Synthesis and characterization of some pyrazole derivatives of 1,5‐diphenyl‐1<i>H</i>‐pyrazole‐3,4‐dicarboxylic acid

Kasımoğulları, Rahmi; Arslan, Barış Seçkin

doi:10.1002/jhet.416

Cited by 12 publications

(3 citation statements)

References 34 publications

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“…The decarboxylation process took place at the carboxyl group that bonded the adjacent carbon to nitrogen of the pyrazole moiety. The regioselective decarboxylation of 7a is probably due to the hydrogen bonding between a lone pair of nitrogen and hydrogen atoms of the carboxylic group …”

Section: Resultsmentioning

confidence: 99%

Facile access to some new 3,3′‐bipyrazole‐ester derivatives utilizing bis‐hydrazonoyl chlorides

Dawood

Al-Fulaij

2019

Journal of Heterocyclic Chem

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The 1,3-dipolar cycloaddition reaction of bis-hydrazonoyl chlorides with ethyl propiolate and dimethyl acetylenedicarboxylate afforded diethyl 1,1 0 -aryl-3,3 0bipyrazole-4,4 0 -dicarboxylate and tetramethyl 1,1 0 -diaryl-3,3 0 -bipyrazole-4,4 0 ,5,5 0 -tetracarboxylate esters, respectively. Heating the latter two compounds with a mixture of HCl/AcOH furnished the same product: 3,3 0 -bipyrazole-5,5 0dicarboxylic acid. Reaction of the tetracarboxylate ester with aniline derivatives and with hydrazine gave the corresponding bipyrazole-fused heterocycles. Heating the dicarboxylic acid with 2-aminothiazole gave the corresponding bis-amide derivative. The structures of the products were established by elemental analysis, spectral data, and single-crystal X-ray crystallography. Synthesis of the 3,3 0bipyrazole derivatives 4, 7, 8, and 10 DAWOOD ET AL. 371 How to cite this article: Dawood KM, Elassar A-ZA, Al-Fulaij OA. Facile access to some new 3,3 0 -bipyrazole-ester derivatives utilizing bishydrazonoyl chlorides.

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Section: Resultsmentioning

confidence: 99%

Facile access to some new 3,3′‐bipyrazole‐ester derivatives utilizing bis‐hydrazonoyl chlorides

Dawood

Al-Fulaij

2019

Journal of Heterocyclic Chem

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“…Yield: 753 mg (95%) of brownish crystals. Physical and spectral data of carboxylic acid 24a were in agreement with the literature data …”

Section: Methodsmentioning

confidence: 95%

Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates

et al. 2015

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Seven title compounds 12a-g and the (S)-prolinate analogue 13 were prepared in five steps from 2-nitrobenzoic acid (7). Reduction of the nitro group followed by derivatization of the so formed anilines 14 gave the N-alkyl-(15a-c), N-acyl-(16a,b and 19), and N-vinyl derivative 20. NMR spectra of (S)-alanine and (S)-proline derived compounds 12, 13, 14-16, 19, and 20 exhibited two sets of signals corresponding to pairs of conformational diastereomers. The free energy barriers of rotation, ΔG(‡)298 = 82-86 kJ mol(-1), were determined by (1)H NMR for 12a, 12d, 12f, and 12g and evaluated by DFT calculations.

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“…The aforementioned starting compounds (1−5) are not novel and their characterization was previously made in the literature. [53][54][55] Finally, novel pyrazole-dicarboxamides (7a−j) were synthesized from the reaction of 5 with various primary and secondary sulfonamide derivatives (6a−j). [56] In this reaction, acid dichloride (5) was reacted with the sulfonamide derivative (6a-j) in the molar range of 1:4 in THF under reflux for 5 h to give the target products (7a−j) in high yields (see Scheme 1).…”

Section: Molecular Dockingmentioning

confidence: 99%

Synthesis, molecular docking analysis, drug‐likeness evaluation, and inhibition potency of new pyrazole‐3,4‐dicarboxamides incorporating sulfonamide moiety as carbonic anhydrase inhibitors

Özkul,

Tunca,

Mert

et al. 2024

J Biochem & Molecular Tox

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A series of novel pyrazole‐dicarboxamides were synthesized from pyrazole‐3,4‐dicarboxylic acid chloride and various primary and secondary sulfonamides. The structures of the new compounds were confirmed by FT‐IR, 1H‐NMR, 13C‐NMR, and HRMS. Then the inhibition effects of newly synthesized molecules on human erythrocyte hCA I and hCA II isoenzymes were investigated. Ki values of the compounds were in the range of 0.024−0.496 µM for hCA I and 0.006−5.441 µM for hCA II. Compounds 7a and 7i showed nanomolar level of inhibition of hCA II, and these compounds exhibited high selectivity for this isoenzyme. Molecular docking studies were performed between the most active compounds 7a, 7b, 7i, and the reference inhibitor AAZ and the hCAI and hCAII to investigate the binding mechanisms between the compounds and the isozymes. These compounds showed better interactions than the AAZ. ADMET and drug‐likeness analyses for the compounds have shown that the compounds can be used pharmacologically in living organisms.

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Synthesis and characterization of some pyrazole derivatives of 1,5‐diphenyl‐1H‐pyrazole‐3,4‐dicarboxylic acid

Cited by 12 publications

References 34 publications

Facile access to some new 3,3′‐bipyrazole‐ester derivatives utilizing bis‐hydrazonoyl chlorides

Facile access to some new 3,3′‐bipyrazole‐ester derivatives utilizing bis‐hydrazonoyl chlorides

Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates

Synthesis, molecular docking analysis, drug‐likeness evaluation, and inhibition potency of new pyrazole‐3,4‐dicarboxamides incorporating sulfonamide moiety as carbonic anhydrase inhibitors

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