Synthesis of 2-(4-sec-butyl-phenyl)-propionic Acid- Pyrrolidin-2-ylcarbamoyl Methyl Ester Derivatives as Anti-inflammatory Potential
نویسندگان
چکیده
Synthesis of 2-(4-sec-butyl-phenyl)-propionic acid-pyrrolidin-2-ylcarbamoyl methyl ester with bio-isosteric concept for ibuprofen with enhancing anti-inflammatory potential. Ibuprofen on refluxing with 2-amino pyridine in chloroacetyl chloride in presence of glacial acetic acid gave 2-(4-sec-butyl-phenyl)-propionic acid-pyrrolidin-2-yl-carbamoyl methyl ester, which can be used as a prodrug for ibuprofen. Derivatives on treatment with (various cycloamino moieties such as morpholine, pyrrolidine, hydrazine hydrate etc.) gave compounds and structures of all these compounds were confirmed on the basis of their analytical and spectral data. The title compounds were characterized by their spectral (I.R., 1H NMR, Mass Spectroscopy) and elemental analysis. Some of these compounds have shown significant anti-inflammatory activity.
منابع مشابه
A Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids
L-Tyrosine and L-Dopa are the precursors in the biological synthesis of amine neurotransmitters. On the other hand, phenylalanine as an aromatic amino acid (AAA) is a precursor in the synthesis of L-Tyrosine and L-Dopa. For some substrates such as amino acids, resolution by the formation of diastereomers offers an attractive alternative. Among different methods in this case, crystallization-ind...
متن کاملSynthesis of 5-phenyl-1-(3-pyridyl)-1H-1,2,4-triazole-3-carboxylic acid derivatives of potential anti-inflammatory activity.
A series of 5-phenyl-1-(3-pyridyl)-1H-1,2,4-triazole-3-carboxylic acid derivatives 4-10 were synthesized by rearrangement of 4-(3-pyridyl)-hydrazono-2-phenyl-2-oxazolin-5-one 3 in the presence of different nucleophiles to afford derivatives 4, 7, and 8, while hydroxamic acid derivative 6 was prepared from reaction of methyl ester 4 with hydroxylamine hydrochloride. Semicarbazide 9 and thiosemic...
متن کاملDevelopment and optimization of the synthesis of new thiazolidin-4-one derivatives of ibuprofen.
UNLABELLED Ibuprofen, an important nonsteroidal anti-inflammatory agent, is one of the most prescribed drugs for the treatment of pain and inflammation from various rheumatic diseases, but some side effects can occur on long-term use. AIM The method for synthesis optimization of new derivatives of Ibuprofen with thiazolidin-4-one moiety, with improved pharmacological and toxicological profile...
متن کاملSynthesis, characterization and antioxidant activity of some new thiazolidin-4-one derivatives.
AIM To design new thiazolidin-4-ones derivatives and to evaluate their potential antioxidant effects using in vitro methods. MATERIAL AND METHODS New ethyl esters of the 2-(R-phenyl)-4-oxo-thiazolidin-3-yl propionic acid were synthesized using "one step reaction" between different aromatic aldehydes, thioglycolic acid and beta-alanine ethyl ester hydrochloride. The antioxidant potential of th...
متن کاملSynthesis and pharmacological evaluation of some 4-oxo-quinoline-2-carboxylic acid derivatives as anti-inflammatory and analgesic agents.
The synthesis and the pharmacological activity of a series of 1-aroyl derivatives of kynurenic acid methyl ester (4-oxo-quinolin-2-carboxy methyl (KYNA) esters), structurally related to NSAID indomethacin are described. The derivatives were screened in vivo for anti-inflammatory and analgesic activities. Most of the compounds exhibited good anti-inflammatory and analgesic activities. An automat...
متن کامل