Abstract

Aim and Objective: Pyrazolo pyridine skeleton is an interesting class of heterocycles due to its diverse biological properties including antitumor, antioxidant and antibacterial activities. The objective of this work was established in vitro antiproliferative activities against MCF-7 (breast cancer) human cell lines for of the synthesized compounds IIIa-e. The effect of the molecular and electronic structures on the biological activity was performed to compare the theoretical data with the experimental observations.

Material and Method: The synthesized compounds were prepared by conventional heating and microwave irradiation technique. The structure of the prepared compounds was confirmed by different spectroscopic tools. The compounds IIIa-e was tested for antitumor activity against breast cancer cell line. The quantum chemical, molecular docking and SAR studies were performed for the prepared compounds.

Results: The microwave irradiation as a source of energy was used to improve the yield and to reduce the time of the reaction. Under this technique, the reaction time was reduced from 4-8 hours to 15-25 min. The yield of the reactions was increased from 81% to 92%. Also, the obtained products were cleaner.

Conclusion: The quantum chemical descriptors confirmed that inhibitor1-(4-methoxyphenyl)-3-(1-methyl-1Himidazol- 4-yl)-6-phenyl-1H-pyrazolo[3,4-b]- pyridine-4-ol (IIIb) is the most potent and reactive among the investigated compounds. This conclusion is congruent with the results obtained experimentally.

Keywords: 5-aminopyrazole, imidazolyl pyrazolopyridine, antitumor, DFT study, molecular docking, SAR.