Synthesis Approaches to (-)-Cytoxazone, a Novel Cytokine Modulator, and Related Structures.
(-)-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.
Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, Brazil. izabelmirandaqui@gmail.com.
Izabel L
IL
Miranda
Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, Brazil. italakariny@hotmail.com.
Ítala K B
ÍK
Lopes
Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Viçosa, Viçosa 36570-000, Brazil. marisanogueira@ufv.br.
Marisa A N
MA
Diaz
Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, Brazil. gaspardm@qui.ufmg.br.
Gaspar
G
Diaz
D000818:Animals; D016207:Cytokines / Q000378:metabolism*; D006801:Humans; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015398:Signal Transduction / Q000187:drug effects*; D018418:Th2 Cells / Q000378:metabolism*
D016207:Cytokines; D010080:Oxazoles; C117832:cytoxazone
(−)-cytoxazone; antimicrobial activities; biological activity; cytokine modulator; organic synthesis; stereoselective synthesis