Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents
Non-steroidal anti-inflammatory drugs (NSAIDs) are an important pharmacological class of drugs used for the treatment of inflammatory diseases. They are also characterized by severe side effects, such as gastrointestinal damage, increased cardiovascular risk and renal function abnormalities. In orde...
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doaj-d38f8512a3d74e7c82b9efbeccb258172020-11-25T00:42:39ZengMDPI AGMolecules1420-30492018-09-012310242510.3390/molecules23102425molecules23102425Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory AgentsAnamaria Cristina0Denisa Leonte1Laurian Vlase2László Csaba Bencze3Silvia Imre4Gabriel Marc5Bogdan Apan6Cristina Mogoșan7Valentin Zaharia8Department of Organic Chemistry, Iuliu Hațieganu University of Medicine and Pharmacy, Cluj-Napoca 400012, RomaniaDepartment of Organic Chemistry, Iuliu Hațieganu University of Medicine and Pharmacy, Cluj-Napoca 400012, RomaniaDepartment of Pharmaceutical Technology and Biopharmaceutics, Iuliu Hațieganu University of Medicine and Pharmacy, Cluj-Napoca 400012, RomaniaBiocatalysis and Biotransformation Research Group, Babeș-Bolyai University, Cluj-Napoca 400028, RomaniaDepartment of Analytical Chemistry and Drug Analysis, Tîrgu Mureș University of Medicine and Pharmacy, Târgu Mureș 540139, RomaniaDepartment of Pharmaceutical Chemistry, Iuliu Hațieganu University of Medicine and Pharmacy, Cluj-Napoca 400012, RomaniaDepartment of Pharmacology, Toxicology and Clinical Pharmacology, Iuliu Hațieganu University of Medicine and Pharmacy, Cluj-Napoca 400349, RomaniaDepartment of Pharmacology, Physiology and Pathophysiology, Iuliu Hațieganu University of Medicine and Pharmacy, Cluj-Napoca 400349, RomaniaDepartment of Organic Chemistry, Iuliu Hațieganu University of Medicine and Pharmacy, Cluj-Napoca 400012, RomaniaNon-steroidal anti-inflammatory drugs (NSAIDs) are an important pharmacological class of drugs used for the treatment of inflammatory diseases. They are also characterized by severe side effects, such as gastrointestinal damage, increased cardiovascular risk and renal function abnormalities. In order to synthesize new anti-inflammatory and analgesic compounds with a safer profile of side effects, a series of 2,6-diaryl-imidazo[2,1-b][1,3,4]thiadiazole derivatives 5a–l were synthesized and evaluated in vivo for their anti-inflammatory and analgesic activities in carrageenan-induced rat paw edema. Among all compounds, 5c showed better anti-inflammatory activity compared to diclofenac, the standard drug, and compounds 5g, 5i, 5j presented a comparable antinociceptive activity to diclofenac. None of the compounds showed ulcerogenic activity. Molecular docking studies were carried out to investigate the theoretical bond interactions between the compounds and target, the cyclooxygenases (COX-1/COX-2). The compound 5c exhibited a higher inhibition of COX-2 compared to diclofenac.http://www.mdpi.com/1420-3049/23/10/2425imidazo[2,1-b][1,3,4]thiadiazole derivativesanti-inflammatory activitymolecular dockingantinociceptive activity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Anamaria Cristina Denisa Leonte Laurian Vlase László Csaba Bencze Silvia Imre Gabriel Marc Bogdan Apan Cristina Mogoșan Valentin Zaharia |
spellingShingle |
Anamaria Cristina Denisa Leonte Laurian Vlase László Csaba Bencze Silvia Imre Gabriel Marc Bogdan Apan Cristina Mogoșan Valentin Zaharia Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents Molecules imidazo[2,1-b][1,3,4]thiadiazole derivatives anti-inflammatory activity molecular docking antinociceptive activity |
author_facet |
Anamaria Cristina Denisa Leonte Laurian Vlase László Csaba Bencze Silvia Imre Gabriel Marc Bogdan Apan Cristina Mogoșan Valentin Zaharia |
author_sort |
Anamaria Cristina |
title |
Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents |
title_short |
Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents |
title_full |
Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents |
title_fullStr |
Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents |
title_full_unstemmed |
Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents |
title_sort |
heterocycles 48. synthesis, characterization and biological evaluation of imidazo[2,1-b][1,3,4]thiadiazole derivatives as anti-inflammatory agents |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2018-09-01 |
description |
Non-steroidal anti-inflammatory drugs (NSAIDs) are an important pharmacological class of drugs used for the treatment of inflammatory diseases. They are also characterized by severe side effects, such as gastrointestinal damage, increased cardiovascular risk and renal function abnormalities. In order to synthesize new anti-inflammatory and analgesic compounds with a safer profile of side effects, a series of 2,6-diaryl-imidazo[2,1-b][1,3,4]thiadiazole derivatives 5a–l were synthesized and evaluated in vivo for their anti-inflammatory and analgesic activities in carrageenan-induced rat paw edema. Among all compounds, 5c showed better anti-inflammatory activity compared to diclofenac, the standard drug, and compounds 5g, 5i, 5j presented a comparable antinociceptive activity to diclofenac. None of the compounds showed ulcerogenic activity. Molecular docking studies were carried out to investigate the theoretical bond interactions between the compounds and target, the cyclooxygenases (COX-1/COX-2). The compound 5c exhibited a higher inhibition of COX-2 compared to diclofenac. |
topic |
imidazo[2,1-b][1,3,4]thiadiazole derivatives anti-inflammatory activity molecular docking antinociceptive activity |
url |
http://www.mdpi.com/1420-3049/23/10/2425 |
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