Magnetic sulfonated polysaccharides as efficient catalysts for synthesis of isoxazole-5-one derivatives possessing a substituted pyrrole ring, as anti-cancer agents

• Published in: RSC advances Vol. 11; no. 58; pp. 36958 - 36964
• Main Authors: Ghasemi, Zarrin, Amale, Afsaneh Hamidian, Azizi, Sajjad, Valizadeh, Sepideh, Soleymani, Jafar
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 17.11.2021; The Royal Society of Chemistry
• Subjects: Anticancer properties; Cancer; Catalysts; Chemical synthesis; Chemistry; Chitosan; Colon; Esters; Iron oxides; Pectin; Polysaccharides; Substitutes
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/d1ra06472j

Four polysaccharides (chitosan, cellulose, starch, and pectin) were magnetized with magnetic iron oxide (Fe 3 O 4 ) and then sulfonated (except pectin) with chlorosulfonic acid. The obtained solid acids were used as a catalyst in three-component reactions between N -substituted-2-formylpyrrole, hydroxylamine-hydrochloride, and β-keto esters for the synthesis of 4-(2-pyrrolyl) methylene-isoxazole-5-ones. The optimal catalyst system was selected and studied by IR, SEM, TEM and XRD methods. The diverse isoxazoline derivatives (obtained via a mild and simple approach) were also fully characterized by spectroscopic methods and screened for anti-cancer activities against HT-29 and MCF-7 colon and breast cancer and HEK 293 normal cells. The results revealed interesting anti-cancer activities. Four magnetic polysaccharides containing acidic groups were used as catalysts for the synthesis of 4-(2-pyrrolyl) methylene-isoxazole-5-ones. The products showed anti-cancer activities.