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Croatica Chemica Acta, Vol. 89 No. 1, 2016.

Original scientific paper

https://doi.org/10.5562/cca2811

Synthesis and Antimicrobial Activity of Furochromone, Benzofuran and Furocoumarin Derivatives Bearing Sulfonyl Moiety

Sadia A. Hessein ; Chemistry Department, Faculty of Science, Al-Azhar University (Girls), Nasr City, Cairo, Egypt
Marwa A. M. Sh. El-Sharief ; Applied Organic Chemistry Department, National Research Centre, Cairo, Egypt
Samir Y. Abbas orcid id orcid.org/0000-0001-7584-5030 ; Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, Egypt
Hamdy Kh. Thabet ; Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Yousry A. Ammar ; Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt

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Abstract

New visnagin-9-sulfonamide derivatives 3 and 4a−c were synthesized through the reaction of visnagin-9-sulfonyl chloride 2 with amino compounds. Acetylation of compounds 4b and 4c gave the monoacetyl and diacetyl derivatives 5 and 6, respectively. Diazotization reaction of compound 4b afforded the corresponding benzotriazole derivative 8. Pyrazole and thiopyrimidine derivatives 9 and 10 were obtained via the opening of pyrone ring upon reaction of compound 3 with hydrazine hydrate and thiourea, respectively. In addition, hydrolysis of compound 3 with potassium hydroxide furnished the visnaginone derivative 11 which used as starting material for synthesize benzofuran derivatives 12−14 and bergaptene derivatives 15−17. The synthesized compounds were tested for antimicrobial activity. Furochromone derivatives 3, 4a−c, 5, 6 and 8 (visnagin-9-sulfonamide derivatives) demonstrate moderate antibacterial and antifungal activities compared with the antibacterial and antifungal activites of the standard drugs. Benzofuran derivatives 11−14 (visnaginone derivatives) showed the lowest antimicrobial activity among all the compounds investigated in this study. Furocoumarin derivatives 15a,b, 16 and 17 (furobenzopyransulfonamide [bergaptensulfonamides]) are moderately active against all the tested strains.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

visnagine (furochromones); visnaginone (benzofurans); bergaptene (furocoumarins); sulfonamides; antimicrobial activity

Hrčak ID:

158795

URI

https://hrcak.srce.hr/158795

Publication date:

20.6.2016.

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