Synthesis and characterization of 5-bromo-6-(4-chlorophenyl)-2-propylimidazol[2,1-b][1,3,4]thiadiazole: A potential anti-cancer drug

• Main Authors: Ocampo, Charlene Q., Mercado, Jouella Camille Q., Alea, Glenn V., Oyong, Glenn G., Lagua, Faith Marie G.
• Format: text
• Published: Animo Repository 2015
• Subjects: Imidazoles—Synthesis; Antineoplastic agents; Chemistry
• Online Access: https://animorepository.dlsu.edu.ph/faculty_research/11446
• Institution: De La Salle University

An imidazo[2,1-b][1,3,4]thiadiazole derivative, 5-bromo-6-(4-chlorophenyl)-2- propylimidazo[2,1-b][1,3,4]thiadiazole (5) was synthesized and characterized. The synthesis involved the preparation of an acylated thiosemicarbazide derivative (3) via nucleophilic acyl substitution, followed by dehydrocyclization with 2-Bromo-4'-chloroacetophenone to generate the imidazo[2,1- b][1,3,4]thiadiazole ring. This was then brominated to afford the target compound (5) in 76% yield. The identity of the synthesized compounds was confirmed via Mass Spectrometry (ESI-MS). The compound’s potential anticancer activity was assessed with a PrestoBlueTM assay which showed a close cytotoxicity index with the standard anticancer drug (Bleomycin) on human colon adenocarcinoma grade II (HT-29) and human breast adenocarcinoma (MCF-7) cancer cell lines. It was also observed to possess lower toxicity towards normal cells. These results may be used to assess the structure activity relationship (SAR) of other derivatives with different alkyl chain lengths with respect to its anticancer activity.