Organic Communications

In this study, the synthesis and characterization of 2-(2-fluorobiphenyl-4-yl)-N´-[(substituted methylene]propanehydrazides (3a-s) and 2-(2-fluoro-[1,1'-biphenyl]-4-yl)-N-(5-methyl-2-(substituted aryl)-4-oxothiazolidin-3-yl)propanamides (4a-s) are described and also the antiproliferative effect of the compounds on  HT-29,  HeLa, A549 and MCF-7 cancer cell lines is investigated. Additionally, mouse embryonic fibroblast cells NIH3T3 were also evaluated to determine the selectivity. The results showed that the identified compounds did not cause any toxicity against NIH3T3 cell line. Moreover, N-(2-(3,5-Bis(trifluoromethyl)phenyl)-5-methyl-4-oxothiazolidin-3-yl)-2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanamide (4h) had the most growth inhibitory effect (55.97% inhibition) on HT-29 colorectal adenocarcinoma cell line. The results obtained from the study show that the compound 4h, which has no cytotoxic effect on normal cells, may be an alternative in the treatment of colon cancer.

Inhibition of soluble epoxide hydrolase (sEH) is implicated as a new therapeutic approach against inflammatory disorders in the context of metabolic and cardiovascular diseases. In the course of our ongoing research on sEH inhibitors, we synthesized novel piperididine/piperazine amide derivatives of the chromone-2-carboxylic acid, and evaluated their inhibitory properties against human sEH. The chemical structures of the target compounds (2-5, 7-9) were elucidated by means of 1H-NMR, 13C-NMR and HRMS spectra. Initial screening of final compounds against sEH at a final concentration of 10 micromolar led to the identification of compound 7, which inhibited sEH activity in a concentration-dependent manner with an IC50 = 1.75 m​​​​​icromolar. Therefore, this chromen-2-amide derivative 7 decorated with benzyl piperidine on the amide side can be regarded as a novel lead structure, which pave the way of developing new analogues with improved inhibitory activities against sEH.

Imidodithiocarbonate derivatives containing pyrimidine ring, potentially functional molecules were synthesized and characterized. FTIR, 1H NMR and 13C NMR spectroscopy and elemental analysis methods were used for characterization. The obtained compounds were screened for their antioxidant capacity using DPPH (1,1-diphenyl-2-picrylhydraziyl) free radical-scaving and ABTS (2,2’-azino-bis(3-ethylbenzothiazoline-6-sulphonicacid) assays. The possible interactions between the molecular docking calculations of the synthesized imidodithiocarbonate derivatives and their binding potentials to the active sites of target enzymes.