New Synthetic Methods for Pyrazolesulfonyl Chlorides as Drug Precursors

Степанов, В. А.; Matyukhin, A. Yu.; Akkuzin, K. N.

doi:10.1007/s11094-017-1528-0

Cited by 2 publications

(3 citation statements)

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“…Except for 2d – 2h that were purchased, the substituted pyrazoles 2a – 2c were synthesized by the cyclization reaction starting from acyl acetones 1a – 1c , respectively . The substituted pyrazole-4-sulfonyl chlorides 3a – 3h were synthesized from the substituted pyrazoles 2a – 2h by the sulfonation reaction with chlorosulfonic acid and thionyl chloride . Then, using pyridine as the acid-binding agent and dichloromethane as the reaction solvent, the target compounds, namely pyrazole-4-sulfonohydrazide derivatives A1 – A12 and B1 – B12 , were expediently synthesized by the ammonolysis reaction of the intermediates 3 with substituted phenyl hydrazine under −5 °C to room temperature in yields of 47.3–90.3%.…”

Section: Results and Discussionmentioning

confidence: 99%

“…48 The substituted pyrazole-4-sulfonyl chlorides 3a−3h were synthesized from the substituted pyrazoles 2a−2h by the sulfonation reaction with chlorosulfonic acid and thionyl chloride. 49 Then, using pyridine as the acid-binding agent and dichloromethane as the reaction solvent, the target compounds, namely pyrazole-4-sulfonohydrazide derivatives A1−A12 and B1−B12, were expediently synthesized by the ammonolysis reaction of the intermediates 3 with substituted phenyl hydrazine under −5 °C to room temperature in yields of 47.3−90.3%. The structures of all of the synthesized target compounds were well characterized by 1 H NMR, 13 C NMR, and HRMS spectra.…”

Section: Resultsmentioning

confidence: 99%

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Potential Succinate Dehydrogenase Inhibitors Bearing a Novel Pyrazole-4-sulfonohydrazide Scaffold: Molecular Design, Antifungal Evaluation, and Action Mechanism

Chai

Mei

Tai

et al. 2023

J. Agric. Food Chem.

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Aiming to develop novel antifungal agents with a distinctive molecular scaffold targeting succinate dehydrogenase (SDH), 24 N′-phenyl-1H-pyrazole-4-sulfonohydrazide derivatives were first devised, synthesized, and verified by 1 H NMR, 13 C NMR, high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis. The bioassays revealed that the target compounds possessed highly efficient and broad-spectrum antifungal activities against four tested plant pathogenic fungi Rhizoctonia solani (R. solani), Botrytis cinerea, Fusarium graminearum, and Alternaria sonali. Strikingly, compound B6 was assessed as the selective inhibitor against R. solani, with an in vitro EC 50 value (0.23 μg/mL) that was similar to that of thifluzamide (0.20 μg/ mL). The in vivo preventative effect of compound B6 (75.76%) at 200 μg/mL against R. solani was roughly comparable to thifluzamide (84.31%) under the same conditions. The exploration of morphological observations indicated that compound B6 could strongly damage the mycelium morphology, obviously increase the permeability of the cell membrane, and dramatically increase the number of mitochondria. Compound B6 also significantly inhibited SDH enzyme activity with an IC 50 value of 0.28 μg/ mL, and its fluorescence quenching dynamic curves were similar to that of thifluzamide. Molecular docking and molecular dynamics simulations demonstrated that compound B6 could strongly interact with similar residues around the SDH active pocket as thifluzamide. The present study revealed that the novel N′-phenyl-1H-pyrazole pyrazole-4-sulfonohydrazide derivatives are worthy of being further investigated as the promising replacements of traditional carboxamide derivatives targeting SDH of fungi.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Potential Succinate Dehydrogenase Inhibitors Bearing a Novel Pyrazole-4-sulfonohydrazide Scaffold: Molecular Design, Antifungal Evaluation, and Action Mechanism

Chai

Mei

Tai

et al. 2023

J. Agric. Food Chem.

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“…The lower organic layer was separated, dried over sodium sulfate, and evaporated under vacuum to obtain 3,5-dimethyl-1 H -pyrazolesulfonyl chloride and 1,3,5-trimethyl-1 H -pyrazolesulfonyl chloride (Scheme ). − …”

Section: Experimental Conditionsmentioning

confidence: 99%

Antiproliferative Activity of New Pyrazole-4-sulfonamide Derivatives: Synthesis and Biological Evaluation

Mahesh,

Akshinthala,

Katari

et al. 2023

ACS Omega

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Pyrazole and sulfonamide constitute an important class of drugs, with several types of pharmacological agents. Facile synthesis of two new series of 3,5-dimethyl-1H-pyrazole-4-sulfonamide and 1,3,5-trimethyl-1H-pyrazole-4-sulfonamide derivatives was designed and synthesized. These pyrazole-4-sulfonamide derivatives are characterized by Fourier transform infrared (FT-IR), 1H NMR, 13C NMR, and elemental analysis, and their biological evolution data are presented. This paved way for the development of new pyrazole-4-sulfonamide derivatives. These compounds are tested for their in vitro antiproliferative activity against U937 cells by the CellTiter-Glo Luminescent cell viability assay using Mitomycin C. Cytotoxicity detection is based on the measurement of LDH activity, while these compounds did not exhibit cytotoxic activity on these cells. Half maximal inhibitory concentration (IC50) was calculated by Graph Pad Prism software for each dose. Their structure–activity relationships were obtained and discussed.

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New Synthetic Methods for Pyrazolesulfonyl Chlorides as Drug Precursors

Cited by 2 publications

References 1 publication

Potential Succinate Dehydrogenase Inhibitors Bearing a Novel Pyrazole-4-sulfonohydrazide Scaffold: Molecular Design, Antifungal Evaluation, and Action Mechanism

Potential Succinate Dehydrogenase Inhibitors Bearing a Novel Pyrazole-4-sulfonohydrazide Scaffold: Molecular Design, Antifungal Evaluation, and Action Mechanism

Antiproliferative Activity of New Pyrazole-4-sulfonamide Derivatives: Synthesis and Biological Evaluation

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