22701-17-3

Upstream product

• 119-64-2 tetralin 
• 491-78-1 5-Hydroxyflavone 
• 699-83-2 2,6-dihydroxylacetophenone 
• 387-46-2 2,6-dihydroxybenzaldehyde 
• 100-52-7 benzaldehyde 
• 78646-28-3 2′-hydroxy-6′-methoxymethoxyacetophenone 
• 25515-44-0 (E)-1-(2,6-dihydroxyphenyl)-3-phenylprop-2-en-1-one 
• 40524-67-2 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 365276-81-9 2-(N-benzyl-α-iminoethyl)-phenol 

Downstream Products

• 99110-93-7 5-hydroxy-3-N,N-dimethylaminomethylidene-flavanone 
• 98769-87-0 4-chloro-3-formyl-5-hydroxy-flav-3-ene 

Relevant academic research and scientific papers

Method and compounds for cancer treatment utilizing NFkB as a direct or ultimate target for small molecule inhibitors

A method is described for cancer treatment through NFκB inhibition. NFκB is a direct or ultimate target for small molecule inhibitors. These small molecule inhibitors are aimed at suppression of NFκB directly or by indirect suppression of IKK, SFK kinases, or other upstream kinases. The present invention includes small molecule inhibitors comprising three, five, and seven carbon unsaturated spacers having one or two carbonyls, flanked by substituted aryl rings. The small molecule inhibitors can be symmetrical or unsymmetrical.

Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones

We describe a facile efficient, and preparative approach for monohydroxyflavanone syntheses. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2′-hydroxychalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatography-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. Ours is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. We are also the first to develop a procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metabolism and oxidation studies.

Reduction of 4H-chromen-4-ylidene amines: synthesis of 2-[(1-aminoalkyl)-3-aryl-2-propenyl] phenols

A procedure for the reduction of 4H-chromen-4-ylidene amines 1 is described, which affords to 2-[(1-aminoalkyl)-3-aryl-2-propenyl] phenols 2, previously unknown in literature. The efficacy of the procedure is compared with alternative synthetic routes.

Synthesis of hydroxyflavanones from substituted acetophenones and benzaldehydes in the presence of silica gel, boric acid and piperidine

Direct synthesis of hydroxyflavanones from appropriately substituted acetophenones and benzaldehydes was achieved in the presence of boric acid, silica gel and piperidine. The formation of flavanones presumably involved the reaction between the acetopheno

CONVERSION OF 2'-HYDROXYCHALCONES TO FLAVANONES CATALYZED BY COBALT SHIFF BASE COMPLEX

Co(salpr) catalyzes the conversion of 2'-hydroxychalcones to flavanones in methanol under oxygen.Base catalysis by Co(salpr) (OH) produced in situ is responsible for the reaction, which is found to proceed reversibly.

Kinetics and Mechanism of the Cyclisation of 2',6'-Dihydroxychalcone and Derivates

pH-Rate profiles are reported for the cyclisation in water to 5-hydroxyflavanones of 2',6'-dihydroxychalcone (1) and its 4-methoxy (2), 3,4-dimethoxy (3), 3,4,5-trimethoxy (4), 2,4,6-trimethoxy (5), 4-chloro (6), and 3,4,4'-trimethoxy (8) derivates.As for the previously studied 2',6'-dihydroxy-4,4'-dimethoxychalcone (7), rate coefficients are established for acid-catalysed cyclisation of neutral chalcone, for unimolecular cyclisation of the neutral, monoanionic, and dianionic chalcone, and for the base-catalysed reverse ring-opening reaction.Cyclisation of the monoanion of 2',6'-dihydroxychalcone is almost 40 times faster than that of the monoanion of the 2'-hydroxy-6'-methoxyhalcone (10) and is also estimated to be about ten times faster than that of the reactive monoanion of 2',4'-dihydroxychalcone.These are the first calculations of the enhancement of rate of monoanion cyclisation by the 6'-OH group.The effect is only small, and is suggested to arise largely from stabilisation of the transition state for ketonisation by hydrogen bonding to enolate oxygen.Other reactivity differences amongst the chalcone monoanions are also discussed.Enthalpy and entropy of activation data are reported for monoanion cyclisation of (1), (2), and (4)-(6).Rate coefficients for the cyclisation of the chalcone monoanions are almost identical for (1)-(4) and (6) in water but not in deuterium oxide: kinetic hydrogen isotope effect (KIE) values are 3.4 (1), 5.7 (2), 4.9 (3), 3.0 (4), 7.5 (5), 2.9 (6), and 5.0 (8).For chalcones (2) and (7), the KIE values of which are both 5.7, the amounts of H versus D incorporation at the flavanone 3-carbon for monoanion cyclisation in H2O/D2O mixtures were established by mass spectroscopy.This gave product (or 'discrimination') isotope effect (PIE) values of 7.9 for (2) and 3.8 for (7), suggesting for (2) but not (7) an inverse effect contribution to KIE from sources other than rate-limiting proton transfer to carbon.Monoanion cyclisation of (1) in D2O was established by 1H n.m.r. as involving almost equal amounts of anti and syn addition of 2'-O- to the enone double bond.Reactivity differences amongst the chalcones for reactions other than monoanion cyclisation are only briefly considered.