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.
Several substituted 2-aminophenylacetic acid derivatives were prepared and tested for in vitro prostaglandin synthetase inhibition activity and for in vivo antiinflammatory activity. The 2-amino substituent is beneficial to potency in the inhibition of prostaglandin synthetase for the 3-phenoxy, 4-phenyl, and 3-benzoyl series, but only the 3-benzoyl series shows increased antiinflammatory potency in the in vivo assay.
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