A series of novel benzofuran derivatives were designed and synthesized through a multistep functional group transformation approach which involves Pechmann condensation of resorcinol followed by a sequence of reaction such as base hydrolysis, activation, dehydration and reduction to afford corresponding acid, amide, nitrile and the Boc protected tryptdiamine-O-analogue derivatives 2-5. The newly synthesized compounds are characterized by FTIR, 1HNMR and LC-MS spectral analysis. The synthesized tryptdiamine-O-analogue of benzofuran has skeletal similarity in structure with melatonin and serotonin with only difference in position of hydroxyl group and is found to be a dimer. In-vitro antibacterial and antioxidant studies were carried out for all the synthesized series of compounds 2-5. Compounds 3, 4 and 5 emerge as good antibacterial and DPPH scavenging agents. In correlation to antibacterial activity, compounds 2-5 along with serotonin and melatonin are subjected for molecular docking studies with GlcN-6-P synthase as target protein and showed minimum binding energy with good affinity towards target protein thus, they may be considered as good inhibitors of GlcN-6-P synthase. Additionally, Lipinski’s rule of five parameters and toxicity parameters were evaluated to predict the bioavailability using online server Molinspiration and Osiris property explorer.