Microwave-assisted synthesis of pyrano[2,3-c]-pyrazole derivatives and their anti-microbial, anti-malarial, anti-tubercular, and anti-cancer activities

Parikh, Paranjay; Timaniya, Jignesh B.; Patel, Mrugesh; Patel, Kaushal P.

doi:10.1016/j.molstruc.2021.131605

Cited by 36 publications

(16 citation statements)

References 55 publications

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“…A series of 6-amino-1,4-dihydropyrano[2,3- c ]pyrazole-5-carbonitriles 127 were synthesized in high yields via a one-pot multicomponent approach [ 114 ]. Initially, a mixture of β -keto esters 8 , aryl hydrazines 15 , and zinc triflate (10 mol%) was irradiated under microwave at 80 °C for 10 min.…”

Section: Multicomponent Synthesis Of Biologically Active Pyrazole Der...mentioning

confidence: 99%

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

2022

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Pyrazole and its derivatives are considered a privileged N-heterocycle with immense therapeutic potential. Over the last few decades, the pot, atom, and step economy (PASE) synthesis of pyrazole derivatives by multicomponent reactions (MCRs) has gained increasing popularity in pharmaceutical and medicinal chemistry. The present review summarizes the recent developments of multicomponent reactions for the synthesis of biologically active molecules containing the pyrazole moiety. Particularly, it covers the articles published from 2015 to date related to antibacterial, anticancer, antifungal, antioxidant, α-glucosidase and α-amylase inhibitory, anti-inflammatory, antimycobacterial, antimalarial, and miscellaneous activities of pyrazole derivatives obtained exclusively via an MCR. The reported analytical and activity data, plausible synthetic mechanisms, and molecular docking simulations are organized in concise tables, schemes, and figures to facilitate comparison and underscore the key points of this review. We hope that this review will be helpful in the quest for developing more biologically active molecules and marketed drugs containing the pyrazole moiety.

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Section: Multicomponent Synthesis Of Biologically Active Pyrazole Der...mentioning

confidence: 99%

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

2022

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“…Heterocyclic compounds bearing pyranopyrazole motifs have many biological and pharmaceutical applications. In particular, dihydropyrano [2, 3-c] pyrazole is a valuable compound due to antiinflammatory [13], antimicrobial [14], anti-tubercular, and anti-tumors [15] (Fig. 1.).…”

Section: Scheme 1 Structure Of κ-Carrageenanmentioning

confidence: 99%

Preparation of magnetized carrageenan-metformin as a new bio-inspired heterogeneous nanocatalyst for the synthesis of dihydropyrano[2,3- c]pyrazoles

Heydari

Bakhtiarian

Khodaei

2023

Preprint

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Due to environmental concerns, there is a growing interest in the eco-friendly and reusable nanocatalysts. However, preparing a benign and reusable nanomaterial with high catalytic activity is an issue of challenge. A good strategy is the modification of polysaccharides with catalytically active species followed by magnetization. Therefore, we introduced a kappa-carrageenan (Carr) based nanocatalyst modified by metformin (Met) coated on Fe3O4 nanoparticles (MNPs). After thorough physicochemical characterization, the as-synthesized Carr-Met-MNPs nanocomposites demonstrated a high activity as a multifunctional nanomaterial for the four-component domino synthesis of dihydropyrano [2, 3-c] pyrazole derivatives via condensation of hydrazine hydrate, ethyl acetoacetate, malononitrile, and aromatic aldehydes. The synergistic effect of sulfonic acid and amino groups can justify the high performance of Carr-Met-MNPs nanocomposites. These nanocomposites with properties including benign solvent system, improved activity, and easy recoverability (up to 5 runs) can be quite comparable to other heterogeneous and homogeneous catalyst systems. The heterogeneity of Carr-Met-MNPs nanocomposites was also appraised by a hot filtration test under optimum reaction conditions.

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“…Heterocyclic compounds bearing pyranopyrazole motifs have many biological and pharmaceutical applications. In particular, dihydropyrano [2, 3-c] pyrazole is a valuable compound due to anti-in ammatory [13], antimicrobial [14], anti-tubercular, and anti-tumors [15] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Magnetized metformin-functionalized carrageenan as a solid acid-base bifunctional nanocatalyst for the one-pot synthesis of dihydropyrano[2,3- c]pyrazoles

Heydari

Bakhtiarian

Khodaei

2023

Preprint

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In the current work we introduced a magnetic nanocatalyst with acidic-basic properties by coating Fe3O4 magnetic nanoparticles with kappa-carrageenan (Carr) and metformin (Met) moieties. The successful synthesis of Carr-Met-MNPs nanoparticles was verified by FT-IR, XRD, VSM, FESEM, EDX-mapping and TGA. The acidic-basic properties of Carr-Met-MNPs were studied by titration. The Carr-Met-MNPs nanoparticles demonstrated very good to excellent yields (88-94%) for the four-component domino synthesis of dihydropyrano [2, 3-c] pyrazoles via condensation of hydrazine hydrate, ethyl acetoacetate, malononitrile, and aromatic aldehydes in the aqueous ethanol as a benign solvent system. The synergistic effect of sulfonic acid and amino groups can justify the catalytic activity of Carr-Met-MNPs. Also, the catalyst can be magnetically recovered. Simplicity of catalyst synthesis, use of a benign solvent system, improved activity, and easy recoverability (up to 5 runs) is some of prominent advantages of the present catalyst system. The heterogeneity of Carr-Met-MNPs nanocomposites was also confirmed by a hot filtration test under optimum reaction conditions.

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Microwave-assisted synthesis of pyrano[2,3-c]-pyrazole derivatives and their anti-microbial, anti-malarial, anti-tubercular, and anti-cancer activities

Cited by 36 publications

References 55 publications

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

Preparation of magnetized carrageenan-metformin as a new bio-inspired heterogeneous nanocatalyst for the synthesis of dihydropyrano[2,3- c]pyrazoles

Magnetized metformin-functionalized carrageenan as a solid acid-base bifunctional nanocatalyst for the one-pot synthesis of dihydropyrano[2,3- c]pyrazoles

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