Synthesis and Anti-Inflammatory Activity of Novel 2-N-Alkyl Sulfonamide Substituted Derivatives of N-Phenyl Anthranilic Acid

Anthranilic acid class of NSAIDs is the result of the application of classical medicinal chemistry bioisosteric drug design concepts since these derivatives are Nitrogen isosteres of Salicylic acid. N-substituted anthranilic acids have found application in widely varying therapeutics areas including anti-inflammatory, analgesic, antipyretics, diuretics, antifibrinolytic, antimicrobial, anticancer activity. In view of these pharmacological observations of N-substituted anthranilic acid derivatives, it was thought worthwhile to synthesize some new N-substituted anthranilic acid derivatives by incorporating (substituted) benzyl and sulphonyl moieties, at the amino group of the anthranilic acid with the hope to get better anti-inflammatory and analgesic molecules.

Present research work deals with the substitution of N-alkyl sulfonamide group and iodine on 2^nd and 7^th positions of acridone nucleus respectively, to give improved antimicrobial activity. The Ullmann reaction is used for their synthesis, which is based on the reaction of o-halobenzoic acid with arylamines in n-aryl alcohol medium in the presence of potassium carbonate and copper powder. Ullmann reaction synthesizes substituted N-phenyl anthranilic acid. All the derivatives tested showed a moderate spectrum of anti-inflammatory. Thus it is possible that substitution at position 2 of the anthranilic acid by sulfonamidophenyl and modification on the sulfonamide moiety by using various amines and substituting iodine on 5^th position may yield compounds of much improved activity.