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• 67139-34-8 Methanesulfonic acid (2R,3R)-2-(4-nitro-phenyl)-4-oxo-chroman-3-yl ester 
• 118-93-4 o-hydroxyacetophenone 
• 555-16-8 4-nitrobenzaldehdye 
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• 241128-50-7 Cu(PPh₃)2(4'-nitroflavonolate) 

Relevant academic research and scientific papers

Exploring 3-Benzyloxyflavones as new lead cholinesterase inhibitors: synthesis, structure–activity relationship and molecular modelling simulations

In this protocol, a series of 3-benzyloxyflavone derivatives have been designed, synthesized, characterized and investigated in?vitro as cholinesterase inhibitors. The findings showed that all the synthesized target compounds (1–10) are potent dual inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes with varying IC50 values. In comparison, they are more active against AChE than BChE. Remarkably, amongst the series, the compound 2 was identified as the most active inhibitor of both AChE (IC50 = 0.05 ± 0.01 μM) and BChE (IC50 = 0.09 ± 0.02 μM) relative to the standard Donepezil (IC50 = 0.09 ± 0.01 for AChE and 0.13 ± 0.04 μM for BChE). Moreover, the derivatives 5 (IC50 = 0.07 ± 0.02 μM) and 10 (0.08 ± 0.02 μM) exhibited the highest selective inhibition against AChE as compared to the standard. Preliminary structure-activity relationship was established and thus found that cholinesterase inhibitory activities of these compounds are highly dependent on the nature and position of various substituents on Ring-B of the 3-Benzyloxyflavone scaffolds. In order to find out the nature of binding interactions of the compounds and active sites of the enzymes, molecular docking studies were carried out. (Figure presented.) HIGHLIGHTS 3-benzyloxyflavone analogues were designed, synthesized and characterized. The target molecules (1–10) were evaluated for their inhibitory potential against AChE and BChE inhibitory activities. Limited structure-activity relationship was developed based on the different substituent patterns on aryl part. Molecular docking studies were conducted to correlate the in?vitro results and to identify possible mode of interactions at the active pocket site of the enzyme. Communicated by Ramaswamy H. Sarma.

Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened for in?vitro against mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis, 1H-, 13C-NMR) and mass spectrometry (EI-MS). The structure of compound 15 was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibiotics i.e. Cefixime and Clotrimazole. Amongst the series, the compounds 2, 4, 5, 6, 7, 10, 11, 14 and 22 exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound 2 (IC50 = 0.280 ± 0.010 μg/ml) was found almost sixfold and derivative 5 (IC50 = 0.230 ± 0.020 μg/ml) about sevenfold more active as compared to standard Kojic acid (IC50 =1.79 ± 0.6 μg/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma.

Synthesis, characterization and biological evaluation of ruthenium flavanol complexes against breast cancer

Four Ru(II) DMSO complexes (M1R-M4R) having substituted flavones viz. 3-Hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one (HL1), 3-Hydroxy-2-(4-nitrophenyl)-4H-chromen-4-one (HL2), 3-Hydroxy-2-(4-dimethylaminophenyl)-4H–chromen-4-one (HL3) and 3-Hydroxy-2-(4-chlorophenyl)-4H-chromen-4-one (HL4) were synthesized and characterized by elemental analysis, IR, UV–Vis, 1H NMR spectroscopies and ESI-MS. The molecular structures of the complexes were investigated by integrated spectroscopic and computational techniques (DFT). Both ligands as well as their complexes were screened for anticancer activities against breast cancer cell lines MCF-7. Cytotoxicity was assayed by MTT [3-(4, 5-dimethyl thiazol-2-yl)-2, 5-diphenyl tetrazolium bromide] assay. All ligands and their complexes exhibited significant cytotoxic potential of 5–40?μM concentration at incubation period of 24?h. The cell cytotoxicity increased significantly in a concentration-dependent manner. In this series of compounds, HL2 (IC50 17.2?μM) and its complex M2R (IC50 16?μM) induced the highest cytotoxicity.

An expeditious synthesis of flavonols promoted by montmorillonite KSF clay and assisted by microwave irradiation under solvent-free conditions

A simple, efficient, rapid, and ecofriendly synthesis of flavonols in >90% yield from 2′-(mesyloxy)epoxychalcones (=2-(3-aryl-2,3- epoxypropanoyl)phenyl methanesulfonates) promoted by montmorillonite KSF clay and assisted by microwave irradiation has been described. Copyright

Flavonoids. 43. Deprotonation-initiated Aryl Migration with Sulfur Dioxide Extrusion: A Route to 2,3-Dihydro-2,3-diaryl-3-hydroxy-4H-1-benzopyran-4-ones

Treatment of trans-2,3-dihydro-2-aryl-3-nosyloxy-4H-1-benzopyran-4-ones with various bases afforded 2,3-dihydro-r-2-aryl-t-3-hydroxy-c-3-(4-nitrophenyl)-4H-1-benzopyran-4-ones in a deprotonation-initiated aryl migration followed by sulfur dioxide extrusion.In the presence of hydroxide and methoxide ions a secondary ring cleavage has also been observed.However, the reaction of trans-2,3-dihydro-2-aryl-3-nosyloxy-4H-1-benzopyran-4-ones with cyanide ions gave 2,3-dihydro-r-2-aryl-t-4-cyano-c-3,c-4-epoxy-4H-1-benzopyrans in a carbonyl attack of cyanide followed by an internal substitution reaction.

FLAVONOIDS, 40. SYNTHESIS OF 3-ALKYL- AND -ARYLTHIOFLAVANONES AND THEIR TRANSFORMATIONS INTO SULFUR-CONTAINING FLAVONOIDS

trans-3-Mesyloxyflavanones 1 were converted into cis- and trans-3-(alkylthio)- and -(phenylthio)flavanones 2-4 by nucleophilic substitution reaction with thiols or thiolates.Flavanones 2-4 were useful intermediates in the synthesis of various sulfur-containing derivatives; flavanones, flavones and dihydrochalcones posessing alkyl- or arylthio, -sulfinyl and -sulfonyl group.Oxidation of cis- and trans- isomers of 4 led to completely different products.