Paper
Difluoro(sulfinato)methylation of N-sulfinyl imines facilitated by 2-pyridyl sulfone: stereoselective synthesis of difluorinated β-amino sulfonic acids and peptidosulfonamides.
Published Oct 4, 2013 · G. Prakash, C. Ni, F. Wang
Angewandte Chemie
31
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Abstract
Fluorine, despite its almost complete absence from biological systems in nature, has become one of the most utilized element for modulating the properties of biologically active molecules and for studying their mechanism of action. The sulfonamide moiety is one of the most important pharmacophores in medicinal chemistry, and a-fluorosulfonamides have been shown to have improved anti-inflammatory activity and enzyme inhibitory potency. It has been rationalized that a-fluorine substitutions of sulfonamides can increase their acidity and lipophilicity, both of which can significantly affect the biological activity of these molecules. However, biological studies on fluorinated sulfonamides have been largely limited to simple a-fluorosulfonamides with the general structure A. In contrast, b-sulfonamidopeptides, as structural analogues of peptides with enhanced metabolic
Difluorinated -amino sulfonic acids and peptidosulfonamides show potential for improved anti-inflammatory and enzyme inhibitory properties, with potential for further biological studies.
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