15236-07-4Relevant articles and documents
Galangin 3-benzyl-5-methylether derivatives function as an adiponectin synthesis-promoting peroxisome proliferator-activated receptor γ partial agonist
Ko, Hyejin,Jang, Hongjun,An, Seungchan,Park, In Guk,Ahn, Sungjin,Gong, Junpyo,Hwang, Seok Young,Oh, Soyeon,Kwak, Soo Yeon,Choi, Won Jun,Kim, Hyoungsu,Noh, Minsoo
, (2021/12/20)
The upregulation of adiponectin production has been suggested as a novel strategy for the treatment of metabolic diseases. Galangin, a natural flavonoid, exhibited adiponectin synthesis-promoting activity during adipogenesis in human bone marrow mesenchymal stem cells. In target identification, galangin bound both peroxisome proliferator-activated receptor (PPAR) γ and estrogen receptor (ER) β. Novel galangin derivatives were synthesized to improve adiponectin synthesis-promoting compounds by increasing the PPARγ activity of galangin and reducing its ERβ activity, because PPARγ functions can be inhibited by ERβ. Three galangin 3-benzyl-5-methylether derivatives significantly promoted adiponectin production by 2.88-, 4.47-, and 2.76-fold, respectively, compared to the effect of galangin. The most potent compound, galangin 3-benzyl-5,7-dimethylether, selectively bound to PPARγ (Ki, 1.7 μM), whereas it did not bind to ERβ. Galangin 3-benzyl-5,7-dimethylether was identified as a PPARγ partial agonist in docking and pharmacological competition studies, suggesting that it may have diverse therapeutic potential in a variety of metabolic diseases.
New approach to flavonols via base-mediated cyclization: Total synthesis of 3,5,6,7-tetramethoxyflavone
Kraus, George A.,Gupta, Vinayak,Kempema, Aaron
, p. 385 - 388 (2012/03/10)
A new methodology for the synthesis of flavonols is described. The key step is a base-mediated cyclization-isomerization-elimination reaction which results in the formation of flavonols. Using this strategy, three flavonols are synthesized and characteriz
Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane
Compton, Benjamin J.,Larsen, Lesley,Weavers, Rex T.
experimental part, p. 718 - 726 (2011/03/19)
The reaction of 5,7-dimethoxyflavone with dimethyldioxirane (DMDO) gives the 2,3-epoxide rapidly at first. However, low levels of ring A hydroxylated by-products are also formed. With increasing proportions of DMDO, demethylation at C-5 becomes apparent and consumption of substrate is not matched by further significant build-up of the epoxide. Deactivation of ring A by the use of acyl groups removes this complication. 5,7-Diacylflavones give excellent yields of epoxides and monoacyl derivatives also react in good yield. Ionization potential maps derived from density functional theory calculations (B3LYP/6-31G), provide good visual indicators of the relative reactivity of the key nucleophilic loci. The epoxides may be isolated as such, or transformed into flavonols by treatment with p-toluenesulfonic acid.
3-O-Arylmethylgalangin, a novel isostere for anti-HCV 1,3-diketoacids (DKAs)
Lee, Hyo Seon,Park, Kwang-Su,Lee, Bokhui,Kim, Dong-Eun,Chong, Youhoon
experimental part, p. 7331 - 7337 (2010/11/20)
Through chelation of the metal ions at the enzyme active site, 1,3-diketoacids (DKAs) show potent inhibition of viral enzymes such as HIV integrase and HCV NS5B. In order to optimize the antiviral activity of the DKAs, structural modification of their metal-binding units, keto-enol acids or monoketo acids, have been actively performed. In this study, we proposed 3-O-arylmethylgalangin 3 as an alternative to ortho-substituted aromatic DKA, a potent inhibitor of HCV NS5B. As a proof-of-concept study, a series of 3-O-arylmethylgalangin derivatives (3a-3r) were prepared and their inhibitory activity against HCV NS5B was estimated. Structure-activity relationship of the 3-O-arylmethylgalangin derivatives was in good accordance with that of the ortho-substituted aromatic DKA series. In particular, two galangin ethers (3g and 3i) completely superimposable with the most potent ortho-substituted aromatic DKA analogue (2) in atom-by-atom fashion showed equipotent inhibitory activity to that of 2. Taken together, this result provides convincing evidence that the 3-O-arylmethylgalangin can successfully mimic the chelating function of the DKA pharmacophore to show potent inhibitory activity against the target enzyme, HCV NS5B.
Darzens reaction of 2-bromo-4,6-dimethoxy-3(2H)-benzofuranone with aromatic aldehydes to form flavonoids
Ottersbach, Philipp A.,Bolek, David,Lepicova, Eva,Nieger, Martin,Guetschow, Michael
, p. 1149 - 1153 (2008/12/21)
(Chemical Equation Presented) The applicability of 2-bromo-4,6-dimethoxy- 3(2H)-benzofuranone (1) to produce flavonoid-derived epoxides in the course of the Darzens reaction with aldehydes was investigated. However, instead of the epoxides, flavonols 3 and, in certain cases, benzofuranyl-substituted flavonols 4 were isolated. The generation of 3 is assumed due to a ring expansion of the initially formed epoxides. These flavonols can react with 1 to produce the unexpected 1:2 adducts 4 as minor products. The structure of the hexamethoxy derivative 4b (R1 = H, R2 = R3 = OMe) was confirmed by X-ray crystallographic analysis.
Synthesis of some commonly occurring 2-phenyl-4H-1-benzopyran-4-ones: Revised structures for three natural products
Parmar, Virinder S.,Gupta, Sandhya,Sinha, Rita,Sharma, Sunil K.
, p. 244 - 256 (2007/10/02)
5-Hydroxy-6,7-dimethoxyflavone, 5-hydroxy-7,8-dimethoxyflavone, 5-hydroxy-3,7-dimethoxyflavone, 3-hydroxy-5,7-dimethoxyflavone, 5-hydroxy-7,8-dimethoxyisoflavone and 5,7-dihydroxy-3-methoxyflavone and their derivatives have been synthesised to confirm the
Synthesis of Highly Functionalized Flavones and Chromones Using Cycloacylation Reactions and C-3 Functionalization. A Total Synthesis of Hormothamnione
McGarry, Lynda W.,Detty, Michael R.
, p. 4349 - 4356 (2007/10/02)
The cycloacylations of hydroxy- and methoxy-substituted phenols with aryl- and alkylpropiolic acids using Eaton's reagent (10percent phosphorus pentoxide in methanesulfonic acid) gives highly substituted flavones and chromones in up to 63 percent yield.Styrylchromones were prepared from 2-methylchromones by condensation reactions of the 2-methyl group with various substituted benzaldehydes in sodium ethoxide and ethanol in almost quantitative yield.Methylation or hydroxylation at C-3 of these highly substituted flavones and styrylchromones was accomplished in a highly regioselective manner employing lithium diisopropylamide followed by quenching with an electrophile.Quenching of the initial anion with methyl triflate gave 3-methyl products while quenching of the initial anion with trimethylborate followed by oxidation gave 3-hydroxy products.A total synthesis of the naturally occurring styrylchromone hormothamnione, containing a 3-methyl substituent, is reported by use of these synthetic techniques.
Regioselective synthesis of 2-arylidene coumaran-3-ones by dye-sensitized photooxygenation of 2-hydroxyphenyl-styrylketones in the presence of sodium dodecyl sulphate
Chawla, H. Mohindra,Sharma, S. Kumar
, p. 1611 - 1624 (2007/10/02)
2′-Hydroxyphenylstyrylketones when subjected to dye- sensitized photooxygenation in the presence of sodium dodecylsulphate (8x × 10-3M) in methanol, yielded the corresponding oxidatively cyclized products, i.e., 2-aryl idenecoumaran 3-ones and
