A practical synthesis of (S) 3-tert-butoxycarbonylamino-2-oxo-2,3,4,5-tetrahydro-1,5-benzodiazepine-1-acetic acid methyl ester as a conformationally restricted dipeptido-mimetic for caspase-1 (ICE) inhibitors

Bioorganic & Medicinal Chemistry Letters
David J Lauffer, Michael D Mullican

Abstract

A simple and versatile method for the synthesis of (S) 3-tert-butoxycarbonylamino-2-oxo-2,3,4,5-tetrahydro-1,5-benzodiazepine-1-acetic acid methyl ester (4), a dipeptide mimetic, has been developed. The regioselective functionalization of the N1 and N5 ring nitrogens and the C3 amino group is demonstrated in the synthesis of an interleukin-1beta converting enzyme inhibitor 13.

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Citations

Apr 25, 2013·Journal of Medicinal Chemistry·Roberta EttariPaola Conti
Jan 21, 2014·Annales pharmaceutiques françaises·D V Narayana RaoL K Ravindranath
Jun 16, 2009·Medicinal Research Reviews·Roberta EttariNicola Micale
Nov 10, 2015·Chemical Reviews·Marcin PorebaMarcin Drag
Feb 22, 2008·Bioorganic & Medicinal Chemistry Letters·Scott B HoytWilliam H Parsons
Oct 25, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Nuria A Illán-CabezaMiguel N Moreno-Carretero
Dec 17, 2014·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Charity Wayua, Philip S Low
Feb 1, 2008·Journal of Medicinal Chemistry·Roberta EttariMaria Zappalà

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