Rapid Microwave‐Promoted Synthesis of New Sulfonylmethylbenzothiazoles in Water.

Gellis, Armand; Boufatah, Narimène; Vanelle, Patrice

doi:10.1002/chin.200639147

Cited by 2 publications

(4 citation statements)

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“…Firstly, we tried to prepare 4 according to these literatures, but the yield was not ideal. Then we employed a microwave-assisted procedure developed by Gellis [ 27 ], treating 2-aminobenzenethiol 2 with 2-chloroacetyl chloride in acetic acid under microwave irradiation for 10 min to provide the required intermediate 4 , to our delight, the yield was up to 87%. Compared with the traditional method, the microwave-assisted procedure was environmentally friendly and efficient, with a less time and higher yield.…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of 2-Chloromethyl-benzothiazole ( 4 ) [ 27 ]. To a solution of 2-aminobenzenethiol (1 g, 7.93 mmol) in acetic acid (15 mL), and 2-chloroacetyl chloride (1.35 g, 1.19 mmol) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

“…The combined organic layers were dried over MgSO 4 and concentrated under vacuum. Purification of the residue by column chromatography on silica gel (petroleum ether/acetone, 10:1 v : v ) gave compound 4 as a yellow solid (1.90 g, 86.8%) [ 27 ]. m.p., 89–90 °C; MS (+ESI) m / z 184.02 [M + H] + .…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, Antifungal Activities and Molecular Docking Studies of Benzoxazole and Benzothiazole Derivatives

Luo

Zhang

et al. 2018

Molecules

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Based on benzoxazole and benzothiazole scaffold as an important pharmacophore, two series of 2-(aryloxymethyl) benzoxazole and benzothiazole derivatives were synthesized and their antifungal effects against eight phytopathogenic fungi were evaluated. Compounds 5a, 5b, 5h, and 5i exhibited significant antifungal activities against most of the pathogens tested. Especially 5a, 5b, 5h, 5i, 5j, and 6h inhibited the growth of F. solani with IC50 of 4.34–17.61 μg/mL, which were stronger than that of the positive control, hymexazol (IC50 of 38.92 μg/mL). 5h was the most potent inhibitor (IC50 of 4.34 μg/mL) against F. Solani, which was about nine times more potent than hymexazol. Most of the test compounds displayed significant antifungal effects against B. cinerea (IC50 of 19.92–77.41 μg/mL), among them, 5a was the best one (IC50 of 19.92 μg/mL). The structure-activity relationships (SARs) were compared and analyzed. The result indicates that the electron-drawing ability and position of the substituents have a significant impact on biological activities. Furthermore, docking studies were carried out on the lipid transfer protein sec14p from S. cerevisiae, and preliminarily verified the antifungal activities. Taken together, these results provide 2-(phenoxymethyl)benzo[d]oxazole as an encouraging framework that could lead to the development of potent novel antifungal agents.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis, Antifungal Activities and Molecular Docking Studies of Benzoxazole and Benzothiazole Derivatives

Luo

Zhang

et al. 2018

Molecules

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“…Water has also proven to be an excellent solvent for microwave-promoted synthesis [ 38 , 39 , 40 ]. Furthermore, as well as being energy efficient, microwaves can also enhance reaction rates, and in many cases, improve yields [ 41 , 42 , 43 , 44 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Promising in Vitro Antiproliferative Activity of Sulfones of a 5-Nitrothiazole Series

et al. 2012

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The synthesis in water of new sulfone derivatives under microwave irradiation is described. This eco-friendly process leads to the expected products in good yields by reaction of various substituted sulfinates (commercially available or obtained by reduction of the corresponding sulfonyl chlorides) with 4-chloromethyl-2-methyl-5-nitro-1,3-thiazole. In order to evaluate the antiproliferative effect of these compounds, several sulfone derivatives are also dichlorinated on the Cα next to the sulfonyl group. An evaluation on different cancer cell lines reveals promising selective in vitro antiproliferative activity toward HepG2 human cell lines by dihydrogenated sulfones, suggesting further research should be to explore their anticancer potential in the treatment of liver cancer.

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Rapid Microwave‐Promoted Synthesis of New Sulfonylmethylbenzothiazoles in Water.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 2 publications

References 1 publication

Synthesis, Antifungal Activities and Molecular Docking Studies of Benzoxazole and Benzothiazole Derivatives

Synthesis, Antifungal Activities and Molecular Docking Studies of Benzoxazole and Benzothiazole Derivatives

Synthesis and Promising in Vitro Antiproliferative Activity of Sulfones of a 5-Nitrothiazole Series

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