Synthesis and medicinal chemistry of tetronamides: Promising agrochemicals and antitumoral compounds. (1st August 2022)

• Record Type: Journal Article
• Authors: Silva, Júnio G.; de Miranda, Amanda S.; Ismail, Fyaz M.D.; Barbosa, Luiz C.A.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 67(2022)
• Publication Date: 2022-08-01
• Subjects: Basidalin -- Sivanto -- Nicotinic insecticide -- Butenolide -- Podophyllotoxin -- 4-aminofuran-2(5H)-ones; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2022.116815
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Highlights: The tetronamide core is present in compounds displaying varied bioactivities. The reactivity of tetronamides allows their functionalization, providing chemical diversity. This review covers syntheses and functionalization of the tetronamide core. Structure-activity relationship of some tetronamides is discussed herein. Tetronamides include the insecticide sivanto® and potent antitumoral compounds. Abstract: Butenolides and tetronic acids occupy a prominent position in synthetic chemistry due to their ubiquitous distribution in nature. This has stimulated investigations firstly in the synthesis of such systems and, laterly, the interest has turned to the understanding of the quantum structure of such systems, allowing a deeper understanding of the mechanism and reactivity of this cyclic scaffold. In contrast, tetronamides, which consist of compounds bearing a 4-aminofuran-2(5 H )-one backbone, are relatively rare in nature and synthetic routes to such compounds are poorly explored. This review highlights both the importance of the tetronamide scaffold in medicinal chemistry and the most relevant recondite synthetic strategies for obtaining compounds of this class.