萘黄酮 | 6051-88-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 萘黄酮
• 英文名称: 2-phenyl-4H-benzo[g]chromen-4-one
• 英文别名: α-naphtho-flavone；α-naphthoflavone；γ-naphthoflavone；UCCF-304；2-phenyl-benzo[g]chromen-4-one；2-Phenyl-benzo[g]chromen-4-on；4H-Naphtho(2,3-b)pyran-4-one, 2-phenyl-；2-phenylbenzo[g]chromen-4-one
• CAS: 6051-88-3
• 化学式: C₁₉H₁₂O₂
• 分子量: 272.303
• InChiKey: KUHLNOSGIHMGFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914399090

反应信息

• 作为反应物：
  描述：

  萘黄酮 在 NADPH-450 reductase 、 rat liver epoxide hydrolase 、 recombinant human cytochrome P₄₅₀ 1A₁ expressed in E_. coli 作用下， 以 水 为溶剂， 反应 0.17h， 生成 α-naphthoflavone-5,6-dihydrodiol
  参考文献：
  名称：

  Oxidation of Benzo[a]pyrene by Recombinant Human Cytochrome P450 Enzymes

  摘要：

  The oxidation of benzo[a]pyrene (B[a]P) was examined using reconstituted systems prepared with recombinant human cytochrome P450 (P450) enzymes 1A1, 1A2, 2C8, 2C10, 2E1, and 3A4 and with microsomes prepared from Saccharomyces cerevisiae expressing recombinant human P450s 2C8, 2C9, and 2C18. Products measured by HPLC included the 3- and 9-phenols, the 4,5-, 7,8-, and 9,10-dihydrodiols (detected in the presence of epoxide hydrolase), and products in the polar fraction eluting immediately after the void volume. The most active enzyme in all reactions was P450 1A1. P450 3A4 and P450 1A2 formed appreciable amounts of several of the products, including the 3-phenol. P450 2C enzymes and P450 2E1 formed relatively low amounts of all B[a]P products. Consideration of these patterns along with knowledge of levels of expression of the P450s in human tissues and previous results with microsomes leads to the conclusion that P450 1A1 should dominate the oxidation of B[a]P in tissues where it is present and inducible. In human liver the level of P450 1A1 is low and P450 3A4, P450 2C subfamily enzymes, and P450 1A2 probably all contribute. Of the human P450s considered here, P450 1A2 was the most active hepatic enzyme forming the 7,8-dihydrodiol. 7,8-Benzoflavone stimulated the oxidation of B[a]P by P450 3A4 and inhibited the oxidations catalyzed by P450 1A2. The extent of inhibition of P450 1A1 was less (than with P450 1A2), probably due to the rapid oxidation of 7,8-benzoflavone by P450 1A1. The major 7,8-benzoflavone product appears to be the 5,6-oxide.

  DOI：

  10.1021/tx00043a018
• 作为产物：
  描述：

  1-(3-羟基萘-2-基)乙酮 在 吡啶 、 氢氧化钾 、 硫酸 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 生成 萘黄酮
  参考文献：
  名称：

  囊性纤维化跨膜电导调节剂的苯酮黄酮激活剂：针对核苷酸结合域的药效团模型。

  摘要：

  我们以前对黄酮类化合物和相关杂环的筛选具有激活囊性纤维化跨膜电导调节剂（CFTR）氯化物通道的能力，这表明UCCF-029是一种7,8-苯并黄酮，是一种有效的活化剂。在本研究中，我们描述了使用基于细胞的分析方法对一系列苯并黄酮类似物进行合成和评估，以检查其结构活性关系，并鉴定出对野生型CFTR和突变型CFTR（G551D -CFTR）在某些人类受试者中引起囊性纤维化。使用UCCF-029作为结构指导，制备了77种类黄酮类似物。对FRT细胞中面板的分析表明，黄酮A环在7,8位的苯环显着提高了化合物活性和几种类黄酮的效力。在3或4位上引入B环吡啶基氮也可提高CFTR活性，但这种结构修饰的影响不如苯甲环化均匀。最有效的新类似物UCCF-339以1.7 microM的K（d）激活了野生型CFTR，它比以前最有效的CFTR类黄酮活化剂芹菜素具有更高的活性。苯并黄酮类化合物中的几种化合物也可以活化G5

  DOI：

  10.1016/s0968-0896(03)00435-8

文献信息

• Synthesis of 4<i>H</i>-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes
  作者：Yixia Yue、Jinsong Peng、Deqiang Wang、Yunyun Bian、Peng Sun、Chunxia Chen

  DOI：10.1021/acs.joc.7b00640

  日期：2017.5.19

  The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.

  开发了钯催化的烯基溴和醛的分子内酰化反应，以有效合成4 H -chromen-4-ones。以Pd（PPh 3）4 / Xphos为催化剂，以K 2 CO 3为碱，该方案被用于合成少量的，功能多样的黄酮类化合物，在1,4-二恶烷中的产率为中等。
• Metal-free, visible-light-induced C(sp2)-H functionalization/C O bond formation for the synthesis of flavones using air as an oxidant
  作者：Yuntao Bai、Manqiang Yang、Shao-Xia Lin、Rahul Anil Borse、Mahesh Bhagwan Thoke、Daqiang Yuan

  DOI：10.1016/j.tetlet.2023.154481

  日期：2023.5

  A green and practical method for synthesizing high value-added flavones from readily available chalcones based on visible-light-induced C(sp2)-H functionalization /CO bond formation is described. This reaction utilizes organic dye (Rose Bengal) as the photosensitizer and atmospheric oxygen as the green oxidant and oxygen source without any metals and external additive requirement. Through this methodology

  描述了一种基于可见光诱导的 C(sp 2 )-H 功能化/C O 键形成，从现成的查耳酮合成高附加值黄酮的绿色实用方法。该反应以有机染料（玫瑰红）为光敏剂，大气中的氧气为绿色氧化剂和氧源，无需任何金属和外加剂。通过这种方法，以中等到良好的收率合成了多种黄酮。
• Nowlan et al., Journal of the Chemical Society, 1950, p. 340,342
  作者：Nowlan et al.

  DOI：——

  日期：——
• Dunne et al., Journal of the Chemical Society, 1950, p. 1252,1257
  作者：Dunne et al.

  DOI：——

  日期：——
• 344. Chromones of the naphthalene series. Part I. Transformation of o-aroyloxyacetoarones into o-hydroxydiaroylmethanes
  作者：V. V. Virkar、T. S. Wheeler

  DOI：10.1039/jr9390001679

  日期：——