SYNTHESIS AND BIOLOGICAL ACTIVITIES OF SOME BENZO[d]THIAZOLE DERIVATIVES CONTAINING AN AMIDE BOND

Nine novel benzo[d]thiazole derivatives (E1 – E9) featuring an amide bond were synthesized via an efficient coupling reaction between carboxylic acids and amines using hexafluorophosphate azabenzotriazole tetramethyl uronium (HATU) as the coupling reagent. The reaction was carried out under mild conditions, affording the desired products in high yields (75 – 90%). Structural characterization of the synthesized compounds was achieved using modern spectroscopic techniques, including infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS), which confirmed the formation of the targeted benzo[d]thiazole scaffolds. In addition to the synthetic work, the biological activities of selected compounds were evaluated. Cytotoxic activity was assessed against the carcinoma cell line (KB), revealing that compounds E1, E3, E4, E6, and E7 exhibited moderate inhibitory effects, with IC₅₀ values of 48.29, 115.46, 89.36, 84.09, and 121.89 µg/mL, respectively. However, compounds E6 and E7 did not show significant cytotoxicity against other cancer cell lines such as Hep-G2, A549, and MCF7, nor did they demonstrate noteworthy antioxidant activity. Furthermore, compounds E1, E2, E3, E4, E5, and E8 were inactive against both Gr(+) and Gr(-) bacteria as well as fungal strains. These findings provide valuable insight into the structure – activity relationships of benzo[d]thiazole derivatives and support their potential development as anticancer agents. For citation: Nguyen Duc Du, Pham Huu Dien, Nguyen Thi Thach Thao, Nguyen Thi Ngoc Mai, Nguyen Van Dat, Duong Quoc Hoan Synthesis and biological activities of some benzo[d]thiazole derivatives containing an amide bond. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2025. V. 68. N 10. P. 19-25. DOI: 10.6060/ivkkt.20256810.7227.