Synthesis of 1-(Indol-2-yl)-phenoxazine hybrids from quinacetophenone precursors and their biological evaluation as DNA intercalating agents

Authors：Nunewar, Saipra*** N.; Kotla, Naveen; Uppu, Jaya Lakshmi; Dixit, Apoorva; Pooladanda, Venkatesh; Godugu, Chandraiah; Tangellamudi, Neelima D.

Source：Journal of Molecular Structure, 2020, 1217: 128311.

DOI：10.1016/j.molstruc.2020.128311

• CONVENIENT SYNTHESIS
• POT SYNTHESIS
• DESIGN
• MOLECULES
• INHIBITORS
• HYDROQUINONES
• ALKOXYLATION
• DERIVATIVES
• CHEMISTRY
• DISCOVERY

An operationally simple reaction between quinacetophenone and aniline derivatives in the presence of triethylamine at room temperature afforded 1-(indol-2-yl)-phenoxazine hybrids in good yields. This unique transformation proceeds via sequential aza-Michael attack and imine formation to yield 1-(indol-2-yl)-phenoxazine hybrids. The most plausible reaction mechanism was established based on the mechanistic studies carried out with Mass spectrometry.The synthesized molecules were subjected to in-vitroanti-proliferative evaluation on various cancer cell lines by MTT assay where compound 8was found to display signifiacnt IC50 value of 3.71?±?0.57?μM on A-549?cell line. The ability of compound 8 to intercalate DNA was also confirmed by DNA Nanodrop method and viscosity experimental studies.