Synthesis Process of 1,4-Naphthoquinone Oxime Derivative Compounds with Apoptosis-Inducing and Cell Cycle Arrest Activity in Breast Cancer Cells and Their Produced Products

Abstract

This invention relates to naphthoquinone derivative compounds and their synthesis methods. More specifically, 1,4-naphthoquinone oxime derivatives and the derivative synthesis process by reflux, using THF solvent and DMAP catalyst, as well as their cytotoxic activity against breast cancer cells by inducing apoptosis and cell cycle arrest. The 1,4-naphthoquinone compound which is the starting compound is structurally changed into a naphthoquinone oxime compound. The naphthoquinone oxime derivative compound has selective activity against breast cancer cells compared to the original compound. The selectivity index value of the original compound is 0.964 while the naphthoquinone oxime derivative is 8.48 and the naphthoquinone acetyl oxime derivative is 10.26. Cytotoxic activity against breast cancer cells is indicated by the IC50 values ​​of compounds 1-4, which are 21.10 µM, 10.74 µM, 48.19 µM, and 3.24 µM, respectively. Naphthoquinone oxime derivative compounds can induce apoptosis and cell cycle arrest at concentrations of 1.62 µM - 48.19 µM.The results of this invention can be utilized by academics, research institutions, medical and pharmaceutical industries at the national, regional and international levels for the discovery of new anticancer drugs that are effective and selective in their efficacy and are safe.