4197-97-1Relevant articles and documents
Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents
Ramesh,Reddy, Ch. Sanjeeva,Suresh Babu,Reddy, P. Muralidhar,Srinivasa Rao,Parthasarathy
, p. 3696 - 3709 (2015)
A series of novel 2-amino 3-cyano 4-aryl pyrano[2,3H]chrysin derivatives (3a-m) were efficiently synthesized by one-pot three-component reaction of aromatic aldehydes, malononitrile and chrysin and characterized by 1H NMR, 13C NMR and mass spectral data. All the newly synthesized compounds were evaluated for their in vitro antimicrobial activity (antibacterial and antifungal). Among the tested compounds, 3a, 3g, 3h, 3j and 3k showed potent antibacterial activity compared to ciprofloxacin and the compounds 3a, 3g, 3h, 3i and 3k showed excellent antifungal activity compared to itrazole. The compounds 3a, 3g, 3h and 3k exhibited potent antimicrobial activity against all the selected pathogenic bacteria and fungi and emerged as potential molecules for further development. In addition, molecular modeling studies also performed to delineate the putative binding mode of these compounds. All of these chrysin derivatives (3a-m) obeyed the Lipinski's "rule of five" and have drug-likeness. Docking scores with appreciable binding energy values also exactly correlated with the experimental antimicrobial activity. The chemscore estimated by GOLD software was found to have a good correlation with the experimental inhibitory activity. Graphical Abstract: Docking of compound 3g with protein[Figure not available: see fulltext.] A series of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives (3a-m) has been synthesized and evaluated for their antimicrobial activity along with molecular modeling studies[Figure not available: see fulltext.]
Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
Hu, Chunling,Zhou, Zongbao,Xiang, Yuanhang,Song, Xiaoying,Wang, Hong,Tao, Kaiqi,Ye, Xiaochuan
, p. 194 - 205 (2018/04/19)
Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and showed various efficiency. Compounds D1–D30 showed no toxic effects on RAW 264.7 cells at the concentration 20 μM; among them, compounds D9, D13, and D19 exhibited best anti-inflammatory activity through decreasing IL-1β, IL-6, and TNF-α. Furthermore, their structure–activity relationships were discussed preliminarily.
Bioactive Formylated Flavonoids from Eugenia rigida: Isolation, Synthesis, and X-ray Crystallography
Zaki, Mohamed A.,Nanayakkara, N. P. Dhammika,Hetta, Mona H.,Jacob, Melissa R.,Khan, Shabana I.,Mohammed, Rabab,Ibrahim, Mohamed A.,Samoylenko, Volodymyr,Coleman, Christina,Fronczek, Frank R.,Ferreira, Daneel,Muhammad, Ilias
, p. 2341 - 2349 (2016/10/04)
Two new flavonoids, rac-6-formyl-5,7-dihydroxyflavanone (1) and 2′,6′-dihydroxy-4′-methoxy-3′-methylchalcone (2), together with five known derivatives, rac-8-formyl-5,7-dihydroxyflavanone (3), 4′,6′-dihydroxy-2′-methoxy-3′-methyldihydrochalcone (4), rac-7-hydroxy-5-methoxy-6-methylflavanone (5), 3′-formyl-2′,4′,6′-trihydroxy-5′-methyldihydrochalcone (6), and 3′-formyl-2′,4′,6′-trihydroxydihydrochalcone (7), were isolated from the leaves of Eugenia rigida. The individual (S)- and (R)-enantiomers of 1 and 3, together with the corresponding formylated flavones 8 (6-formyl-5,7-dihydroxyflavone) and 9 (8-formyl-5,7-dihydroxyflavone), as well as 2′,4′,6′-trihydroxychalcone (10), 3′-formyl-2′,4′,6′-trihydroxychalcone (11), and the corresponding 3′-formyl-2′,4′,6′-trihydroxydihydrochalcone (7) and 2′,4′,6′-trihydroxydihydrochalcone (12), were synthesized. The structures of the isolated and synthetic compounds were established via NMR, HRESIMS, and electronic circular dichroism data. In addition, the structures of 3, 5, and 8 were confirmed by single-crystal X-ray diffraction crystallography. The isolated and synthetic flavonoids were evaluated for their antimicrobial and cytotoxic activities against a panel of microorganisms and solid tumor cell lines.