127222-70-2Relevant academic research and scientific papers
Synthesis, anti-inflammatory activity, and molecular docking studies of some novel Mannich bases of the 1,3,4-oxadiazole-2(3H)-thione scaffold
Ozyazici, Tugce,Gurdal, Enise E.,Orak, Duygu,Sipahi, Hande,Ercetin, Tuba,Gulcan, Hayrettin O.,Koksal, Meric
, (2020/04/28)
A series of novel ibuprofen and salicylic acid-based 3,5-disubstituted-1,3,4-oxadiazole-2(3H)-thione derivatives was synthesized, and they were evaluated as potential anti-inflammatory agents. Following the structure identification studies employing IR, 1H nuclear magnetic resonance (NMR), 13C NMR, and elemental analysis, the title compounds were tested by cyclooxygenase (COX)-1 and COX-2 inhibition assays concomitant to lipopolysaccharide (LPS)-induced nitric oxide and prostaglandin production prevention experiments. The results indicated that the majority of the compounds displayed either a superior or comparable activity in preventing both LPS-induced NO production and COX-1 activity in comparison to the activities of the reference molecules. Furthermore, docking studies were also performed to reveal possible interactions with the COX enzymes.
Novel 1,3,4-oxadiazole/oxime hybrids: Synthesis, docking studies and investigation of anti-inflammatory, ulcerogenic liability and analgesic activities
Abd-Ellah, Heba S.,Abdel-Aziz, Mohamed,Shoman, Mai E.,Beshr, Eman A.M.,Kaoud, Tamer S.,Ahmed, Al-Shaimaa F.F.
supporting information, p. 48 - 63 (2016/09/28)
A novel group of 1,3,4-oxadaiazoles, a group known for their anti-inflammatory activity, is hybridized with nitric oxide (NO) releasing group, oxime, for its gastro-protective action and potential synergistic effect. The synthesized hybrids were evaluated for their anti-inflammatory, analgesic, antioxidant and ulcerogenic activities. Most of the tested compounds showed excellent anti-inflammatory activity with compound 8e being more active than indomethacin. They also showed moderate analgesic activity but no antioxidant one. The ability of the synthesized compounds to inhibit COX-1 and COX-2 is studied and the prepared compounds were able to inhibit both COXs non-selectively with IC50s of 0.75–70.50?μM. Docking studies revealed the mode of interaction of the tested compounds into the empty pocket of the isozymes. All of the synthesized compounds interact with COXs active site with energy scores comparable to that of ibuprofen. All compounds showed a safer profile on the stomach tissue integrity compared to conventional NSAIDs. The designed strategy was applied to ibuprofen to introduce ibuprofen/oxadiazole/NO hybrid. The synthesized ibuprofen hybrid is a promising alternative to ibuprofen having similar anti-inflammatory activity but with safer GIT profile.
Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives
Manjunatha,Poojary, Boja,Lobo, Prajwal L.,Fernandes, Jennifer,Kumari, N. Suchetha
experimental part, p. 5225 - 5233 (2011/01/04)
The acid hydrazides (2) derived from ibuprofen and 4-methylthiophenyl acetic acids have been subjected to cyclization with carbon disulphide under basic conditions to yield 1,3,4-oxadiazol-2-thiones (3) which on aminomethylation with formaldehyde and secondary amines afforded a series of Mannich bases (4 and 5). Purity of the compounds has been confirmed by TLC. Structures of these compounds were established on the basis of elemental analyses and spectral studies. The newly synthesized compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic and antimicrobial activities.
