112014-56-9Relevant academic research and scientific papers
Biological evaluation of 3-benzylidenechromanones and their spiropyrazolines-based analogues
Adamus-Grabicka, Angelika A.,Budzisz, Elzbieta,Cieslak, Marcin,Hikisz, Pawe?,Królewska-Golinska, Karolina,Kusz, Joachim,Ma?ecka, Magdalena,Markowicz-Piasecka, Magdalena
, (2020)
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.
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
