Romanian Society of Pharmaceutical Sciences
 

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HETEROCYCLES 46. SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF THIAZOLO[3,2-b][1,2,4]TRIAZOLES BEARING BENZENESULFONAMIDE MOIETY

ANAMARIA CRISTINA 1,2, DENISA LEONTE 1, LAURIAN VLASE 3, LÁSZLÓ CSABA BENCZE 4, SILVIA IMRE 5, BOGDAN APAN 6, CRISTINA MOGOȘAN 2, VALENTIN ZAHARIA 1*

1.“Iuliu Haţieganu” University of Medicine and Pharmacy, Department of Organic Chemistry, 41 Victor Babeș Street, 400012, Cluj-Napoca, Romania
2 .“Iuliu Haţieganu” University of Medicine and Pharmacy, Department of Pharmacology, Physiology and Pathophysiology, 6 Louis Pasteur Street, 400349, Cluj-Napoca, Romania
3 .“Iuliu Haţieganu” University of Medicine and Pharmacy, Department of Pharmaceutical Technology and Biopharmaceutics, 41 Victor Babeș Street, 400012, Cluj-Napoca, Romania
4 .“Babeş-Bolyai” University, Faculty of Chemistry and Chemical Engineering, Biocatalysis and Biotransformation Research Group, 11 Arany János Street, 400028, Cluj-Napoca, Romania
5 .University of Medicine and Pharmacy Tîrgu Mureș, Department of Analytical Chemistry and Drug Analysis, 38 Gheorghe Marinescu Street, 540139, Târgu Mureș, Romania
6 .“Iuliu Haţieganu” University of Medicine and Pharmacy, Department of Pharmacology, Toxicology and Clinical Pharmacology, 23 Gheorghe Marinescu Street, 400337, Cluj-Napoca, Romania

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In order to synthesize novel anti-inflammatory and analgesic compounds with reduced ulcerogenic risk, a series of thiazolo[3,2-b][1,2,4]triazoles (6a-6d) and their corresponding acyclic intermediates (5a-5d) bearing benzenesulfonamide moiety were obtained and characterized by spectral analysis (1H NMR, 13C NMR, IR and MS). All synthesized compounds were evaluated in vivo for their anti-inflammatory and antinociceptive activities in a rat model of acute inflammation induced by λ-carrageenan. The compounds 5b, 5c and 6d showed significant anti-inflammatory activity when compared to negative control group, but they did not show superior anti-inflammatory activity when compared to diclofenac, as reference drug. The compounds were also screened for antinociceptive activity in a model of inflammatory hyperalgesia and compounds 5a, 5b, 5c, 6a, 6d presented a significant increase of nociceptive threshold in the inflamed paw. Moreover, compounds 5c, 6a, 6b, 6c and 6d did not show any significant ulcerogenic activity.