2-p-tolyl-4H-benzo[h]chromen-4-one | 14756-26-4

• 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: 2-p-tolyl-4H-benzo[h]chromen-4-one
• 英文别名: 2-(4-methylphenyl)-4H-benzo[h]chromen-4-one；2-(4-methylphenyl)benzo[h]chromen-4-one
• CAS: 14756-26-4
• 化学式: C₂₀H₁₄O₂
• mdl: MFCD03994197
• 分子量: 286.33
• InChiKey: AVCQGCNOJZYRJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰基-1-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 2-p-tolyl-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

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。
• Application of α- and β-naphthoflavones as monooxygenase inhibitors of Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651 in transformation of 17α-methyltestosterone
  作者：Tomasz Janeczko、Jarosław Popłoński、Ewa Kozłowska、Monika Dymarska、Ewa Huszcza、Edyta Kostrzewa-Susłow

  DOI：10.1016/j.bioorg.2018.03.021

  日期：2018.8

  and 9% yields, respectively. S. racemosum KCh 105 afforded 7α-, 15α- and 11α-hydroxy derivatives with yields of 45%, 19% and 17%, respectively. Chaetomium sp. KCh 6651 afforded 15α-, 11α-, 7α-, 6β-, 9α-, 14α-hydroxy and 6β,14α-dihydroxy derivatives with yields of 31%, 20%, 16%, 7%, 5%, 7% and 4%, respectively. 14α-Hydroxy and 6β,14α-dihydroxy derivatives were determined as new compounds. Effect of various

  在这项工作中，芥蓝KCh 93，Syncephalastrum racemosum KCh 105和Chaetomium sp有效地羟基化了17α-甲基睾丸激素。KCH 6651. A.犁头KCH 93得到6β-，12β-，7α-，11α-，15α羟基衍生物与分别为44％，29％，6％，5％和9分％的收率。小号。总消旋体KCh 105提供7α-，15α-和11α-羟基衍生物，产率分别为45％，19％和17％。毛毛虫sp。KCh 6651提供15α-，11α-，7α-，6β-，9α-，14α-羟基和6β，14α-二羟基衍生物，产率分别为31％，20％，16％，7％，5％，7％和4 ％， 分别。确定了14α-羟基和6β，14α-二羟基衍生物为新化合物。测试了培养基中氮和碳的各种来源对生物转化的影响，但是没有影响底物转化的程度或形成的产物的组成。添加α-或β-萘黄酮抑制了17α-甲基睾丸酮的羟化作用，但没有改变所得产物的百分比组成。
• Benzoflavones as cholesterol esterase inhibitors: Synthesis, biological evaluation and docking studies
  作者：Harbinder Singh、Jatinder Vir Singh、Manish K. Gupta、Palwinder Singh、Sahil Sharma、Kunal Nepali、Preet Mohinder S. Bedi

  DOI：10.1016/j.bmcl.2017.01.020

  日期：2017.2

  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.
• 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.
• SYNERGISTIC DRUG COMBINATIONS PREDICTED FROM GENOMIC FEATURES AND SINGLE-AGENT RESPONSE PROFILES
  申请人：THE BROAD INSTITUTE, INC.

  公开号：US20210069230A1

  公开（公告）日：2021-03-11

  The present disclosure relates to discovery of specific synergistic drug combinations and mechanisms of drug resistance. Compositions involving newly-identified drug combinations as well as diagnostic and therapeutic methods related to such discoveries are provided.