ABSTRACT
A common, divergent, efficient, and stereoselective approach to the total syntheses of four carbasugars, namely, (-)-zeylenol, (+)-6-O-benzoylzeylenol, (+)-uvarigranol E and (+)-uvarigranol F from d-mannose derived key intermediate 14 is described. This intermediate was synthesized using mixed aldol condensation, Grignard reaction and ring closing metathesis as key steps by our previous method in nine steps from d-mannose. From this intermediate, we achieved the syntheses of (+)-6-O-benzoylzeylenol, (+)-uvarigranol F in three steps, (+)-uvarigranol E in four steps and improved synthesis of (-)-zeylenol.
Subject(s)
CyclohexenesABSTRACT
In this study, we report the synthesis of novel oxazolidinone derivatives derived from linezolid 3 having p-methoxyphenyl group at C-4 position. In vitro evaluation for their anticancer activity toward cultured A549, DU145, HELA, and MCF7 were carried out. The series of compounds prepared displayed wide range of cytotoxicity in MTT assays (10-70 µM) across the cell lines tested. Of the all tested compounds 16 and 17 displayed good anticancer potential against A549 (lung) and DU145 (prostate) cancer cells. Further, to determine their anticancer potential, in the present study we have assessed effect of 17 on DU145 cells growth in in vitro assays. The results clearly demonstrated that the exposure of DU145 cells to 17 inhibits cell proliferation and induces apoptosis by activation of caspase-3 and -9. Long term exposure of DU145 cells to 17 induced cellular senescence confirmed by senescence marker ß-galactosidase staining of cells on post exposure to 17. The results from this current report support that the oxazolidinone derivatives with ethyl and acryl substitutions showed promising anticancer activity which will be helpful to develop further novel anticancer agents with better therapeutic potential.
