Publication Type Journal Article
Title Novel Sulfenamides as Promising Acetylcholinesterase Inhibitors
Authors Carla Proenca Maria L. Serralheiro M. Eduarda Araújo Teresa Pamplona Susana Santos M. Soledade C. S. Santos Fatima Frazao
Groups HC MET
Journal JOURNAL OF HETEROCYCLIC CHEMISTRY
Year 2011
Month November
Volume 48
Number 6
Pages 1287-1294
Abstract Several sulfenamide derivatives were designed as possible acetylcholinesterase (AChE) inhibitors. New sulfenamides were synthesized and proved to be stable under the physiological conditions used in the enzymatic assays. N-benzyl-2-benzoxazolylsulfenamide (8) and N-benzyl-2-benzimidazolylsulfenamide (9) revealed anti-AChE activity with IC50 values of 0.6 and 0.8 mu M, respectively, values of the same magnitude as those reported for galantamine and tacrine. The affinity for the biological site was evaluated in terms of interaction/partition toward sodium dodecyl sulfate (SDS) micelles. The inhibitory activity profiles were reasoned in terms of both partition toward a hydrophobic anionic environment and molecular geometry. The X-CSN dihedral angle deviations from collinearity stood out as a major parameter linked to enzyme specificity.
DOI http://dx.doi.org/10.1002/jhet.752
ISBN
Publisher
Book Title
ISSN 0022-152X
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Conference Name
Bibtex ID ISI:000297748100011
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