Many potent compounds rich in therapeutic potential have been isolated from marine sponges but they have failed to make it to the clinical trials or rather failed in the clinical trials because of the extreme cytotoxicity they possess. In the present study we have evaluated the biological potential of synthetic analogues of dibromotyrosine where we assume that the analogues designed and synthesized have retained their potency but lost their cytotoxicity. 2-(3, 5-dibromo- 4-hydroxyphenyl) acetamide [analogue 1] and ethyl 2-(3, 5-dibromo-4-hydroxyphenyl) acetate [analogue 2] were tested against bacterial strains DH5α and ER2566 and Candida albicans was taken as fungal counterpart. The antimicrobial activity of both the analogues showed inhibitory effects against both the bacterial strains with ER2566 giving MIC50 value of 31.25μg/ml for analogue 1 and 66.19μg/ml for analogue 2 while MIC50 value of 21.72μg/ml was obtained for analogue 1 and 17.69μg/ml for analogue 2 against DH5α.The analogues were also antifungal against Candida albicans with MIC50 values of 170.50μg/ml for analogue 1 and 145.37μg/ml for analogue 2.Subsequent to the wet lab analysis both the analogues proved to be equally effective when subjected to in silico studies using online softwares and docking tools and showed no toxicity against extracted lymphocytes from rat’s blood thereby emphasizing, hopefully correct synthesis of analogues who have probably lost their activity to be cytotoxic.