- 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
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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.
- 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.
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supporting information
(2021/03/17)
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- An efficient approach for the synthesis and antimicrobial evaluation of some new benzocoumarins and related compounds
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A convenient synthetic approach for pharmaceutically important benzocoumarin-based heterocyclic compounds has been studied. β-enaminonitrile has been used for the synthesis of a broad diversity of new benzocoumarins and related compounds over different reaction steps. Various synthetic approaches were used in this research for synthesis of heterocyclic systems such as acid-catalyzed hydrolysis, decarboxylation, deamination, ring opening and ring closure. The molecular structures of the newly synthesized derivatives were established by elemental analyses and spectral data (IR, 1H-NMR, and 13C-NMR). Some of the newly synthesized compounds were explored for their antimicrobial activities.
- Hekal, Mohamed H.,Abu El-Azm, Fatma S. M.,Samir, Sandy S.
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p. 2175 - 2186
(2021/05/27)
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- Design, Synthesis, and Characterization of Some Hybridized Pyrazolone Pharmacophore Analogs against Mycobacterium tuberculosis
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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.
- Krishnasamy, Sivakumar Kullampalayam,Namasivayam, Vigneshwaran,Mathew, Sincy,Eakambaram, Ragavendran S.,Ibrahim, Ibrahim A.,Natarajan, Adhirajan,Palaniappan, Senthilkumar
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p. 383 - 397
(2016/05/19)
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- Synthesis and antimicrobial activity of pyridopyrazole and pyrazolo[3,4-d]dihydrothiazole
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6-Methyl-1,3-dihydro-4H,7H-pyrazolo[2,3-c]pyridine-4-one (4) were synthesized by microwave as well as conventional method. The reaction time reduced 10 times than that of conventional method. The pyrazolo[3,4-d] dihydrothiazole (8) were synthesized by reacting phenylisothiocyanate with 1-carbethoxy-5-amino-pyrazol-4-ene-3-one and were screened for their antimicrobial activities.
- Deshmukh,Deshmukh,Jagtap,Suryavanshi,Jadhav,Anbhule
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experimental part
p. 613 - 616
(2010/07/08)
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- A novel synthesis of fused pyrazole systems as antimicrobial agents
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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.
- Erian, Ayman Wahba,El-Gohary,Manhi,Ali
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p. 748 - 751
(2007/10/03)
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- The Reactivity of β-Enaminonitriles Towards Amino-heterocycles: A Novel Synthesis of Fused Pyrazole Systems
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The pyrazolopyridine derivative 3 could be prepared by condensing β-aminocrotononitrile (1) with 3-aminopyrazolone derivative 2.A variety of new pyrazolopyrimidine systems are synthesized from the condensate product of 1 and cyanoacetohydrazide (6) with electrophilic reagents.A novel β-enaminonitrile 17 could be prepared via reaction of 1 and 4-aminoantipyrine (16) which reacted readily with benzaldehyde and benzylidenemalononitrile to give novel 1,4-dihydropyridines.
- Erian, Ayman Wahba,Aziz, Susan Ibrahim,Negm, Abdalla Mohamed,Sherif, Sherif Mourad
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p. 2301 - 2312
(2007/10/02)
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