Synthesis of new 2-([(phenoxy or phenyl)acetyl]amino)benzoic acid derivatives as 3 alpha-hydroxysteroid dehydrogenase inhibitors and potential antiinflammatory agents.
A number of 2-([(phenoxy or phenyl)acetyl]amino)benzoic acid derivatives were prepared in about 50% yield from (phenoxy or phenyl)acetyl chloride and anthranilic acid derivatives. All the compounds were tested as in vitro inhibitors of 3 alpha-hydroxysteroid dehydrogenase, since enzyme inhibition predicts potential antiinflammatory activity in vivo. The most active compounds 3 l, m, s are about 3.5 times more active than acetylsalicylic acid (ASA). Activity is influenced by electronic as well as steric effects.
Daidone
G
G
Dipartimento di Chimica e Technologie Farmaceutiche, Università degli Studi di Palermo, Italy.
Plescia
S
S
Bajardi
M L
ML
Schillaci
D
D
D015096:3-Hydroxysteroid Dehydrogenases / Q000037:antagonists & inhibitors*; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D008826:Microbial Sensitivity Tests; D051381:Rats; D015003:Yeasts / Q000187:drug effects
D062365:Aminobenzoates; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D004791:Enzyme Inhibitors; D015096:3-Hydroxysteroid Dehydrogenases