Synthesis, Characterization, Molecular Docking Studies of Substituted 2-Amino 3-Chloro Naphthoquinone Derivatives and their Pharmacological Assessment

The present study deals with designing of some novel substituted 2 -amino 3-chloro naphthalene – 1,4 dione derivatives on the basis reaction between 2,3-dichloronaphthalene -1,4-dione and various secondary amine like 5-amino uracil (L1), 5-amino 1, 3-dimethyl uracil (L2), 2-amino-chromen (L3), 2-aminofuran (L4) and isonicotinohydrazide (L5) in presence of ethanol. • The synthesized compounds were characterized by IR, 1H NMR, 13C NMR, Mass spectrometry and elementary analysis. • Preliminary QSAR study was carried out for the synthesized compounds. All the compounds obeyed the Lipnski rule of 5. • Solubility characters of synthesized compounds were carried out by using various solvents. The tested compounds are freely soluble in DMSO, soluble in chloroform and methanol, slightly soluble in acetone, ethyl acetate and ethanol and insoluble in water. • The structures of the synthesized compounds were studied using Autodock software against Topoisomerease II as a target enzymes. The docking results showed that Compounds L3, L2, L4 and L1 were found to have significant binding score against target enzyme Topoisomerase compared to standard drug Etaposide. • Compounds L3 andL2 were allowed only 15.9 and 24.1% cell growth at the conc. of 80 μg / ml respectively where as other compounds has showed 25 – 78% cell growth when compared to Standard Adrimycin. This results indicated that the studied compounds exhibit the Invitro Anti- cancer activity against the Breast cancer cell line MCF-7. • A series of 1,4-naphthoquinone derivatives were synthesized and investigated for their cytotoxic activity against MCF – 7 cell lines. Novel anticancer agents such as compound L2 and L3 exhibited the most potent cytotoxic activity against MCF – 7 cell lines. • The study may be concluding that the effects of substituents at the 2-amino position on the naphthoquinone core structure and its corresponding influence on the cytotoxic activity