77015-47-5Relevant academic research and scientific papers
Structure-cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones
Kupcewicz, Bogumi?a,Balcerowska-Czerniak, Grazyna,Ma?ecka, Magdalena,Paneth, Piotr,Krajewska, Urszula,Rozalski, Marek
, p. 4102 - 4106 (2013/07/26)
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
Patonay,Dinya,Lévai,Molnár
, p. 2895 - 2907 (2007/10/03)
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.
NMR spectral studies of several series of E-3-arylideneflavanones: Realisation of some steric and electronic interactions
Mallik, Uttam K,Saha, Murari M,Mallik, Asok K
, p. 753 - 758 (2007/10/02)
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.
Flavonoids. Part 6. The Kinetics and Mechanism of Base-catalysed Isomerisation of 3-Arylideneflavanones
Dhavale, Dilip Dattatraya,Joshi, Poonam,Marathe, Keshav Gangadhar
, p. 449 - 452 (2007/10/02)
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
