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Issue 11, 2011
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Oxathiazole-2-one derivative of bortezomib: Synthesis, stability and proteasome inhibition activity

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Abstract

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.

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

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Publication details

The article was received on 12 Aug 2011, accepted on 24 Aug 2011 and first published on 16 Sep 2011


Article type: Concise Article
DOI: 10.1039/C1MD00208B
Citation: Med. Chem. Commun., 2011,2, 1083-1086
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    Oxathiazole-2-one derivative of bortezomib: Synthesis, stability and proteasome inhibition activity

    B. E. Gryder, W. Guerrant, C. H. Chen and A. K. Oyelere, Med. Chem. Commun., 2011, 2, 1083
    DOI: 10.1039/C1MD00208B

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