ABSTRACT. A novel series of benzothiazolopyridine derivatives was synthesized via interaction of -2-(benzothiazol-2-yl)-3-(4-chlorophenyl)acrylonitrile (2) with a diverse of commercially available reagents (indandione, thiobarbituric acid, and malononitrile). Moreover, a novel group of benzothiazole linked substituted 1,2,3-triazole derivatives were synthesized by exploring the chemical behavior of 5-benzothiazolyl-2-(4-chlorophenyl)-triazol-4-amine through refluxing in glacial acetic acid,

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... ensation with phthalic anhydride, and cyanoacetylation reactions. All newly synthetized compounds have been tested for their antioxidant and antibacterial activities compared with ascorbic acid and Ampicillin as reference drugs, respectively. The benzothiazolo- pyridopyrimidine compound 6 was found the most potent antioxidant agent with IC50 = 0.015 mg/mL compared to the results of ascorbic acid (IC50 = 0.022 mg/mL). The investigated compounds showed no antibacterial properties against Gram-negative bacterial species, Pseudomonas aeruginosa and Escherichia coli. Benzothiazolopyridine derivative 5 displayed the best growth inhibition against Gram-positive bacteria, Staphylococcus aureus and Bacillus cereus with inhibition zones 24 and 20 mm, respectively. KEY WORDS: Benzothiazole, Pyridobenzothiazole, 1,2,3-Triazole, Naphtharidine, Antioxidant Bull. Chem. Soc. Ethiop. 2022, 36(2), 451-463. DOI: https://dx.doi.org/10.4314/bcse.v36i2.17