77015-45-3

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 487-26-3 Flavanone 
• 112014-64-9 2-Phenyl-3-[1-p-tolyl-meth-(Z)-ylidene]-chroman-4-one 

Downstream Products

• 112014-64-9 2-Phenyl-3-[1-p-tolyl-meth-(Z)-ylidene]-chroman-4-one 
• 119139-29-6 4''-methyl-3-α-hydroxybenzylflavone 

Relevant academic research and scientific papers

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.

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).

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).

Flavonoids. Part 6. The Kinetics and Mechanism of Base-catalysed Isomerisation of 3-Arylideneflavanones

Base-catalysed Z->E conversion of 3-arylideneflavanones provide a unique system suitable for kinetic studies by 1H n.m.r. spectroscopy.Isomerisation studies of 10 enones in pyridine showed that a first-order unimolecular reaction was taking place.The