24467-41-2

Upstream product

• 100-52-7 benzaldehyde 
• 487-26-3 Flavanone 
• 118-93-4 o-hydroxyacetophenone 
• 888-12-0 (E)-2'-hydroxy-chalcone 

Downstream Products

• 109754-33-8 C₂₃H₁₈N₂O₂ 
• 109754-33-8 C₂₃H₁₈N₂O₂ 
• 121802-89-9 (3S,3aS,4S)-3,4-Diphenyl-3a,4-dihydro-3H-chromeno[4,3-c]pyrazole-2-carboxylic acid amide 
• 121802-90-2 3,4-Diphenyl-3a,4-dihydro-3H-chromeno[4,3-c]pyrazole-2-carbothioic acid amide 
• 142929-08-6 3-<α-(2-Aminoanilino)benzyl>-2-phenylflavanone 
• 24467-44-5 3-benzylidene-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one 
• 119656-93-8 (2R,3R)-3-Bromo-3-(bromo-phenyl-methyl)-2-phenyl-chroman-4-one 
• 119139-39-8 3-(Hydroxy-phenyl-methyl)-2-phenyl-chromen-4-one 
• 4197-99-3 3-benzoyl-4H-chromen-4-one 

Relevant academic research and scientific papers

One-pot synthesis of (E)-3-benzylideneflavanones from 2-hydroxyacetophenones and aromatic aldehydes

An efficient and practical PPA/H2SO4 promoted synthesis of (E)-3-benzylideneflavanones from 2-hydroxyacetophenones and aromatic aldehydes was developed. Various (E)-3-benzylideneflavanones were produced in good to excellent yields.

Biological evaluation of 3-benzylidenechromanones and their spiropyrazolines-based analogues

A series of 3-benzylidenechrmanones 1, 3, 5, 7, 9 and their spiropyrazoline analogues 2, 4, 6, 8, 10 were synthesized. X-ray analysis confirms that compounds 2 and 8 crystallize in a monoclinic system in P21/n space groups with one and three molecules in each asymmetric unit. The crystal lattice of the analyzed compounds is enhanced by hydrogen bonds. The primary aim of the study was to evaluate the anti-proliferative potential of 3-benzylidenechromanones and their spiropyrazoline analogues towards four cancer cell lines. Our results indicate that parent compounds 1 and 9 with a phenyl ring at C2 have lower cytotoxic activity against cancer cell lines than their spiropyrazolines analogues. Analysis of IC50 values showed that the compounds 3 and 7 exhibited higher cytotoxic activity against cancer cells, being more active than the reference compound (4-chromanone or quercetin). The results of this study indicate that the incorporation of a pyrazoline ring into the 3-arylideneflavanone results in an improvement of the compounds’ activity and therefore it may be of use in the search of new anticancer agents. Further analysis allowed us to demonstrate the compounds to have a strong inhibitory effect on the cell cycle. For instance, compounds 2, 10 induced 60% of HL-60 cells to be arrested in G2/M phase. Using a DNA-cleavage protection assay we also demonstrated that tested compounds interact with DNA. All compounds at the concentrations corresponding to cytotoxic properties are not toxic towards red blood cells, and do not contribute to hemolysis of RBCs.

The relationship between Hirshfeld potential and cytotoxic activity: A study along a series of flavonoid and chromanone derivatives

The present study examines a series of six biologically-active flavonoid and chromanone derivatives by X-ray crystal structure analysis: (E)-3-benzyl-idene-2-phenyl-chroman-4-one, C 22 H 16 O 2, I, (E)-3-(4-methyl-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 2, II, (E)-3-(3-methyl-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 2, III, (E)-3-(4-meth-oxy-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 3, IV, (E)-3-benzyl-idenechroman-4-one, C 16 H 12 O 2, V, and (E)-3-(4-meth-oxy-benzyl-idene)chroman-4-one, C 17 H 14 O 3, VI. The cytotoxic activities of the presented crystal structures have been determined, together with their inter-molecular inter-action preferences and Hirshfeld surface characteristics. An inverse relationship was found between the contribution of C?C close contacts to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line. Dependence was also observed between the logP value and the percentage contribution of C?H contacts to the Hirshfeld surface.

3-benzylidenyl-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-ketone compounds

The invention relates to 3-benzylidenyl-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-ketone compounds, a preparation method and an application. The preparation process of the compounds is shown as follows:components including 2-hydroxyphenylacetone, aromatic al

Structure-cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones

The E,Z-isomers of 3-arylidene substituted flavanone, chromanone and 3-aryl substituted flavone derivatives were tested in vitro for their cytotoxic activity against three cancer cell lines (HL-60, NALM-6, WM-115) and normal cell line (HUVEC). It was observed that substitution at C3 position led to significant enhance in cytotoxicity. Isomeric configuration of 3-arylideneflavanones had an influence on the cytotoxic potential. Multiple regression analysis combined with variable selection by genetic algorithm was used to model relationships between molecular descriptors and the cytotoxic activity. The most accurate QSAR models were based on a combination between energy of LUMO, experimental value of log P and partial charge on carbonyl oxygen (δO2).

Reactivity of α-arylidene benzoheteracyclanone dibromides toward azide ion: An effective approach to 3-(α-substituted-benzyl)chromones and -1-thiochromones

Treatment of dibromides of 3-arylidenechromanones and -1-thiochromanones with sodium azide resulted in the formation of 3-(α-azidobenzyl)chromones and -1-thiochromones whereas dibromides having no antiperiplanar vicinal hydrogen in the ring such as flavanone, 1-thioflavanone and benzosuberone derivatives afforded only the parent enones by bromine elimination. Evidence supported the intermediacy of 3-(α-bromobenzyl)chromones and -1-thiochromones in this reaction. These postulated intermediates were prepared in an independent way and transformed into azides in high yield.

Alkali-catalysed condensation of flavanones and aromatic aldehydes : Synthesis of E-3-arylideneflavanones and related compounds

Poor solubility of E-3-arylideneflavanones and their heterocyclic analogues in aqueous alcohols has been utilised for alkali-catalysed synthesis of a number of such compounds starting either from 2′-hydroxychalcones or from o-hydroxyacetophenones. Among s

3-Arylideneflavanones. Part 2: Reaction with diazomethane

3-Arylideneflavanones 1-9 were treated with diazomethane. As a result, the following compounds were obtained: the 3-spiropyrazolines (structure A)-2'-phenylchromanone-3'-spiro-3,4-phenyl-1-pyrazoline (1a) and its 3''- and 4''-derivatives (2a-9a), the 4-spiropyrazolines (structure B) 2'-phenylchromanone-3'-spiro-4-1H-5-phenyl-2-pyrazoline (1b) and the 4''-cyano (7b) and 3''-nitro (8b) derivatives; and the methylation product (structure C) 3-(4-N,N-diethyl-amino-β-methylbenzylidene)flavanone (5c).

NMR spectral studies of several series of E-3-arylideneflavanones: Realisation of some steric and electronic interactions

H-2 of E-3-arylideneflavanones differing only in the β-phenyl group is found to experience a reverse substituent chemical shift (s.c.s.) effect.An unfavourable steric interaction between this proton and the ortho-protons of β-phenyl group has been related to this observation.An interesting feature in the 1H NMR spectra of the heterocyclic analogs 5a-c is the significant deshielding of H-2 and shielding of H-β in the case of 5a.Intramolecular hydrogen bond formation between H-2 and the furano oxygen of 5a is probably responsible for this observation.From a studyof the 1H and 13C NMR spectral features of 8a-e which differ only in the 4'-substituent, it may be concluded that a 4'-substituent can polarise the C3-C-β and C=O ?-bonds as well as the ?-system of ring-A.The results of dual substituent parameter analysis of s.c.s. values of C-3, C-β, C-4, C-8a and C-6 for the series 8 have also been presented.