Synthesis Approaches to (-)-Cytoxazone, a Novel Cytokine Modulator, and Related Structures

• Published in: Molecules (Basel, Switzerland) Vol. 21; no. 9; p. 1176
• Main Authors: Miranda, Izabel L, Lopes, Ítala K B, Diaz, Marisa A N, Diaz, Gaspar
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI 06.09.2016; MDPI AG
• Subjects: (−)-cytoxazone; Animals; antimicrobial activities; biological activity; cytokine modulator; Cytokines - metabolism; Humans; organic synthesis; Oxazoles - chemical synthesis; Oxazoles - chemistry; Oxazoles - pharmacology; Review; Signal Transduction - drug effects; stereoselective synthesis; Th2 Cells - metabolism; biological activity; organic synthesis; antimicrobial activities; (−)-cytoxazone; stereoselective synthesis; cytokine modulator
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules21091176

(-)-Cytoxazone, originally isolated from cultures of a Streptomyces species has an oxazolidin-2-one 4,5-disubstituted ring. It is known that this natural product presents a cytokine modulator effect through the signaling pathway of Th2 cells (type 2 cytokines), which are involved in the process of growth and differentiation of cells. From this, the interest in the development of research aimed at the total synthesis of this molecule and its analogs has remained high, which can be confirmed by the large number of publications on the topic, more than 30 to date. This review focuses on the various creative methods for the synthesis of (-)-cytoxazone and its congeners. The assessment of the preparation of this oxazolidinone and related structures serves as a treatise on the efforts made in the synthesis of this important class of compound from its first total synthesis in 1999.