15264-63-8Relevant articles and documents
Design, synthesis and biological evaluation of triazole-oxadiazole conjugates for the management of cognitive dysfunction
Jain, Ankit,Piplani, Poonam
, (2020)
Acetylcholinesterase has been a promising target for the development of putative therapeutics against cognitive decline. The deleterious effect of oxidative stress on the learning and memory paradigms of an individual has also been well documented. In view of this, the present study demonstrates the design, synthesis and pharmacological evaluation of triazole-oxadiazole conjugates. Eighteen novel hybrids (6–23) have been synthesised by employing suitable synthetic procedures and characterized by various spectral and elemental techniques. Further these synthesised compounds were evaluated against behavioural alterations using step down passive avoidance and escape learning protocol at a dose of 0.5 mg/kg with reference to the standard, donepezil. All the synthesised compounds were evaluated for their in vitro acetylcholinesterase (AChE) inhibition at five different concentrations using mice brain homogenate as the source of the enzyme. Biochemical estimation of markers of oxidative stress (lipid peroxidation, superoxide dismutase, glutathione and catalase) has also been carried out to assess the role of synthesised molecules on the oxidative damage induced by scopolamine. The compounds 13, 17 and 23 displayed appreciable activity towards acetylcholinesterase inhibition. These compounds also decreased scopolamine induced oxidative stress, thus serving as promising leads for the amelioration of oxidative stress induced cognitive decline. The molecular docking study performed to predict the binding mode of the compounds also suggested that these compounds bind appreciably to the amino acids present in the active site of the recombinant human acetylcholinesterase (rhAChE). The results indicated that these compounds could be further traversed as inhibitors of AChE and oxidative stress for the treatment of cognitive dysfunction.
Crystal Structure of 2-(Pyridin-4-yl)-5-(Undecylthio)-1,3,4-Oxadiazole
Shen,Wang,Sun,Wu,Tan,Weng,Liu
, p. 1236 - 1240 (2018)
The title compound 2-(pyridin-4-yl)-5-(undecylthio)-1,3,4-oxadiazole (C18H27ON3S) is synthesized, and its structure is confirmed by 1H NMR, MS, elemental analyses and X-ray diffraction. It crystallizes in the monoclinic system, space group P2(1)/c with a = 24.453(17) ?, b = 10.604(7) ?, c = 7.095(5) ?, β = 91.60(2)°, V = 1839(2) ?3, Z = 4, and R = 0.086 for 2295 observed reflections with I > 2σ(I). The preliminary biological test shows that the title compound has good activity against Pythium ultimum with inhibitory to be 77.78%.
ZnCl2 catalyzed efficient synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole
Rahman, Md.A.,Karim, Mohammad R.,Arifuzzaman, Md.,Siddiquee, Tasneem A.,Mirza, Aminul H.
, p. 3267 - 3273 (2014)
New methods for the synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole have been described. No cyclizations took place in the absence of ZnCl 2. 1,3,4-Thiadiazoles are formed in the presence of ZnCl2 alone, whereas oxadiazoles are produced when a base such as Et3N or KOH was used along with ZnCl2. % Yields are optimized.
Facile conversion of acyldiithiocarbazinate salts to 1,3,4-oxadiazole derivatives under microwave irradiation
Joshi, Sachin,Karnik
, p. 111 - 114 (2002)
Microwave irradiation is found to be especially suitable for salts, as illustrated by the conversion of acyldithocarbazinate salts 1 to 5-substituted-2-mercapto 1,3,4-oxadiazoles 2. This method reduced the reaction time to a few seconds.
Synthesis and tuberculostatic activity of methyl 3-isonicotinoyl-dithiocarbazate and S,S′-dimethyl dithiocarbonate isonicotinoylhydrazone, and their reactions with amines and hydrazines
Foks,Mieczkowska,Janowiec,Zwolska,Andrzejcyk
, p. 810 - 816 (2002)
Methyl 3-isonicotinoyldithiocarbazates and S,S′-dimethyl dithiocarbonate isonicotinoylhydrazone were prepared. Their reactions with primary and secondary amines, diamines, and hydrazines were studied. The newly obtained derivatives did not show tuberculostatic activity in vitro.
Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents
Yarmohammadi, Elahe,Beyzaei, Hamid,Aryan, Reza,Moradi, Ashraf
, p. 2367 - 2378 (2020/08/10)
Abstract: One of the goals of green chemistry is to use environmentally friendly solvents or remove and reduce the volume of harmful spent solvents. In this study, a novel process for the synthesis of 5-substituted 1,3,4-oxadiazole-2-thiol derivatives was proposed via ultrasound-assisted reaction of aryl hydrazides with CS2 (1:1 molar ratio) in some drops of DMF in the absence of basic or acidic catalysts. They were produced in good to excellent yields under easy workup and purification conditions. In order to prove the usefulness of the prepared compounds, their antioxidant, antibacterial, and antifungal potentials were screened by DPPH free radical scavenging, serial twofold microdilution and streak plate methods. Acceptable to significant inhibitory activities were observed with synthesized heterocycles. The results showed that 5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thiol (3c) is an broad-spectrum antimicrobial agent. Many of them displayed remarkable antioxidant properties comparable to standard controls (ascorbic acid and α-tocopherol). Synthesized 1,3,4-oxadiazoles are also potent candidates to treat cancer, Parkinson, inflammatory, and diabetes diseases. Graphic Abstract: Eighteen 5-substituted 1,3,4-oxadiazole-2-thiol derivatives as potent antimicrobial and antioxidant agents were prepared via a new, efficient and green procedure.[Figure not available: see fulltext.].
Synthesis of 5-(Pyridin-4-yl)-oxadiazole Derivatives from Isoniazid and Evaluation of their Antimicrobial and Antitubercular Activities
Asif, Mohammad,Kamal, Mehnaz
, p. 45 - 50 (2021/04/22)
Some new 5-(pyridin-4-yl)-1,3,4-oxadiazole derivatives were synthesized from isoniazid and evaluated for their antimicrobial and antitubercular activity. Isoniazid was treated with CS2 to obtain 5-(pyridin-4-yl)-1,3,4-oxadiazole-2-thiol (1), which was then hydrazinolyzed to obtain 2-hydrazinyl-5-(pyridin-4-yl)-1,3,4-oxadiazole (2). Cyclization of compound 2 afforded 6-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]oxadiazole (3) and 6-(pyridin-4-yl)-[1,3,4]oxadiazolo[3,2-d]tetrazole (4). Shciff’s bases (5 and 6) were synthesized by the reaction of compound 2 with furfuraldehyde and thiophene-2-aldehyde, respectively. Synthesized compounds were characterized using infrared (IR), 1H-nuclear magnetic resonance (NMR), 13C-NMR, and mass spectrometry. Antibacterial activity of all the compounds (1-6) was tested against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli bacterial species, and antifungal activity was tested against Candida albicans and Aspergillus niger fungal species and compared with reference drug amoxicillin for antibacterial activity and miconazole for antifungal activity. The antitubercular activity of the compounds 1-6 was tested against Mycobacterium tuberculosis H37Rv strain. Among all the compounds, compounds 2 and 6 displayed promising antibacterial, antifungal, and antitubercular activities and would be an effective candidate.
