000059748 001__ 59748
000059748 005__ 20180317092302.0
000059748 022__ $$a0022-3263
000059748 02470 $$2ISI$$a000184060600023
000059748 037__ $$aARTICLE
000059748 245__ $$aSynthesis of enantiomerically pure 1,2-diamine derivatives of 7-azabicyclo[2.2.1]heptane. New leads as glycosidase inhibitors and rigid scaffolds for the preparation of peptide analogues
000059748 260__ $$c2003
000059748 269__ $$a2003
000059748 336__ $$aJournal Articles
000059748 500__ $$aEcole Polytech Fed Lausanne, Inst Chim Mol & Biol, EPFL BCH, CH-1015 Lausanne, Switzerland.
000059748 520__ $$aEnantiomerically pure alcohols (-)- and (+)-7-tert-butoxycarbonyl-6-endo-p-toluenesulfonyl-7azabicyclo[2.2.1]hep t-2-en-5-endo-ol ((-)-11 and (+)-11) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrroel and 2-bromo-1-p-toluenesulfonylacetylene, including a resolution method. These two alcohols were converted into (+)- and (-)-5-exo-amino-7-(tertbutoxycarbonyl))-2,3-exo-isopropylidenedioxy-7-az abicyclo[2.2.1]heptane ((+)-18 and (-)-18) and (+)and (-)-5-endo-amino-7-(tert-butoxycarbonyl)-2,3-exo-isopropylidenedioxy-7-a zabicyclo[2.2.1]heptane ((+)-19 and (-)-19) after adequate fanctionalization and desulfonylation steps. The corresponding conformationally constrained bicyclic 1,2-diamines (+)-4, (-)-4, (+/-)-5, (+/-)-6, (+)-7, and (-)-7 were obtained from the protected precursors 18 and 19 and evaluated as glycosidase inhibitors. Diamines (+)-4, (-)-4, (+)-6, and (-)-6 can be seen as new nonpeptide molecular scaffolds for the design of peptide analogues.
000059748 6531_ $$aDynamic combinatorial chemistry
000059748 6531_ $$aparallel beta-sheets
000059748 6531_ $$aendo-(2s
000059748 6531_ $$a3r)-norborn-5-ene residue
000059748 6531_ $$aconformational-analysis
000059748 6531_ $$amolecular
000059748 6531_ $$ascaffolds
000059748 6531_ $$alocal structures
000059748 6531_ $$aformal synthesis
000059748 6531_ $$aturn inducer
000059748 6531_ $$aamino-acids
000059748 6531_ $$apeptidomimetics
000059748 700__ $$aMoreno-Vargas, A. J.
000059748 700__ $$0241093$$aSchutz, C.$$g148843
000059748 700__ $$0240189$$aScopelliti, R.$$g148592
000059748 700__ $$0240222$$aVogel, P.$$g123681
000059748 773__ $$j68$$k14$$q5632-5640$$tJournal of Organic Chemistry
000059748 909CO $$ooai:infoscience.tind.io:59748$$particle$$pSB
000059748 909C0 $$0252076$$pLGSA$$xU10111
000059748 937__ $$aLGSA-ARTICLE-2003-005
000059748 970__ $$aISI:000184060600023/LGSA
000059748 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000059748 980__ $$aARTICLE