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Stereoselective synthesis of functionalized pyroglutamates |
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| Authors: | Matthew J. Just Srinivas TekkamMohammad A. Alam Subash C. JonnalagaddaJoseph L. Johnson Venkatram R. Mereddy |
| Affiliation: | a Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA b Department of Chemistry and Biochemistry, Rowan University, Glassboro, NJ 08028, USA c Department of Pharmacy Practice and Pharmaceutical Sciences, College of Pharmacy, University of Minnesota, Duluth, MN 55812, USA |
| Abstract: | Novel stereoselective synthesis of α-methylene-β-substituted pyroglutamates, and α-alkylidene-pyroglutamates has been achieved via substrate controlled asymmetric alkylation of l-threonine derived oxazole with Baylis-Hillman reaction based allyl bromides and acetates, respectively. The synthesized compounds were evaluated for their proteasome inhibition and cytotoxicity on multiple myeloma cells. |
| Keywords: | Pyroglutamates (γ-carboxy-γ-lactams) Threonine Oxazoles Substrate controlled alkylation Baylis-Hillman bromides/acetates |
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