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.