In the current investigation, some newer triazines merged benzothiazole hybrids were subjected to molecular properties prediction, drug-likeness, lipophilicity and solubility parameters determination using Molinspiration, Molsoft and ALOGPS 2.1 softwares. Amongst ten proposed analogues only seven therapeutic candidates were chosen on the basis of Lipinski’s “Rule of Five”. Selected title compounds were synthesized by cyclizing 3-chloroaniline and potassium thiocyanate in presence of bromine yielded the corresponding 2-amino benzothiazole synthon, which on further treatment with different substituted aromatic aldehydes afforded Schiff's bases. The later one condensed with phenyl isothiocyanate gave triazine merged benzothiazole analogues (4a-4j). The structural confirmation of the target compounds were established on the basis of IR, 1HNMR and Mass spectral analysis and subjected to in-vitro anti-inflammatory and anti-oxidant screening. Compound 4c and 4g showed pronounced antioxidant and ant-inflammatory activity respectively. The phenyl ring of triazine bearing –OH and –OCH exhibited good biological activity and their predicted drug-likeness model score also found to be convincing among the series.