Synthesis and Anticancer Activities of Novel Bis-chalcones Incorporating the 1,3-diphenyl-1H-pyrazole Moiety: In Silico and In Vitro Studies

Abstract

A new series of bis-chalcones 5-10 has been prepared by the condensation reaction of one equivalent of bis(acetophenones) 3a-f with two equivalents of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde 4. The newly prepared compounds 5-10 have been fully characterized and evaluated as in vitro anticancer agents against a panel of human cancer cell lines A431, A549, PC3, and a normal human skin fibroblast BJ1. Aims: the current work designed to explore anti-cancer activity of novel bis-chalcones incorporating 1,3-diphenyl-1H-pyrazol moiety. Background: Chalcones represent one of the most important organic compounds that have been attracting the interest of many researchers in drug discovery. Objective: The present study was carried out to explore anti-cancer activity of novel bis-chalcones incorporating 1,3-diphenyl-1H-pyrazol moiety as in vitro and in silico studies. Materials and Methods: condensation reactions, MTT Assay, Anticancer activity, Gene expression, DNA Fragmentation, DNA Damage and Molecular Docking study. Results: Compounds 5 and 9 were found to be the most promising compounds in the prepared series with IC50 (50.3 and 50.1 µg/ml, respectively,) against epidermoid cancer cell line A431 compared to doxorubicin as a reference drug Conclusion: All of these results showed that chalcones 5 and 9 have promising anti-cancer properties without cytotoxic effect, which could make it a promising active component with further studies).

Cytotoxic Effect of New (E)‐2‐Cyano‐N‐(tetrahydrobenzo[b]thiophen‐2‐yl)acrylamide Derivatives: Down‐Regulation of RBL2 and STAT2 and Triggering of DNA Damage in Breast Carcinoma

“…Based on these facts and in continuation to our research interest in the synthesis of bioactive compounds [3,4,18,26–35] we report herein the synthesis of novel series of cyanoacrylamides linked to tetrahydrobenzo[ b ]thiophene moiety and test their cytotoxic activities against various cancer cell lines using MTT assay.…”

“…Although, this reaction is limited to the reaction of aldehydes or ketones with active methylene compounds, this reaction is very easy and fast compared to the other condensation types, due to the presence of deactivating groups that facilitate deprotonation even with a mild base. This reaction is a key reaction for the synthesis of bioactive precursors such as chalcones [1][2][3][4][5] and cyanoacrylamides. [6][7][8] Acrylamide-containing compounds have been shown to be effective in the treatment of metastatic non-small cell lung cancer and other cancer types.…”