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Issue 20, 2019
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Copper fluorapatite assisted synthesis of new 1,2,3-triazoles bearing a benzothiazolyl moiety and their antibacterial and anticancer activities

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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.

Graphical abstract: Copper fluorapatite assisted synthesis of new 1,2,3-triazoles bearing a benzothiazolyl moiety and their antibacterial and anticancer activities

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Publication details

The article was received on 22 Jan 2019, accepted on 08 Apr 2019 and first published on 09 Apr 2019


Article type: Paper
DOI: 10.1039/C9NJ00377K
New J. Chem., 2019,43, 7663-7673

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

    S. T. Dhumal, A. R. Deshmukh, K. R. Kharat, B. R. Sathe, S. S. Chavan and R. A. Mane, New J. Chem., 2019, 43, 7663
    DOI: 10.1039/C9NJ00377K

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