Fused carbo/heterocyclic 1,4-dihydropyridine (1,4-DHPs) derivatives have been synthesized using β-cyclodextrin an efficient catalyst in alcohol with high yields and purity under one-pot method. The structures of synthesized compound were established using 1H, 13C-NMR, IR, ESI-MS and elemental analysis. The synthesized fused heterocyclic 1,4-DHPs were found to exhibit potent antimicrobial activity as compared to carbocyclic 1,4-DHPs and these results were further supported by percentage structure similarity using Chem 3D software with the standard antibiotic drug (Cefixime). Moreover, heterocyclic 1,4-DHPs shows excellent DNA photocleavage potential using agarose gel electrophoresis.