SYNTHESIS OF 2-(2-(2-(BIS (2-CHLOROETHYL) AMINO) ETHOXY) BENZYLIDENE) BENZOFURAN – 3(2H) – ONE DERIVATIVES ON BASIS OF BENZALDEHYDES AND ACETOPHENONES FOR ITS CYTOTOXIC ACTIVITYAbstract
Benzofuranones and nitrogen mustards have been reported as highly potential alkylating agents; with this evidence, the synthesis of some benzofuranones fused with nitrogen mustards was planned and was subjected to in-vitro cytotoxic studies. Substituted benzofuranones were synthesized by condensation of 2-hydroxy benzaldehydes and substituted 2-hydroxy acetophenones and further fused with nitrogen mustards gave high yields of target compounds 2 – (2 – (2 – (Bis (2 -chloroethyl) amino) ethoxy) benzylidene) benzofuran-3(2H)-one derivative. The derivatives synthesized had various halo substitutions such as chloro, bromo, fluro and methyl chloro derivatives. These synthesized compounds were characterized by FTIR, 1H NMR and LCMS spectral studies. Further, the synthesized compounds were subjected to 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide assay on human lung carcinoma cells, A-549 and breast cancer cells, MCF-7 for its in-vitro cytotoxic activity. All the synthesized compounds showed promising cytotoxic activity in which AN– O – 04, (Z) – 2 – (2 – (2 – (bis (2 -chloroethyl) amino) ethoxy) benzylidene) -5 – chloro – 6-methylbenzofuran-3(2H)-oneshowed minimum CTC-50 of 119.32 ± 8.98 and 82.18 ± 6.23 for A-549 and M-549 cell lines respectively which indicates the potency of the synthesized compounds against A-549 and MCF-7 cell lines.
A. R. Mahesh * and V. Murugan
Department of Pharmaceutical Chemistry, College of Pharmaceutical Sciences, Dayananda Sagar University, Bengaluru, Karnataka, India.
17 March 2020
18 June 2020
25 June 2020
01 March 2021