Finding safer, more powerful and more effective molecules is urgently needed given the rising threat of infectious diseases. Benzoimidazothiazole are a novel class of small molecules that have not been studied on a variety of pharmacological targets. In this report, we discussed novel dihydrobenzo-imidazothiazole scaffold as promising anti-infective agents. Commercially available 1,3-cyclohexane-diones (1a–h) were brominated before being condensed with thiourea to produce 2-amino-5,6-dihydrobenzo[d]thiazol-7(4H)-ones (3a–h) in excellent yields. Compounds 3a-h were cyclized with 2‑bromo-1-(5-chlorothiophen-2-yl)ethan-1-one (4) to produce 2-(5-chlorothiophen-2-yl)-6,7-dihydrobenzo[d]Imidazo [2,1-b]thiazol-8(5H)-ones (5a-h). When synthetic analogues 3a-h and 5a-h were examined for biological activity, they showed effective inhibition against the tested antiviral and antibacterial strains. Two analogues, 3h (CC50: >300 µM, IC50= 8.3 µM, SI = >36) and 5h (CC50: >300 µM, IC50= 4.1 µM, SI = >73) had high levels of virus-inhibiting action when tested against the pandemic influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells with favorable toxicity profile. Among the substances tested against bacterial strains, 3d inhibited Typhi, Subtills, and Mutans bacteria with MICs of 0.78 µM and E. coli with MICs of 1.56 µM against standard streptomycin (MIC:1.56 µM). The novel analogues' physiochemical and molecular docking tests revealed promising pharmacological profiles for further structural optimization and drug development.