A series of 25 new spirocarbocycles were synthesized by a three component reaction that involves few cyclic nucleophiles, vinyl malononitriles and aldehydes with variable substitution patterns. All the synthesized compounds were evaluated for their antimicrobial activity and the compounds showed significant activity. Synthesized compounds 4c, 4i and 6i showed good anticancer activity against A549 cancer cell line. Molecular docking studies indicated that compound 4i had the greatest affinity for DNA gyrase receptor than others and compound 6i had the greatest affinity for anaplastic lymphoma kinase (ALK) receptor. These compounds can be better therapeutic agents for microbial and cancer cell lines.