1,3‐Dipolar Cycloaddition of Nitrile Imines with Cyclic α‐β‐Unsaturated Ketones: A Regiochemical Route to Ring‐Fused Pyrazoles

Chandanshive, Jay Zumbar; Bonini, Bianca F.; Tiznado, William; Escobar, Carlos A.; Caballero, Julio; Femoni, Cristina; Fochi, Mariafrancesca; Franchini, Mauro Comes

doi:10.1002/ejoc.201100558

Cited by 25 publications

(9 citation statements)

References 52 publications

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“…The Chemistry of fused pyrazolo- and thieno-pyrazole moieties has drawn great attention due to their pharmacological importance as reported earlier [29, 30, 31]. M. G. Prabhudeva et al, in 2018 reported the synthesis of bioactive thiophene-pyrazole conjugates and screened further for their antimicrobial and anti-oxidant properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity

Puthran

Poojary

Purushotham

et al. 2019

Heliyon

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2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile have been synthesized from 1-(3-fluoro-4-methoxyphenyl)ethanone, malononitrile, a mild base and sulfur powder using Gewald synthesis technique and the intermediate was treated with 1,3-disubstituted pyrazole-4-carboxaldehyde to obtain the novel Schiff bases. 1,3-disubstituted pyrazole-4-carboxaldehyde derivatives have been synthesized by Vilsmeier-Haack reaction in the course of a multi-step reaction. The structure of novel compounds were established on the basis of their elemental analyses IR, 1 H NMR, 13 C NMR, and mass spectral data and then screened for their in vitro antimicrobial activity. Among them 5a, 5c, 5f and 5h showed excellent activity when compared to other derivatives. Remaining derivatives showed moderate activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity

Puthran

Poojary

Purushotham

et al. 2019

Heliyon

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“…10 Moreover, the chemistry of fused pyrazole derivatives has received great attention due to their pharmacological importance. 11,12 It has been found that pyranopyrazoles are an important class of biologically active heterocycles. They are reported to possess a multiplicity of pharmacological properties including anticancer, 13 antimicrobial, 14 anti-inflammatory, 15 insecticidal and molluscicidal activities.…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis, Characterization, Cytotoxicity and Toxicity of Pyrazole Derivatives

Kamel

2015

ACSi

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The reaction of 1 with phenylisothiocyanate followed by treatment with the α-halocarbonyl compounds 24a-c afforded the thiazole derivatives 25a-c. The synthesized products were evaluated for their cytotoxicity against cancer and normal cell lines. Most compounds showed significant anticancer activity without affecting the normal fibroblast cells. The toxicity of the most pontent cytotoxic compounds was measured using Brine-Shrimp Lethality Assay.

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“…Many literature reviews suggest that the pharmacophore hybrids may have enhanced efficacy, fewer drug–drug interactions, and less potential to induce drug resistance [ 26 ]. In light of the significance of pyrazoles and thiazoles, numerous studies have been conducted on the synthesis and biological evaluations of new hybrid pharmacophores containing pyrazole and thiazole moieties [ 27 , 28 , 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Biological Evaluation of Some Novel Pyrazolo[5,1-b]thiazole Derivatives as Potential Antimicrobial and Anticancer Agents

et al. 2021

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The pharmacological activities of thiazole and pyrazole moieties as antimicrobial and anticancer agents have been thoroughly described in many literature reviews. In this study, a convenient synthesis of novel pyrazolo[5,1-b]thiazole-based heterocycles was carried out. The synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy and mass spectrometry. Some selected examples were screened and evaluated for their antimicrobial and anticancer activities and showed promising results. These products could serve as leading compounds in the future design of new drug molecules.

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1,3‐Dipolar Cycloaddition of Nitrile Imines with Cyclic α‐β‐Unsaturated Ketones: A Regiochemical Route to Ring‐Fused Pyrazoles

Cited by 25 publications

References 52 publications

Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity

Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity

Convenient Synthesis, Characterization, Cytotoxicity and Toxicity of Pyrazole Derivatives

Synthesis, Characterization, and Biological Evaluation of Some Novel Pyrazolo[5,1-b]thiazole Derivatives as Potential Antimicrobial and Anticancer Agents

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