Bicyclic carbamates as inhibitors of papain-like cathepsin proteases
…, H Liu, D Mason, B Bursulaya, C Tumanut, J Li…
Index: Epple, Robert; Urbina, Hugo D.; Russo, Ross; Liu, Hong; Mason, Daniel; Bursulaya, Badry; Tumanut, Christine; Li, Jun; Harris, Jennifer L. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 5 p. 1254 - 1259
Full Text: HTML
Citation Number: 7
Abstract
A 6-oxa-1-aza-bicyclo [3.2. 1] octan-7-one system inhibits the proteolytic activity of several cysteine proteases belonging to the papain family. In vitro mechanistic studies and in silico calculations suggest that the minimal π-overlap between the bridgehead nitrogen and the carbonyl leads to a considerable weakening of the urethane system, making it susceptible to nucleophilic attack from the active site thiol group. The resulting covalent adduct is slowly ...
Related Articles:
[Newhouse, Bradley J.; Hansen, Joshua D.; Grina, Jonas; Welch, Mike; Topalov, George; Littman, Nicole; Callejo, Michele; Martinson, Matthew; Galbraith, Sarah; Laird, Ellen R.; Brandhuber, Barbara J.; Vigers, Guy; Morales, Tony; Woessner, Rich; Randolph, Nikole; Lyssikatos, Joseph; Olivero, Alan Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3488 - 3492]
[Newhouse, Bradley J.; Hansen, Joshua D.; Grina, Jonas; Welch, Mike; Topalov, George; Littman, Nicole; Callejo, Michele; Martinson, Matthew; Galbraith, Sarah; Laird, Ellen R.; Brandhuber, Barbara J.; Vigers, Guy; Morales, Tony; Woessner, Rich; Randolph, Nikole; Lyssikatos, Joseph; Olivero, Alan Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3488 - 3492]