| 1621629-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1621629-24-0
• 化学式: C₁₉H₁₃BrO₃
• 分子量: 369.214
• InChiKey: VOHKRDHJROFQIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 硫酸 、 potassium hydroxide 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 0.25h， 生成 2-(3-bromophenyl)-4H-benzo[h]chromen-4-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
• 作为产物：
  描述：

  2-萘酚 在 吡啶 、 zinc(II) chloride 作用下， 反应 1.33h， 生成
  参考文献：
  名称：

  Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies

  摘要：

  A library of forty 7,8-benzoflavone derivatives was synthesized and evaluated for their inhibitory potential against cholesterol esterase (CEase). Among all the synthesized compounds seven benzoflavone derivatives (A-7, A-8, A-10, A-11, A-12, A-13, A-15) exhibited significant inhibition against CEase in in vitro enzymatic assay. Compound A-12 showed the most promising activity with IC50 value of 0.78 nM against cholesterol esterase. Enzyme kinetic studies carried out for A-12, revealed its mixed-type inhibition approach. Molecular protein ligand docking studies were also performed to figure out the key binding interactions of A-12 with the amino acid residues of the enzyme's active site. The A-12 fits well at the catalytic site and is stabilized by hydrophobic interactions. It completely blocks the catalytic assembly of CEase and prevents it to participate in ester hydrolysis mechanism. The favorable binding conformation of A-12 suggests its prevailing role as CEase inhibitor. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.01.020

文献信息

• Synthesis and evaluation of naphthoflavones as a new class of non purine xanthine oxidase inhibitors
  作者：Harbinder Singh、Sahil Sharma、Ritu Ojha、Manish K. Gupta、Kunal Nepali、P.M.S. Bedi

  DOI：10.1016/j.bmcl.2014.07.041

  日期：2014.9

  view of reported xanthine oxidase inhibitory potential of naphthopyrans and flavones, naphthoflavones as hybrids of the two were designed, synthesized and evaluated for in vitro xanthine oxidase inhibitory activity in the present study. The results of the assay revealed that the naphthoflavones possess promising inhibitory potential against the enzyme with IC50 values ranging from 0.62 to 41.2 μM.

  鉴于已报道了萘并吡喃类和黄酮类化合物的黄嘌呤氧化酶抑制潜力，在本研究中，设计，合成并评价了萘黄酮作为两者的杂合体的体外黄嘌呤氧化酶抑制活性。分析的结果表明，萘黄酮对酶具有抑制作用，IC 50值为0.62至41.2μM。结构活性关系表明，取代基的性质和位置在苯环的第二位显着影响其抑制活性。苯环的邻位和对位（第2位）上的卤素和硝基取代非常有利于活性。NF-4与p-氟苯环是最有效的抑制剂，IC 50值为0.62μM。还进行了酶动力学研究以研究其抑制机理，发现萘黄酮具有混合型抑制作用。通过分子模型研究合理化了NF-4对黄嘌呤氧化酶的显着抑制作用的基础。