Copper fluorapatite assisted synthesis of new 1,2,3-triazoles bearing a 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) have been synthesized via a 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 to subsequent click chemistry with freshly prepared aryl/benzyl azides and substituted 2-azido-N-phenylacetamides (4a–t) in the presence of copper fluorapatite (CuFAP) and triethyl amine and good to excellent yields of the title compounds (5a–t) were obtained. 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 of 10.14, 9.84, 10.06, 10.13 and 9.19 μg mL⁻¹, respectively. In addition, compounds 5a, 5c, 5d, 5e, 5f, 5k, 5n, 5o and 5q have shown activity against a multidrug resistant pathogenic strain of E. coli with MIC values of 7.99, 8.44, 8.11, 8.06, 8.54, 9.40, 8.02, 9.25 and 10.62 μg mL⁻¹, respectively.