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
5University 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
*corresponding author: vzaharia@umfcluj.ro
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Abstract:
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.

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