125574-15-4Relevant articles and documents
Synthesis and in-silico molecular modelling, DFT studies, antiradical and antihyperglycemic activity of novel vanadyl complexes based on chalcone derivatives
Kaur, Mandeep,Kaushal, Raj
, (2022/01/13)
Diabetes mellitus (DM) will be one of the ten most deadly diseases in the near future, according to a WHO survey. It is, therefore, of utmost importance to design and synthesize effective inhibitors to be used in the treatment of DM disease. In this respect, a new series of chalcone derivatives and their vanadyl complexes of composition [VO(LI-III)2]SO4 and [VO(LIV)2] (where LI=1-(2-Hydroxy-phenyl)-3-phenyl-propenone, LII=1-(1-Hydroxy-naphthalen-2-yl)-3-phenyl-propenone, LIII = 1-(2-Amino-phenyl)-3-phenyl-propenone, LIV = 4-Hydroxy-6-methyl-3-(3-phenyl-acryloyl)-pyran-2-one) were designed and synthesized in this work. Physioanalytical, FTIR, 1H NMR, 13C NMR, UV-Visible, EPR, SEM, EDX, and mass spectrometry data were used to establish their formation and validate their structures. After that, biological effects such as antiradical, α-glucosidase, and α-amylase inhibitory activities of synthesized vanadyl-chalcone complexes were assessed. Furthermore, the Density Functional Theory (DFT) studies with 6-31G*/B3LYP level were used to achieve optimal molecular geometries and HOMO-LUMO gap to analyze the chemical and kinetic stability of the complexes. Molecular docking studies were performed as well to investigate the interactions between the synthesized complexes and target enzyme viz. α-amylase and α-glucosidase. The in-vitro biological studies showed major and significant improvements upon the complexation of ligands. Complex 3 (for α-glucosidase) and complex 4 (for α-amylase), in particular, were found to have a remarkable ability to lower blood sugar levels. Otherwise, the potent α-glucosidase and α-amylase inhibitory activity was observed in all of the synthesized complexes. The complexes with the best IC50 values were studied further in terms of enzyme kinetics and displayed mixed inhibition with both enzymes. Furthermore, using the DPPH assay, the antiradical activity of chalcones and their vanadyl complexes was evaluated for their efficacy in releasing oxidative stress. From the obtained results, complex 3 and 4 exhibited remarkable antiradical activity.
Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents
Dong, Jinyun,Huang, Guang,Zhang, Qijing,Wang, Zengtao,Cui, Jiahua,Wu, Yan,Meng, Qingqing,Li, Shaoshun
, p. 1606 - 1614 (2019/09/30)
A series of benzochalcone derivatives have been synthesized and evaluated for CYP1 inhibitory activity and cytotoxic properties against wild type cell lines (MCF-7 and MDA-MB-231) and drug resistant cell lines (LCC6/P-gp and MCF-7/1B1). All of these compounds were found to have selective inhibition towards CYP1B1 and the most potent two possessed single-digit nanomolar CYP1B1 potency. In addition, some of them showed promising cytotoxic activities not only against wild type cells, but also against drug resistant cells at low micromolar concentrations. More importantly, these multi-functional compounds may surmount drug-drug interactions that frequently occur during the combination of CYP1B1/P-gp inhibitors and anticancer drugs to overcome drug resistance. This study may provide a good starting point for the further development of more potent multi-functional agents with CYP1B1 inhibitory activity and cytotoxic potency in cancer prevention and treatment.
Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone-Flavanone Molecular Switch Scaffold
Muller, Brian M.,Litberg, Theodore J.,Yocum, Reid A.,Pniewski, Chanté A.,Adler, Marc J.
, p. 5775 - 5781 (2016/07/13)
Previous work on the o-hydroxychalcone/flavanone molecular switching scaffold showed that simple substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch's scope, scaffolds able to have multiple switching events were also investigated.
