799262-24-1

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 5651-86-5 4-(prop-2-ynyloxy)benzaldehyde 
• 6265-55-0 2-(4-hydroxyphenyl)benzothiazole 
• 106-96-7 propargyl bromide 
• 137-07-5 2-amino-benzenethiol 

Relevant academic research and scientific papers

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

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.

2-Arylation/alkylation of benzothiazoles using superparamagneticgraphene oxide-Fe3O4 hybrid material as a heterogeneous catalystwith diisopropyl azodicarboxylate (DIAD) as an oxidant

In this report, we introduced Graphene oxide-iron oxide (GO-Fe3O4) nanocomposites as a heterogeneous catalyst for arylation/alkylation of benzothiazoles with aldehydes and benzylic alcohols in the presence of diisopropyl azodicarboxylate (DIAD) as an oxidant which exclusively produced 2-aryl (alkyl)-1H–benzothizoles in moderate to excellent yields. The absence of precious metals and toxic solvent, easy product isolation, and recyclability of the GO-Fe3O4 with no loss of activity are notable advantages of this method.

Synthesis of novel benzimidazole and benzothiazole derivatives bearing a 1,2,3-triazole ring system and their acetylcholinesterase inhibitory activity

A series of 20 novel benzimidazole and benzothiazole derivatives linked to a 1,2,3-triazole ring system was synthesised, characterised and evaluated for in vitro acetylcholinesterase (AChE) inhibitory activity. Several copper catalysts and solvents were screened to establish the optimal conditions for the preparation of the target compounds. Three different linkers were used to optimise the enzyme inhibitory effect. Out of the 20 compounds, 13 showed some AChE inhibition. The most potent compound, which showed 84% inhibition at 100 μM, contained a 1-(2-fluorobenzyl)-1,2,3-triazole linked to a benzimidazole group. A docking simulation study showed that the most active compound bound preferentially to the catalytic anionic subsite of the AChE enzyme.

One-pot synthesis of 2-arylbenzimidazole, 2-arylbenzothiazole and 2-arylbenzoxazole derivatives using vanadium(IV)-salen complex as homogeneous catalyst and vanadium(IV)-salen complex nanoparticles immobilized onto silica as a heterogeneous nanocatalyst

The efficient synthesis of 2-arylbenzimidazole, 2-arylbenzothiazole and 2-arylbenzoxazole derivatives is described by condensation of aryl aldehydes and o-phenylenediamines, 2-aminothiophenol and 2-aminophenol in a single pot using a catalytic amount of vanadium(IV)-salen complex or vanadium-salen nanoparticles supported on silica (5.0 mol%) in excellent isolated yields. The immobilized catalyst was characterized by powder X-ray diffraction, scanning electron microscopy, atomic force microscopy, transmission electron microscopy, inductively coupled plasma analysis, thermogravimetric instrument for analysis of nitrogen adsorption and FT-IR spectroscopy.