A novel synthetic methodology for preparation of (Z)-N'-(1-((bis(2-chloroethyl)amino)methyl) -2-oxoindolin-3-ylidene)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzohydrazide derivatives VIII(a-j) were prepared by Paal-knorr, Mannich base and Schiff’s base reactions. The newly synthesized compounds structures was confirmed by FT-IR, 1H-NMR, 13C-NMR and MASS spectrometry. The percentage yield of the newly synthesized compounds ranged between 75-91%. All the compounds were evaluated for in vitro anticancer activity by MTT assay method against MCF-7, A549, HEPG2 cell lines and antioxidant activates by DPPH method. Compounds VIII-b, VIII-h, and VIII-I exhibited the highest activities against three cancer cell lines with IC50ranging from 149.16μg/ml to 229.86μg/ml(MCF-7), 95.31μg/ml to 298.29μg/ml (A549), and 115.8μg/ml to 177.83μg/ml (HepG2), while compound VIII-h was found to be most potent against A549 cell line. From the results of antioxidant study, compounds VIII-c, VIII-e, VIII-f, and VIII-h possess much higher radical scavenging activity in DPPH parameter compared to standard used.