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A new series of coloring compounds (pigments) based on 5-(2-aminothiazol-5-yl)thiazol-2-amine and 5-(4-aminophenyl)thiazol-2-amine as heterocyclic alternatives for benzidine based on disazo dyestuffs were synthesized. All the newly synthesized pigments are characterized based on their physical, spectral, and analytical data. The antimicrobial activity showed that introducing the heterocyclic analogues thiazole (mono or  bis ) exhibited less toxic and resisted antimicrobial (five gram-positive strain, three gram-negative, and three fungal species). Thus, derivatives demonstrated moderate to good activity compared with Gentamycin and Ketoconazole. Furthermore, the pigments screened for their  in vitro  antioxidant properties by the DPPH method, and the newly designed pigments  PG4–PG11  with thiazole moiety causes increase antioxidant properties with IC 50  values ranged between (0.054–0.192 µM) compared with  PG1, PG2,  and  PG3 ( IC 50  = 0.712, 0.239, and 0.191 µM) as well as Ascorbic acid (IC 50  = 2.532 µM). Further, the synthesized pigments' cytotoxicity activity evaluated against HepG-2 and showed IC 50  values ranged between (53.52–94.05 µM) compared with  PG1 – PG3  (IC 50  =216.04–393.58 µM) and doxorubicin (IC 50  = 8.17 µM). Molecular docking study concluded that thiazole moiety might be made one or more binding mode as critical hydrogen bonding through the nitrogen of thiazole, as well as arene-cation and/or arene-arene interaction with dihydrofolate reductase (DHFR) active site in 1DLS protein.

polycyclic aromatic compounds

A Novel of Azo-Thiazole Moiety Alternative for Benzidine-Based Pigments: Design, Synthesis, Characterization, Biological Evaluation, and Molecular Docking Study