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In this article, we describe the synthesis and biological evaluation of a novel 2-(methylamino)-3-nitro-4-(4-oxo-4Hchromen-3-yl) pyrano[3,2-c]chromen-5(4H)-one (CCN). It is also determined that CCN impregnated into the collagen scaffold has the potential to mimic the function of the extracellular matrix as a biomaterial in the field of tissue engineering. The series of pyrano[3,2-c]chromen-5(4H)-one derivatives (4a-4j), were analyzed by 1 H NMR, 13 C NMR, Mass spectral and FTIR analysis. The compound 4c confirmed by single crystal XRD studies. All the compounds were screened for antimicrobial activity against the gram positive, gram negative bacteria and yeast. Among all the compounds, the compound (4a=CCN) showed activity against Gram positive and Gram negative bacteria, when compared to the synthesized compounds. Further the compound CCN was evaluated for cytotoxicity against MCF-7, Hep-2 and Vero cancer cell lines with IC50 values of 5.4 µg/ml, 5.3 µg/ml and 68.4 µg/ml respectively. In addition, the result of flow cytometry and docking ((PDBID: 1A27 with the ligand) study were supported to the activity of the synthesized compound (4a). The FTIR and NMR analysis of the CCN impregnated collagen scaffold were done to reveal the existence of CCN molecule in the scaffold. The inherent property of the collagen scaffold was not significantly affected by structure of CCN molecule. The thermal and mechanical properties of the collagen scaffold impregnated with CCN molecule gives stability as well as supports the swelling. However, the COL-CCN scaffold showed an enhanced cell attachment and proliferation of NIH 3T3 fibroblast cells. Based on the results, the novel CCN molecule impregnated with collagen scaffold has the potential application as a biomaterial in tissue engineering.