6126-22-3Relevant articles and documents
Synthesis of α-substituted 2-(1H-1,2,4-triazol-3-yl)acetates and 5-amino-2,4-dihydro-3H-pyrazol-3-ones via the Pinner strategy
Khomenko, Dmytro M.,Doroshchuk, Roman O.,Ivanova, Hanna V.,Zakharchenko, Borys V.,Raspertova, Ilona V.,Vaschenko, Oleksandr V.,Shova, Sergiu,Dobrydnev, Alexey V.,Moroz, Yurii S.,Grygorenko, Oleksandr O.,Lampeka, Rostyslav D.
supporting information, (2021/03/17)
A series of 2-(1H-1,2,4-triazol-3-yl)acetates, as well as 4-mono- and 4,4-disubstituted 5-amino-2,4-dihydro-3H-pyrazol-3-ones (including spirocyclic derivatives) have been synthesized using the Pinner reaction strategy. α-Mono- and α,α-disubstituted ethyl cyanoacetates were converted into the corresponding carboxyimidate salts that served as the key intermediates. Their further reaction with formylhydrazide or hydrazine hydrate provided triazolylacetates or aminopyrazolones (including spirocyclic derivatives), depending on the structure of the starting Pinner salt and the nature of the nucleophile. The scope and limitations of the developed synthetic method have been established.
Design, Synthesis, and Characterization of Some Hybridized Pyrazolone Pharmacophore Analogs against Mycobacterium tuberculosis
Krishnasamy, Sivakumar Kullampalayam,Namasivayam, Vigneshwaran,Mathew, Sincy,Eakambaram, Ragavendran S.,Ibrahim, Ibrahim A.,Natarajan, Adhirajan,Palaniappan, Senthilkumar
, p. 383 - 397 (2016/05/19)
Twenty-seven hybridized pyrazolone analogs were designed, docked, synthesized in two series and evaluated for their in vitro antimycobacterial properties. In the first series, four Schiff base derivatives, 6b, 7b, 7h, and 7i, show good antitubercular activity with minimum inhibition concentration (MIC) values in the range of 32.56-42.55 μM. In the second series, two compounds, 8b and 8c, possessed significant antitubercular activity with MIC 630. Compounds 8b and 8c showed shikimate kinase inhibition activity at 5.84 and 6.93 μM, respectively. The activity and docking results lead to the conclusion that the compounds without double bond in the imine side chain and hydrophobic clashes at the pyrazolone end are necessary for good accommodation in the binding pocket and for imparting flexibility. All the compounds were also tested for antimicrobial activity (antibacterial and antifungal) and show highly significant activities against all the microorganisms tested. Hybridized pyrazolone analogs were designed, docked, and synthesized in two series. Both compound series were evaluated for their in vitro antimycobacterial properties, showing highly significant activities against all microorganisms tested. No double bond in the imine side chain and hydrophobic clashes at the pyrazolone end were necessary for good accommodation in the binding pocket of shikimate kinase.
A novel synthesis of fused pyrazole systems as antimicrobial agents
Erian, Ayman Wahba,El-Gohary,Manhi,Ali
, p. 748 - 751 (2007/10/03)
The pyrazolo[3,4-b]pyridine derivatives 3 could be prepared by condensing compounds 1 with the 3-aminopyrazolone derivative 2. The pyrazolo[5,2-b]-1,3-oxazine derivative 11 and polyfunctionally substituted 1,4-dihydropyridines 15, 18 were also synthesized. Some of the obtained compounds were tested for their antimicrobial activity.
