Design and Synthesis of Some Substituted 1H‐Pyrazolyl‐oxazolidines or 1H‐Pyrazolyl‐thiazolidines as Anti‐inflammatory‐Antimicrobial Agents
Authors:
- 1 April 2003
- journal article
- research article
- Published by Wiley in Archiv der Pharmazie
- Vol. 336 (2) , 111-118
Abstract
Four series of 1H‐pyrazole derivatives have been synthesized. The first series was synthesized starting with the reaction of 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐1H‐pyrazole‐4‐carboxaldehyde1with L‐serine, L‐cysteine, or L‐penicillamine, followed byN‐protection using (Boc)2O to provide compounds2. The latter compounds could beN‐deprotected by 4N HCl/dioxane to afford the second series3orreactedwith NH4OH in the presence of DCC/HOBt to give the corresponding amides4followed byN‐deprotection giving rise to compounds5. The newly synthesized compounds were evaluated for their anti‐inflammatory‐antimicrobial activities. In addition, the ulcerogenic and acute toxicity profiles were determined. Compound5b(2RS, 4R)‐2‐[3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐1H‐pyrazol‐4‐yl]‐5‐methylthiazolidine‐4‐carboxamide, proved to be the most active anti‐inflammatory‐antimicrobial agent in the present study with a good safety margine and no ulcerogenic effect.Keywords
This publication has 21 references indexed in Scilit:
- Substituent Effects on the Antibacterial Activity of Nitrogen−Carbon-Linked (Azolylphenyl)oxazolidinones with Expanded Activity Against the Fastidious Gram-Negative Organisms Haemophilus influenzae and Moraxella catarrhalisJournal of Medicinal Chemistry, 2000
- The Synthesis and Antiviral Activity of 4-Fluoro-1-β-D-ribofuranosyl-1H-pyrazole-3-carboxamideNucleosides and Nucleotides, 1999
- Antimicrobial and antineoplastic activities of new 4-diazopyrazole derivativesEuropean Journal of Medicinal Chemistry, 1998
- Synthesis of dipeptide 4‐nitroanilides containing non‐proteinogenic amino acidsInternational Journal of Peptide and Protein Research, 1995
- Physicochemical Characterization and Acute Toxicity Evaluation of a Positively-charged Submicron Emulsion VehicleJournal of Pharmacy and Pharmacology, 1994
- 3-(2-(3-Pyridinyl)thiazolidin-4-oyl)indoles, a Novel Series of Platelet Activating Factor AntagonistsJournal of Medicinal Chemistry, 1994
- Antiinflammatory activity of novel indole derivativesEuropean Journal of Medicinal Chemistry, 1994
- 1,3,4-Oxadiazole, 1,3,4-thiadiazole, and 1,2,4-triazole analogs of the fenamates: in vitro inhibition of cyclooxygenase and 5-lipoxygenase activitiesJournal of Medicinal Chemistry, 1993
- 2R,4S-2-(2′-Methyl-3′-hydroxy-5′-hydroxymethylenepyridine-C4′)-5,5-dimethylthiazolidine-4-carboxylic acid, the product of the reaction of D-penicillamine and vitamin B6Canadian Journal of Chemistry, 1991
- Synthesis and anti-microbial evaluation of 2-methyl-3-substituted-4(3H)-quinazolinonesEuropean Journal of Medicinal Chemistry, 1987