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Reversal of diastereoselectivity in the synthesis of peptidomimetic 3-carboxamide-1,4-benzodiazepin-5-ones.
- Source :
-
Organic letters [Org Lett] 2015 Feb 06; Vol. 17 (3), pp. 612-5. Date of Electronic Publication: 2015 Jan 21. - Publication Year :
- 2015
-
Abstract
- Enantiopure 3-carboxamide-1,4-benzodiazepin-5-ones were synthesized via the Ugi reaction followed by the Staudinger/aza-Wittig or reduction reactions in only two steps. A complete reversal of diastereoselectivity was achieved depending on the cyclization methodology employed. The different orientation of the C3 substituent in our 3-substituted 1,4-benzodiazepin-5-ones with respect to the most studied 1,4-benzodiazepin-2-ones makes them complementary in the development of new drugs because the primary source of binding selectivity of 1,4-benzodiazepines is the selective recognition of ligand conformations by the receptor.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 17
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 25607886
- Full Text :
- https://doi.org/10.1021/ol503628r