Oxathiazole-2-one derivative of bortezomib: Synthesis, stability and proteasome inhibition activity


Journal Article

Oxathiazole-2-one is a new candidate for proteasome inhibition which has not been widely explored. We describe herein the synthesis and characterization of a new oxathiazole-2-one derived from the dipeptide backbone of Bortezomib. We found that this new oxathiazole-2-one compound 1 is modestly active against the human 20S proteasome, but surprisingly has no significant activity against the M. tuberculosis proteasome. Additionally, the compound has improved aqueous stability compared to previously reported oxathiazole-2-one compounds. Molecular docking analyses provided information on the structural basis of the observed disparity between the human and mycobacterium proteasomes inhibitory activity of compound 1. © 2011 The Royal Society of Chemistry.

Full Text

Duke Authors

Cited Authors

  • Gryder, BE; Guerrant, W; Chen, CH; Oyelere, AK

Published Date

  • November 1, 2011

Published In

Volume / Issue

  • 2 / 11

Start / End Page

  • 1083 - 1086

Electronic International Standard Serial Number (EISSN)

  • 2040-2511

International Standard Serial Number (ISSN)

  • 2040-2503

Digital Object Identifier (DOI)

  • 10.1039/c1md00208b

Citation Source

  • Scopus