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- Title
Synthesis of Novel 5-(N-Boc-N-Benzyl-2-aminoethyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carboxamides and Their Inhibition of Cathepsins B and K.
- Authors
Lukić, Branislav; Grošelj, Uroš; Novinec, Marko; Svete, Jurij
- Abstract
Eight novel 5-(N-Boc-N-benzyl-2-aminoethyl)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidin-3-carboxamides were prepared in three steps from methyl 3-amino-1H-pyrazole-4-carboxylate and methyl 5-(benzyl(tert-butoxycarbonyl)amino)- 3-oxopentanoate. The synthetic procedure comprises cyclocondensation of the above starting compounds, hydrolysis of the ester, and bis(pentafluorophenyl) carbonate (BPC)-mediated amidation. Title carboxamides were tested for inhibition of cathepsins K and B. The N-butylcarboxamide 5a exhibited appreciable inhibition of cathepsin K (IC50 ~ 25 μM), while the strongest inhibition of cathepsin B was achieved with N-(2-picolyl)carboxamide 5c (IC50 ~ 45 μM).
- Subjects
CHEMICAL synthesis; DRUG development; AMINO acids; CARBOXAMIDES; CATHEPSINS
- Publication
Acta Chimica Slovenica, 2017, Vol 64, Issue 4, p782
- ISSN
1318-0207
- Publication type
Article
- DOI
10.17344/acsi.2017.3421