萘黄酮可以作为特定P450酶（CYP1A1和CYP1B1）的底物，并且在适当结构改变后可能成为抑制剂。此外，金刚烷的炔丙基醚衍生物已被证明可以作为某些P450酶（CYP2B1和CYP2B5）的选择性灭活剂。为了提高抑制作用的效力和选择性，我们设计和合成了一系列萘黄酮炔丙基醚。在此，我们报告了α-萘黄酮2′-炔丙基醚、β-萘黄酮2′-炔丙基醚、α-萘黄酮4′-炔丙基醚和β-萘黄酮4′-炔丙基醚的合成、X射线晶体结构和抑制数据（CYP1A1和CYP1B1酶中EROD抑制的IC50值）。结晶学数据：α-萘黄酮2′-炔丙基醚，$$P\bar 1$$，a=7.775(1) Å，b=8.062(1) Å，c=13.110(1) Å，α=84.32(1)°，β=75.42(1)°，γ=86.56(1)°，V=790.8(2) Å3；β-萘黄酮2′-炔丙基醚，$$P\bar 1$$，a=7.605(2) Å，b=7.793(1) Å，c=14.167(2) Å，α=77.06(1)°，β=75.41(1)°，γ=89.54(1)°，V=790.9(2) Å3；α-萘黄酮4′-炔丙基醚，P21/n，a=14.595(2) Å，b=4.708(1) Å，c=24.745(6) Å，β=106.31(2)°，V=1631.8(7) Å3；β-萘黄酮4′-炔丙基醚，P1，a=4.8871(5) Å，b=7.9597(7) Å，c=21.788(3) Å，α=81.771(9)°，β=89.918(10)°，γ=72.223(8)°，V=797.9(2) Å3。
• Composition for treating cancer cells and synthetic method for the same
  申请人：Kaohsiung Medical University

  公开号：EP1980248A1

  公开（公告）日：2008-10-15

  A pharmaceutical composition having a cytotoxic effect to a cancer cell and a method for the same are provided. The pharmaceutical composition comprises a flavonoid compound having at least one of the following formulas: and wherein B ring is a 4-oxo-cyclohexa-2,5-dienyl group, and any one of R1-R12 is one selected from a group consisting of hydrogen group, hydroxyl group, C1-C20 alkyl group, C1-C20 ether group, C1-C20 ester group, carboxyl group, halogen and sugar.

  本发明提供了一种对癌细胞具有细胞毒性作用的药物组合物及其制备方法。该药物组合物包含一种黄酮类化合物，其至少具有以下一种分子式： 和 其中B环是4-氧代-环己-2,5-二烯基，R1-R12中的任何一个选自氢基、羟基、C1-C20烷基、C1-C20醚基、C1-C20酯基、羧基、卤素和糖组成的组。
• Fungal metabolism of naphthoflavones
  作者：Jarosław Popłoński、Sandra Sordon、Tomasz Tronina、Agnieszka Bartmańska、Ewa Huszcza

  DOI：10.1016/j.molcatb.2015.04.007

  日期：2015.7

  Naphthoflavones (benzoflavones) are synthetic flavonoids commonly used in drug metabolism studies as selective activators or inhibitors of cytochrome P-450 enzymes. Nowadays they are also used as a component of food supplements for body builders. There is no data regarding naphthoflavone microbial metabolism. In the present studies sixty-three fungal strains have been screened for their ability to transform alpha-naphthoflavone (7,8-benzoflavone) or beta-naphthoflavone (5,6-benzoflavone). Five strains belonging to the genera Penicillium, Cladosporium, Aspergillus and Verticillium transformed alpha-naphthoflavone and beta-naphthoflavone to the corresponding 4'-hydroxy derivatives. These selected fungi have been used in a further study on biotransformation of naphthoflavones with a differently substituted B-ring. Only 4'-methoxy derivatives have been transformed to the related 4'-hydroxy products. Selected strains are good biocatalysts to obtain 4'-hydroxy naphthoflavones in the one step reaction. (C) 2015 Elsevier B.V. All rights reserved.