Synthesis and Antioxidant Activity of New Norcantharidin Analogs

• Published in: Chemistry & biodiversity Vol. 16; no. 4; pp. e1800673 - n/a
• Main Authors: Pachuta‐Stec, Anna, Nowak, Renata, Pietrzak, Wioleta, Pitucha, Monika
• Format: Journal Article
• Language: English
• Published: Switzerland Wiley Subscription Services, Inc 01.04.2019
• Subjects: Acidic oxides; Analogs; antioxidant activity; Antioxidants; Biological activity; cyclization reaction; Derivatives; Dicarboxylic acids; Dicarboxylic anhydride; Heptanes; heterocycles; NMR; Norcantharidin; norcantharidin analogs; Nuclear magnetic resonance; structure–activity relationship; Triazoles; Vitamin E; cyclization reaction; biological activity; heterocycles; antioxidant activity; norcantharidin analogs; structure-activity relationship
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.201800673

New norcantharidin analogs were designed and obtained as compounds with biological activity. As a starting material, exo‐7‐oxabicyclo[2.2.1]heptane‐2,3‐dicarboxylic acid anhydride was used. Three groups of compounds: dicarboximides, triazoles and thiazolidines were obtained in multistep reactions. The 1H‐ and 13C‐NMR spectra were used to confirm the structures of all obtained products and they were in agreement with the proposed structure of substances. All derivatives were screened for their antioxidant activity. The most promising group was dicarboximides (1–4, 6). Derivatives 2–4 displayed antioxidant activity with EC50=7.75–10.89 μg/ml, which may be comparable to strong antioxidant Trolox (EC50=6.13 μg/ml). Excellent activity with EC50=10.75 μg/ml also presented norcantharidin analog with 1,2,4‐triazole system (12).