3-(2-fluorophenyl)-1H-benzo[f]chromen-1-one | 652138-24-4

• 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: 3-(2-fluorophenyl)-1H-benzo[f]chromen-1-one
• 英文别名: UCCF 290；3-(2-Fluorophenyl)-1H-naphtho[2,1-b]pyran-1-one；3-(2-fluorophenyl)benzo[f]chromen-1-one
• CAS: 652138-24-4
• 化学式: C₁₉H₁₁FO₂
• 分子量: 290.294
• InChiKey: ZWMCNYORTGSOLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-乙酰基-2-萘酚 在 吡啶 、 硫酸 、 potassium hydroxide 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 1.25h， 生成 3-(2-fluorophenyl)-1H-benzo[f]chromen-1-one
  参考文献：
  名称：

  Benzoflavone derivatives as potent antihyperuricemic agents

  摘要：

  苯并黄酮衍生物经过合理设计、合成并针对黄嘌呤氧化酶进行评估，以检测它们的抗高尿酸作用，使用体外和体内方法。

  DOI：

  10.1039/c8md00512e

文献信息

• 5,6-Benzoflavones as cholesterol esterase inhibitors: synthesis, biological evaluation and docking studies
  作者：Jatinder V. Singh、Anumeet Kaur、Kavita Bhagat、Manish K. Gupta、Manwinder Singh、Harbinder Singh、Preet Mohinder S. Bedi

  DOI：10.1039/c7md00565b

  日期：——

  with an IC50 value of 0.73 nM against cholesterol esterase. To determine the type of inhibition, enzyme kinetic studies were carried out for B-16, which revealed its mixed-type inhibition approach. Moreover, to figure out the key binding interactions of B-16 with the amino acid residues of the enzyme's active site, molecular protein–ligand docking studies were also performed. B-16 completely blocks the

  在继续努力开发有效的胆固醇酯酶（CEase）抑制剂时，通过改变先前报道的7,8-苯并黄酮中与黄酮骨架相连的苯环的位置，合理设计和合成了一系列5,6-苯并黄酮衍生物。使用分光光度测定法检查所有合成的化合物对胆固醇酯酶（CEase）的抑制潜力。在这四十种化合物中，在体外酶促测定中，七种衍生物（B - 10至B - 16）对CEase的抑制率超过90％。化合物B - 16的IC 50表现出最有希望的活性胆固醇酯酶的值为0.73 nM。为了确定抑制的类型，对B - 16进行了酶动力学研究，揭示了其混合类型的抑制方法。此外，为了弄清B - 16与酶活性位点氨基酸残基的关键结合相互作用，还进行了分子蛋白质-配体对接研究。B - 16完全阻断了CEase的催化组装，并阻止了它参与酯的水解机理。B - 16的良好结合构象表明其作为CEase抑制剂的主要作用。总体而言，研究表明，顺式环A相对于环C的羰基的取
• Benzoflavone activators of the cystic fibrosis transmembrane conductance regulator: towards a pharmacophore model for the nucleotide-binding domain
  作者：Mark F Springsteel、Luis J.V Galietta、Tonghui Ma、Kolbot By、Gideon O Berger、Hong Yang、Christopher W Dicus、Wonken Choung、Chao Quan、Anang A Shelat、R.Kiplin Guy、A.S Verkman、Mark J Kurth、Michael H Nantz

  DOI：10.1016/s0968-0896(03)00435-8

  日期：2003.9

  using cell-based assays, of a series of benzoflavone analogues to examine structure-activity relationships and to identify compounds having greater potency for activation of both wild type CFTR and a mutant CFTR (G551D-CFTR) that causes cystic fibrosis in some human subjects. Using UCCF-029 as a structural guide, a panel of 77 flavonoid analogues was prepared. Analysis of the panel in FRT cells indicated

  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
• β-Naphthoflavone analogs as potent and soluble aryl hydrocarbon receptor agonists: Improvement of solubility by disruption of molecular planarity
  作者：Yuji Fujita、Mitsuhiro Yonehara、Masashi Tetsuhashi、Tomomi Noguchi-Yachide、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1016/j.bmc.2009.12.036

  日期：2010.2

  The physiological role of aryl hydrocarbon receptor (AhR) is not yet fully understood, and investigation is hampered by the limited solubility of reported AhR ligands in aqueous media. To achieve improved solubility, we focused on our previous finding that planarity-disruption of molecules leads to less efficient crystal packing and greater aqueous solubility. Here, we describe chemical modification of an AhR agonist, beta-naphthoflavone, focusing on planarity-disruption. As expected, introduction of substituents at the ortho-positions of the phenyl group resulted in greater solubility. Among the compounds prepared, the fluoro analog showed more potent AhR agonistic activity and greater solubility than did b-naphthoflavone. Our results indicate that this strategy to improve aqueous solubility, that is, introduction of substituent(s) that disrupt planarity, may be generally applicable to bicyclic molecules. (C) 2010 Elsevier Ltd. All rights reserved.
• Benzoflavone derivatives as potent antihyperuricemic agents
  作者：Jatinder V. Singh、Gurbachan Mal、Gurleen Kaur、Manish K. Gupta、Amritpal Singh、Kunal Nepali、Harbinder Singh、Sahil Sharma、Preet Mohinder S. Bedi

  DOI：10.1039/c8md00512e

  日期：——

  Benzoflavone derivatives were rationally designed, synthesized and evaluated against the xanthine oxidase enzyme to check their antihyperuricemic effect by using in vitro as well as in vivo methods.

  苯并黄酮衍生物经过合理设计、合成并针对黄嘌呤氧化酶进行评估，以检测它们的抗高尿酸作用，使用体外和体内方法。