The in-vitro antimicrobial and antioxidant activities of some 2-(9H-fluorene-2-yl)-3-(substituted phenyl)bicyclo [2.2.1]hept-5-ene-2-yl methanones by disc-diffusion as well as serial dilution against their microbial strains and DPPH radical scavenging activities. The titled substrates were synthesized by environmentally benign water mediated Diels-Alder reaction of 9H-2-fluorenyl chalcones and cyclopentadiene in good yields. Conclusion: The present results confirm the positive correlation between the acute phase response of inflammation and oxidative stress in non-diabetic and diabetic obese subjects.