In the present investigation, a series of novel benzothiazole trithiocarbamates have been synthesized. It deals with the design and calculation of Molecular Properties, Drug likeness, Lipophilicity and solubility parameters using Molinspiration, Molsoft softwares. Toxicity parameters were calculated using Osiris software. All the compounds are non-toxic, fulfill the solubility requirements and passing oral bioavailiability criteria. The compounds were synthesized and characterized by IR, 1HNMR, Mass spectral analysis followed by antimicrobial screening. Most of the synthesised compounds (4a-4g) were found to be on conformity with Lipinski’s “Rule of Five” and other parameters, for their onward screening for antimicrobial activity as oral active drugs.