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A series of fifteen novel gallic acid esters (7a-o) was synthesized and structure was confirmed by spectral data. Antibiotic power of compounds was assessed against a panel of ten microbes while antioxidant activity was gauged by employing DPPH, ABTS and antilipid peroxidation assays. It was found that in comparison to lead, many of the synthesized derivatives implied much improved broad spectrum antimicrobial effect. Most effective compound found was 7c specifically against resistant gram-negative strains such as P. aeruginosa, E. coli and E. aerogenes. Potent antioxidant capacity was exhibited by7a and 7d in electron transfer assays while 7j and 7c provided maximum shielding against lipid peroxidation. Structure-activity analysis revealed that analogues with electron -withdrawing substituent particularly chloro group stand out as much better antibiotic agent. This study suggests that halogenated gallic acid analogues might be promising pharmacological candidates in view of further drug development. This work is licensed under a Creative Commons Attribution 4.0 International License.