19725-47-4Relevant articles and documents
Methoxyflavone inhibitors of cytochrome P450
McKendall, Michael,Smith, Tasha,Anh, Kien,Ellis, Jamie,McGee, Terri,Foroozesh, Maryam,Zhu, Naijue,Stevens, Cheryl L. Klein
, p. 231 - 237 (2008)
Cytochrome P450 enzymes are a superfamily of enzymes involved in the metabolism of endogenous compounds as well as xenobiotics. Due to the large number of reactions catalyzed by these enzymes and their importance in drug metabolism and carcinogenesis, they have been the focus of many studies over the years. Based on the knowledge that flavones are natural substrates of certain P450 enzymes (such as P450 1A2) involved in carcinogenesis, we have synthesized and studied a number of flavonoids as potential inhibitors of these enzymes. These compounds are structurally very similar to the natural flavone substrates of these enzymes but have methoxy substituents at various positions. Here we are reporting the synthesis, structural analysis, X-ray crystal structures, and preliminary inhibition studies of four methoxyflavones from this series. Crystallographic data: 2′-methoxyflavone, P-1, a = 7.2994(8) A, b = 8.3322(7) A, c = 10.8240(10) A, α = 97.905(8)°, β = 92.779(10)°, γ = 111.105(8)°, V = 604.9(1) A3; 3′-methoxyflavone, P21/n, a = 15.1313(16) A, b = 3.9699(4) A, c = 19.9454(16) A, β = 91.673(8)°, V = 1197.6(2) A3; 4′-methoxyflavone, P21/n, a = 16.451(12) A, b = 3.881(1) A, c = 19.529(16) A, β = 106.65(1)°, V = 1195.1(4) A3; 3′,4′- dimethoxyflavone, C2/c, a = 30.819(5) A, b = 4.0857(7) A, c = 26.100(3) A, β = 124.21(1)°, V = 2717.6(7) A3. Methoxyflavone Inhibitors of Cytochrome P450 Michael McKendall, Tasha Smith, Kien Anh, Jamie Ellis, Terri McGee, Maryam Foroozesh, Naijue Zhu and Cheryl L. Klein Stevens *This paper is a report of the synthesis, structural analysis, X-ray crystal structures, and preliminary inhibition studies of 2′-methoxyflavone, 3′-methoxyflavone, 4′-methoxyflavone, and 3′,4′-dimethoxyflavone. [Figure not available: see fulltext.]
OXYTHALLATION OF FLAVENES.I;DIRECT CONVERSION OF FLAVENES TO FLAVONES WITH THALLIUM(III) NITRATE.
Hatam, N. A. R.,Nacy, W. G.
, p. 4455 - 4456 (1983)
Oxythallation of flav-2-enes and flav-3-enes with 2 moles equivalent of TTN in methanol gives flavones.
Efficient synthesis of frutinone A and its derivatives through palladium-catalyzed C-H activation/carbonylation
Shin, Yongje,Yoo, Changho,Moon, Youngtaek,Lee, Yunho,Hong, Sungwoo
, p. 878 - 881 (2015)
Frutinone A, a biologically active ingredient of an antimicrobial herbal extract, demonstrates potent inhibitory activity towards the CYP1A2 enzyme. A three-step total synthesis of frutinone A with an overall yield of 44 is presented. The construction of
Synthesis and solid state self-assembly of a 1,4-diazepine derivative: Water cluster as molecular glue and conformational isomerism
Zia, Mehwash,Khalid, Muhammad,Hameed, Shahid,Irran, Elisabeth,Naseer, Muhammad Moazzam
, (2020)
Diazepine (a seven membered heterocycle) derivatives have emerged as “privileged structures” in chemical biology and medicinal chemistry. In this article, synthesis of a 1, 4-diazepine derivative 4 from flavone 3 in excellent yield is described. The solid state self-assembly pertaining to diazepine derivative 4 was investigated with X-ray crystallography. Fascinatingly, the solid state structure of 4 represents a remarkable example of water cluster acting as structural glue to instigate conformational isomerism and hence facilitate the crystallization process by compensating the imbalance of hydrogen-bond donors and acceptors. NBO and QTAIM based calculations show that the hydrogen-bonding network of water molecules and hyper conjugative interactions play a vital role for stabilization of structure in the solid state. To our knowledge, presented here is the first illustration of any solvent cluster stabilizing the solid-state structure in a diazepine family. In addition, the crystal structure of flavone 3 hitherto not reported is also reported.
CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones
Sun, Dong-Wei,Zhou, Yong-Yan,Jiang, Min,Nian, Tang,Liu, Jin-Tao
, (2021/05/31)
An efficient intramolecular cyclization reaction of β-diketones containing a phenyl group with an ortho-hydroxyl substituent was achieved. Using CF3SOCl as an additive, the reaction took place under transition-metal-free and mild conditions. A series of flavones were synthesized in moderate to excellent yields.
Long-afterglow light-storing type organic light-emitting material and preparation method thereof
-
, (2021/02/13)
The invention relates to the technical field of organic synthesis, particularly to a long-afterglow light-storing type organic light-emitting material and a preparation method thereof, and discloses apreparation method of a long-afterglow light-storing type organic light-emitting material with a structure as shown in a formula (I). According to the invention, the preparation method is cheap and easily-available in reaction raw materials, low in preparation cost, simple to operate, novel in reaction route, short in reaction time and synthetic route, mild in reaction condition, clean in reaction system and high in safety, and can obtain the long-afterglow light-storing type organic light-emitting material with the structure shown in the formula (I) with extremely high yield and selectivity;according to the preparation method, violent high-temperature conditions are avoided, highly toxic reagents and expensive metal catalysts are not used, and the preparation method is green and economical; and the preparation method has the advantages of simple post-treatment mode and less purification loss, greatly saves manpower, material resources and time, and can adapt to and meet the requirements of industrial production.
Rh-Catalyzed aldehydic C-H alkynylation and annulation
Ramakrishna, Boddu S.,Rao, Maddali L. N.
, p. 1402 - 1411 (2020/03/03)
Novel Rh-catalyzed aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-
Design, synthesis and biological evaluation of substituted flavones and aurones as potential anti-influenza agents
Chintakrindi, Anand S.,Gohil, Devanshi J.,Chowdhary, Abhay S.,Kanyalkar, Meena A.
supporting information, (2019/11/29)
We designed a series of substituted flavones and aurones as non-competitive H1N1 neuraminidase (NA) inhibitors and anti-influenza agents. The molecular docking studies showed that the designed flavones and aurones occupied 150-cavity and 430-cavity of H1N1-NA. We then synthesized these compounds and evaluated these for cytotoxicity, reduction in H1N1 virus yield, H1N1-NA inhibition and kinetics of inhibition. The virus yield reduction assay and H1N1-NA inhibition assay demonstrated that the compound 1f (4-methoxyflavone) had the lowest EC50 of 9.36 nM and IC50 of 8.74 μM respectively. Moreover, kinetic studies illustrated that compounds 1f and 2f had non-competitive inhibition mechanism.
Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides
Cheng, Kang,Chen, Jinkang,Jin, Licheng,Zhou, Jian,Jiang, Xinpeng,Yu, Chuanming
, p. 392 - 398 (2019/09/03)
Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.
Temperature-Controlled Stereodivergent Synthesis of 2,2′-Biflavanones Promoted by Samarium Diiodide
Soto, Martín,Soengas, Raquel G.,Silva, Artur M. S.,Gotor-Fernández, Vicente,Rodríguez-Solla, Humberto
, p. 13104 - 13108 (2019/10/21)
In this work, the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2′-biflavanones promoted by samarium diiodide is reported. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2′-biflavanones bearing different substitution patterns at the aromatic ring in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2′-biflavanones and the selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single-crystal X-ray diffraction experiments.
