Copper Fluorapatite assisted synthesis of new 1,2,3-triazoles bearing benzothiazolyl moiety and their antibacterial and anticancer activities

Abstract: A series of new 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)benzo[d] thiazoles and 2-(4-((4-(benzo[d]thiazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenylacetamides (5a-t) has been synthesized via Copper Fluorapatite (CuFAP) catalysed click reaction. The compounds (5a-t) were synthesized using freshly prepared 2-aryl-4-hydroxybenzothiazole (1) as a starting material. 2-Aryl-4-hydroxybenzothiazole (1) was condensed with propargyl bromide (2) in N,N-dimethylformamide in the presence of potassium carbonate to obtain a key intermediate, benzothiazolyl phenoxymethylalkyne (3). This alkyne (3) was then separately subjected following click chemistry with freshly prepared aryl/benzyl azides and substituted 2-azido-N-phenylacetamides (4a-t) in presence of Copper fluorapatite (CuFAP) and triethyl amine and obtained better to excellent yields of the titled compounds (5a-t). All the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and HRMS analyses. All the synthesized compounds were found to be effective against human breast carcinoma (MCF-7) cells. Among them, compounds 5e, 5h, 5j, 5o and 5p were found to be strong inhibitors for the growth of MCF-7 cells with IC50 values 10.14, 9.84, 10.06, 10.13 and 9.19 µg/mL, respectively. In addition, compounds 5a, 5c, 5d, 5e, 5f, 5k, 5n, 5o and 5q have shown activity against the multidrug resistant pathogenic strain of E.coli with MIC values 7.99, 8.44, 8.11, 8.06, 8.54, 9.40, 8.02, 9.25 and 10.62 µg/mL, respectively.