Synthesis and anti-inflammatory, analgesic, and antipyretic activities of N-[β-(p-substituted benzoyl)ethyl]amino acids

Abstract

Alkylation of a number of a-amino acids, as well as b-phenyl-b-alanine and g-aminobutyric acid, with the hydrochlorides of p-substituted b-diethylaminopropiophenones resulted in the synthesis of N-[b-(p-substituted benzoyl)ethyl]cysteine, threonine, methionine, isoleucine, asparagine, and glutamine, along with b-phenyl-b-alanine, and g-aminobutyric acid. The anti-inflammatory activities of the resulting compounds were studied; several of them had moderate anti-inflammatory activity.

Mannich bases in medicinal chemistry and drug design

“…At the same dose, these two candidates 254 also showed 88% and 79%, respectively, of the activity of reference drug indomethacin (dose of 3 mg/kg) on chronic inflammation. A continuation of this study was undertaken with a view to broaden the nature of amino acids (cysteine, threonine, methionine, isoleucine, asparagine, and glutamine) as amine moieties in Mannich bases 254, and also the nature of the alkoxy substituents in the aromatic ring, but these novel candidates had no anti-inflammatory activity at 5 mg/kg, with the exception of two candidates 254 (R ¼ OC 2 H 5 ; R 1 ¼ CH 2 SH, CH 2 CONH 2 ), which displayed mild activity in the acute inflammation model [395].…”

Current Drifts in Design and Development of Prodrugs

“…Most of the acidic and basic amino acids are also used in designing of mutual prodrugs like glutamic acid, glutamine, tryptophan, alanine, phenylalanine and cysteine. These amino acids synergise the anti-inflammatory and analgesic property of conjugated NSAIDs and some of them have potential antioxidant and hepatoprotective property (18)(19)(20)(21). Glutamine have potential to reduce or prevent the liver damage occurred by hepatic inflow occlusion (22).…”