Synthesis, molecular docking and modeling of new acenaphthenequinones clubbed of anticancer

Abstract

The acenaphthenequinone-thiosemicarbazone (1) was utilized as a precursor for the synthesis of 2-(2-(5-acetyl-4-methylthiazol-2-yl)hydrazono)acenaphthylen-1(2H)-one (3) by applying Hantzsch-type reaction 3‑chloro-2,4-pentanedione (2). Claisen–Schmidt reaction of 3 with 4-chlorobenzaldehyde furnished the corresponding thiazolyl-chalcone 4, which underwent cyclization upon treatment with hydrazine hydrate or phenyl hydrazine to produce the corresponding thiazolyl-pyrazoles 5 and 6, respectively. All of the structures of these synthesized compounds were elucidated by elemental analysis and the spectral analysis such as IR, 1HNMR and mass spectroscopy. The DFT calculated Mulliken's atomic charge was used to represent the activity of the synthesized derivatives. While, the theoretical study of molecular docking was applied to expect their reactivity towards 5ORO protein. In addition, the synthesized analogues were examined against different cancer cell lines. All of theoretical and experimental studies were represented a good correlation with the anticancer activities for the synthesized derivatives.