Copper fluorapatite assisted synthesis of new 1, 2, 3-triazoles bearing a benzothiazolyl moiety and their antibacterial and anticancer activities. (2nd May 2019)

• Record Type: Journal Article
• Authors: Dhumal, Sambhaji T.; Deshmukh, Amarsinh R.; Kharat, Kiran R.; Sathe, Bhaskar R.; Chavan, Santosh S.; Mane, Ramrao A.
• Is Part Of: New journal of chemistry. Volume 43:Number 20(2019)
• Page Start: 7663
• Page End: 7673
• Publication Date: 2019-05-02
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c9nj00377k
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : New 1, 2, 3-triazoles with a benzothiazolyl scaffold have been synthesized for the first time using copper fluorapatite as a catalyst and their antibacterial and anticancer activities are reported. Abstract : A series of new 2-(4-((1-phenyl-1 H -1, 2, 3-triazol-4-yl)methoxy)phenyl)benzo[ d ]thiazoles and 2-(4-((4-(benzo[ d ]thiazol-2-yl)phenoxy)methyl)-1 H -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, 1 H NMR, 13 C NMR and HRMS analyses. All the synthesized compounds were found to be effective against human breast carcinoma (MCF-7) cells. Among them, compounds5e, 5h, 5j, 5o and5p 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, compounds5a, 5c, 5d, 5e, 5f, 5k, 5n, 5o and5q 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.