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In this study, Schiff bases were synthesized by utilizing the reaction of 4‐ and 5‐aminoindane with substituted benzaldehydes. After the reduction of isolated Schiff bases with NaBH4, the corresponding secondary amine derivatives were obtained. The structures of all synthesized molecules were confirmed by 1H‐NMR, 13C‐NMR, FTIR, and ESI‐MS. Antioxidant activities of all synthesized molecules were investigated by DPPH method, and IC50 values were calculated. In addition, antibacterial activities of targets were investigated by the well diffusion method, and then MIC99 values were calculated. While only four of the sixteen synthesized molecules showed a high level of antioxidant activity, all of the molecules exhibited biological activity against gram‐positive and gram‐negative bacteria to varying degrees. In addition, all the synthesized molecules showed high antifungal activity. In antioxidant capacity studies, the IC50 values of 2‐(((2,3‐dihydro‐1H‐inden‐5‐yl)amino)methyl)‐6‐methoxyphenol (4d) and 2‐(((2,3‐dihydro‐1H‐inden‐4‐yl)amino)methyl)‐6‐methoxyphenol (7d) were determined to be 18.1 µg and 35.1 µg, respectively, and these values are much stronger than BHT (butylated hydroxytoluene) and BHA (butylated hydroxyanisole) used as positive controls. The fact that targets have the same core structure with different substituents has revealed a good structure‐activity relationship.

The electrophilic addition of bromine to bicyclo[4.2.0]oct-3-en-7-one in CHCl3 at 0  C led to 60% yield of trans-and 30% yield of cis-dibromide. The structure of the synthesized molecules was determined using 1 H and 13 C NMR spectra. The biological activity of cis-and trans-dibromide was investigated in terms of antibiotic and toxic effects at cellular level using microbiologic and cytogenetic test, respectively. The antimicrobial activity of trans-dibromide9 and cis-dibromide10 was tested against Bacillus spizizenii ATCC 6633, Salmonella typhimurium ATCC 14028,Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 9027. Peripheral blood lymphocytes culture assay was used for determining the cytotoxicity of trans-dibromide 9 and cis-dibromide 10 substrates. Cis-and trans-dibromide showed antibiotic activity and the toxic effects of cis-and transdibromide were measured at cellular level by mitotic index as the cell kinetic parameter in a peripheral lymphocyte culture assay.