40649-77-2

Upstream product

• 135-19-3 β-naphthol 
• 100-52-7 benzaldehyde 
• 574-19-6 1-(2-hydroxy-1-naphthyl)ethan-1-one 
• 2860-03-9 3-phenyl-2,3-dihydro-1H-benzo[f]chromen-1-one 
• 140-10-3 (E)-3-phenylacrylic acid 
• 93-04-9 2-Methoxynaphthalene 
• 102-92-1 Cinnamoyl chloride 
• 621-82-9 Cinnamic acid 
• 76339-56-5 2-naphthylcinnamate 
• 60983-66-6 2'-difluoroboroxy-5',6'-benzochalcone 

Downstream Products

• 2860-03-9 3-phenyl-2,3-dihydro-1H-benzo[f]chromen-1-one 
• 1413433-51-8 C₁₉H₁₄O₂ 
• 960505-59-3 (E)-1-(3-phenylprop-2-enoyl)naphthalen-2-yl nonafluorobutanesulfonate 
• 1456866-23-1 2-methoxy-3-phenyl-1H-benzo[f]chromen-1-one 
• 1195566-85-8 2-hydroxy-3-phenyl-1H-benzo[f]chromen-1-one 
• 6051-87-2 3-phenyl-1H-naphtho[2,1-b]pyran-1-one 
• 152598-54-4 Co(OC₁₀H₆C₃H₄N₂C₆H₅)2(C₅H₅N)2 
• 152579-16-3 Ni(OC₁₀H₆C₃H₄N₂C₆H₅)2(C₅H₅N)2 
• 152579-10-7 Cu(OC₁₀H₆C₃H₄N₂C₆H₅)2 
• 152579-19-6 Co(OC₁₀H₆C₃H₄N₂C₆H₅)2(H₂O)2 
• 152598-57-7 Zn(OC₁₀H₆C₃H₄N₂C₆H₅)2 
• 166761-74-6 3-(2-hydroxy-1-naphthyl)-5-(phenyl)-2-isoxazoline 

Relevant academic research and scientific papers

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone-Flavanone Molecular Switch Scaffold

Previous work on the o-hydroxychalcone/flavanone molecular switching scaffold showed that simple substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch's scope, scaffolds able to have multiple switching events were also investigated.

A new solid acid catalyst FeCl3/bentonite for aldol condensation under solvent-free condition

For the first time, a new solid acid catalyst has been used for the synthesis of aryl chalcones under solvent free conditions. A simple method (solid dispersion method) has been adopted for the synthesis of FeCl3/bentonite. The prepared catalyst has been characterized by different characterization techniques. A series of E-1-(substituted phenyl)-3-(1-pyrenyl)-2-propen-1-ones have been synthesized using FeCl3/bentonite under microwave-assisted solvent-free conditions. The yields are in the range from 80 to 88%. All the synthesized chalcones have been characterized by their physical constants, analytical, IR, 1H and 13C NMR spectral data. This catalyst can be reused for further runs (after fifth cycle) without decrease in activity. This catalyst gives excellent yields and is inexpensive and easily recyclable for this reaction.

Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2

Multidrug resistance (MDR) often leads to a failure of cancer chemotherapy. Breast Cancer Resistance Protein (BCRP/ABCG2), a member of the superfamily of ATP binding cassette proteins has been found to confer MDR in cancer cells by transporting molecules with amphiphilic character out of the cells using energy from ATP hydrolysis. Inhibiting BCRP can be a solution to overcome MDR.We synthesized a series of flavones, 7,8-benzofl avones and 5,6-benzo flavones with varying substituents at positions 3, 3′ and 4′ of the (benzo)fl avone structure. All synthesized compounds were tested for BCRP inhibition in Hoechst 33342 and pheophorbide A accumulation assays using MDCK cells expressing BCRP. All the compounds were further screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity by calcein AM accumulation assay to check the selectivity towards BCRP. In addition most active compounds were investigated for their cytotoxicity. It was observed that in most cases 7,8-benzoflavones are more potent in comparison to the 5,6-benzoflavones. In general it was found that presence of a 3-OCH3 substituent leads to increase in activity in comparison to presence of OH or no substitution at position 3. Also, it was found that presence of 3′,4′-OCH3 on phenyl ring lead to increase in activity as compared to other substituents. Compound 24, a 7,8-benzoflavone derivative was found to be most potent being 50 times selective for BCRP and showing very low cytotoxicity at higher concentrations.

Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein

Breast cancer resistance protein (BCRP/ABCG2) belongs to the ATP binding cassette family of transport proteins. BCRP has been found to confer multidrug resistance in cancer cells. A strategy to overcome resistance due to BCRP overexpression is the investigation of potent and specific BCRP inhibitors. The aim of the current study was to investigate different multi-substituted chalcones for their BCRP inhibition. We synthesized chalcones and benzochalcones with different substituents (viz. OH, OCH3, Cl) on ring A and B of the chalcone structure. All synthesized compounds were tested by Hoechst 33342 accumulation assay to determine inhibitory activity in MCF-7 MX and MDCK cells expressing BCRP. The compounds were also screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity in the calcein AM accumulation assay and were found to be selective towards inhibition of BCRP. Substituents at position 2′ and 4′ on chalcone ring A were found to be essential for activity; additionally there was a great influence of substituents on ring B. Presence of 3,4-dimethoxy substitution on ring B was found to be optimal, while presence of 2- and 4-chloro substitution also showed a positive effect on BCRP inhibition.

Asymmetric ion-pairing catalysis of the reversible cyclization of 2'-hydroxychalcone to flavanone: Asymmetric catalysis of an equilibrating reaction

The asymmetric catalytic cyclization of the simple 2'-hydroxychalcone (1) to flavanone (2), a model for the chalcone isomerase reaction, has been realized as a catalytic asymmetric ion-pairing process with chiral quaternary ammonium salts (e.g., 9-anthracenylmethlycinchoninium chloride; 9-Am-CN-Cl) and NaH as small-molecule co-catalyst. In toluene/CHCl3 solution, the process reaches an intrinsic enantioselectivity of up to S = 14.4 (er = 93.5:6.5). The reversible reaction proceeds in two steps: A fast initial reaction approaches a quasi-equilibrium with KR/S = 4.5, followed by a second, slow racemization phase approaching Krac = 9. A simple mechanistic model featuring a living ion-pairing catalysis with full reversibility is proposed. Deuterium transfer from co-solvent CDCl3 to product 2 and isolation of a Michael conjugate formed from 2 and 1 demonstrate the intermediacy of flavanone enolate ion pairs. A kinetic model shows good agreement with the experimentally observed, peculiar, time-dependent evolution of the species concentrations and the enantiomeric excess of 2. The reaction is a chemical model of the chalcone isomerase enzymatic reaction. Furthermore, it is an ideal model for studying the characteristic behavior of reversible asymmetric catalyses close to their equilibria.

Solution phase photocyclisation reaction of 2-hydroxychalcones to 4-flavanones

The photochemical cyclisation of 2-hydroxychalcones leading to the synthesis of 4-flavanones in solution phase has been investigated. The formation of photoproducts has been explained on the basis of excited state intramolecular proton transfer (ESIPT) and the cyclisation efficiency of the chalcones has been found to depend upon the electron density on the phenolic oxygen as well as on the carbonyl group. This synthesis of flavanones by photoirradiation is an eco-friendly route with comparative yield to those of thermal methods. Although the molecular skeletons of these substrates is amenable to cis-trans isomerisations and cycloadditions but no photoproducts corresponding to these reactions have been realized.

Synthesis of chiral 3-substituted indanones via an enantioselective reductive-heck reaction

(Chemical Equation Presented) An efficient intramolecular palladium-catalyzed, asymmetric reductive-Heck reaction has been developed, which allowed for the synthesis of either enantiomerically enriched 3-substituted indanones or α-exo-methylene indanones depending on the base used.

Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines

Five new 1,3,5-triphenyl-2-pyrazolines were synthesised by reacting 1,3-diphenyl-2-propene-1-one with phenyl hydrazine hydrochloride and another five new 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines were synthesised by reacting 1-(2′-hydroxy

The reactions of phenols with α,β-unsaturated aromatic acids in presence of polyphosphoric acid: Synthetic and mechanistic studies

The reactions of cinnamic acid with phenol itself, catechol, hydroquinone, pyrogallol and 2-naphthol in presence PPA were studied and that with resorcinol was reinvestigated. With phenol itself and hydroquinone were obtained 3,4-dihydro-4-phenylcoumarin (1r) and 6-hydroxy-3,4-dihydro-4-phenylcoumarin (1s), respectively, as the sole products. Catechol and pyrogallol, on the other hand, afforded, besides the corresponding 3,4-dihydrocoumarins, viz. 8-hydroxy-3,4-dihydro-4-phenylcoumarin (1t) and 7,8-dihydroxy-3,4-dihydro-4-phenylcoumarin (1u), as the major products, 5,6-dihydroxy-3-phenylindanone (5b) and the chalcone 1-(2′,3′,4′-trihydroxy)-3-phenylpropan-2-en-1-one (3d), respectively, as minor products. But contrary to earlier observation, resorcinol was found to give 7-hydroxy-3,4-dihydro-4-phenylcoumarin (1v) instead of 7-hydroxyflavanone (4e). 2-Naphthol, on the other hand, afforded the chalcone derivative 1-|2′-hydroxynaphthyl|-3-phenylpropan-2-ene-1-one (7) as the exclusive product. The yields of the major products in the above reactions were 50-67% except that with phenol itself yielding 1r in 40% yield. The structures of all the products 1r, 1s, 1t, 1u, 1v, 3d, 5b and 7 were established from their various spectral (IR, 1H and 13C NMR and mass) data. Evidence for plausible mechanisms of formation of the above products was provided.