Synthesis and physicochemical properties of sulfamate derivatives as topical antiglaucoma agents

Several imidazolylphenyl sulfamate and (imidazolylphenoxy)alkyl sulfamate derivatives were synthesized and evaluated as topically active carbonic anhydrase inhibitors. Water solubility, pKa, carbonic anhydrase inhibition, and partition coefficient for the compounds were measured. Sulfamic acid 2-[4-...

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Veröffentlicht in:	Journal of medicinal chemistry 1992-12, Vol.35 (26), p.4790-4794
Hauptverfasser:	LO, Y. S, NOLAN, J. C, MAREN, T. H, WELSTEAD, W. J, GRIPSHOVER, D. F, SHAMBLEE, D. A
Format:	Artikel
Sprache:	eng
Schlagworte:	Administration, Topical Animals Carbonic Anhydrase Inhibitors - chemical synthesis Carbonic Anhydrase Inhibitors - chemistry Carbonic Anhydrase Inhibitors - therapeutic use Chemistry Exact sciences and technology Glaucoma - drug therapy Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Imidazoles - chemical synthesis Imidazoles - chemistry Imidazoles - therapeutic use Intraocular Pressure - drug effects Organic chemistry Preparations and properties Rabbits Structure-Activity Relationship Sulfonic Acids - chemical synthesis Sulfonic Acids - chemistry Sulfonic Acids - pharmacology
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Zusammenfassung:	Several imidazolylphenyl sulfamate and (imidazolylphenoxy)alkyl sulfamate derivatives were synthesized and evaluated as topically active carbonic anhydrase inhibitors. Water solubility, pKa, carbonic anhydrase inhibition, and partition coefficient for the compounds were measured. Sulfamic acid 2-[4-(1H-imidazol-1-yl)phenoxy]ethyl ester monohydrochloride (16) has the best combination of properties and showed excellent topical activity in lowering the intraocular pressure in New Zealand white rabbits.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00104a003