Abstract
The design, synthesis and calcimimetic properties of various cyclic sulfonamides and sulfamates are described. The latter were prepared from the corresponding o-alkenylarenesulfonamides via copper- or rhodium-catalyzed intramolecular aziridination. The size of the cyclic sulfonamide rings as well as the position of the crucial (R)-naphthylethylamine substituent significantly affected calcimimetic activity. The most active compounds were the six- and seven-membered sulfonamides 30a and 31a and sulfamate 34a.
Copyright © 2010 Elsevier Ltd. All rights reserved.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Animals
-
Calcimimetic Agents / chemical synthesis*
-
Calcimimetic Agents / chemistry
-
Calcimimetic Agents / pharmacology
-
Catalysis
-
Copper / chemistry
-
Crystallography, X-Ray
-
Cyclization
-
Drug Design
-
Humans
-
Molecular Conformation
-
Mutation
-
Rats
-
Receptors, Calcium-Sensing / agonists*
-
Receptors, Calcium-Sensing / genetics
-
Receptors, Calcium-Sensing / metabolism
-
Rhodium / chemistry
-
Stereoisomerism
-
Structure-Activity Relationship
-
Sulfonamides / chemical synthesis
-
Sulfonamides / chemistry*
-
Sulfonamides / pharmacology
-
Sulfonic Acids / chemical synthesis
-
Sulfonic Acids / chemistry*
-
Sulfonic Acids / pharmacology
Substances
-
Calcimimetic Agents
-
Receptors, Calcium-Sensing
-
Sulfonamides
-
Sulfonic Acids
-
Copper
-
sulfamic acid
-
Rhodium