Novel 1,4-dihydropyrano[2,3-c]pyrazole derivatives: Synthesis, characterization, biological evaluation and in silico study

Vasava, Mahesh S.; Bhoi, Manoj N.; Rathwa, Sanjay K.; Shetty, Shilpa; Patel, Rikin D.; Rajani, Dhanji P.; Rajani, Smita D.; Patel, Anant B.; Pandya, Himanshu; Patel, Hitesh D.

doi:10.1016/j.molstruc.2018.12.053

Cited by 25 publications

(24 citation statements)

References 51 publications

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“…Analytical Techniques. The 1 H and 13 C NMR spectra were recorded on a Bruker Advance 500 instrument using DMSO-d 6 as solvent and the solvent peaks as a reference. HRMS (ESI) data were collected using a Bruker micrOTOF-QII MS instrument at 80 eV.…”

Section: Introductionmentioning

confidence: 99%

A New Pathway for the Preparation of Pyrano[2,3-c]pyrazoles and molecular Docking as Inhibitors of p38 MAP Kinase

Nguyen

Truong

et al. 2022

ACS Omega

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We report a new pathway to synthesize pyrano[2,3- c ]pyrazoles and their binding mode to p38 MAP kinase. Pyrano[2,3- c ]pyrazole derivatives have been prepared through a four-component reaction of benzyl alcohols, ethyl acetoacetate, phenylhydrazine, and malononitrile in the presence of sulfonated amorphous carbon and eosin Y as catalysts. All products were characterized by melting point, 1 H and 13 C NMR, and HRMS (ESI). The products were screened in silico for their binding activities to both the ATP-binding pocket and the lipid-binding pocket of p38 MAP kinase, using a structure-based flexible docking provided by the engine ADFR. The results showed that eight synthesized compounds had a higher affinity to the lipid pocket than to the other target site, which implied potential applications as allosteric inhibitors. Finally, the most biologically active compound, 5 , had a binding affinity comparable to those of other proven lipid pocket inhibitors, with affinity to the target pocket reaching −10.9932 kcal/mol, and also had the best binding affinity to the ATP-binding pockets in all of our products. Thus, our research provides a novel pathway for synthesizing pyrano[2,3- c ]pyrazoles and bioinformatic evidence for their biological capability to block p38 MAP kinase pockets, which could be useful for developing cancer or immune drugs.

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Section: Introductionmentioning

confidence: 99%

A New Pathway for the Preparation of Pyrano[2,3-c]pyrazoles and molecular Docking as Inhibitors of p38 MAP Kinase

Nguyen

Truong

et al. 2022

ACS Omega

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“…Once the compound showed better value in the bioassay tests, it will begin process of drug development prior to clinical trials. [7] Constituting an important heterocyclic scaffold with a rich bioactive profile in medicinal chemistry, dihydropyrano[2,3-c]pyrazole skeleton exhibits anticancer, [8] antimicrobial, [9] antioxidant [10] and anti-inflammatory properties. [11] Besides, they also showed DNA-binding ability [12] and potential inhibitors of cholinesterases.…”

Section: Introductionmentioning

confidence: 99%

An Agro‐Waste Based Eco‐Friendly Synthesis, Electrochemical Behavior and Anti‐oxidant Properties Evaluation of Pyrano[2,3‐c]pyrazole and Pyrazolyl‐4H‐chromenes Derivatives

et al. 2022

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An efficient and economical one-pot synthesis of pyrano [2,3-c] pyrazoles and pyrazolyl-4H-chromenes using Water Extract of Mango Peel Ash (WEMPA) as a natural aqueous medium catalysts under microwave irradiation described. The microwave irradiation enhances the rate of the reaction, and decreases by-product formation. The catalyst is obtained from the agro-waste feedstock, by simple thermal treatment of dry peel of mango fruit followed by extraction of the resulted ash in water gave catalytic green solvent medium. In continuation of our research work on developing green chemistry protocol for bioactive molecule synthesis, herein, first time described pyrano[2,3-c]pyrazole and pyrazolyl-4H-chromene derivative synthesis by the reaction of hydrazine hydrate (1), malononitrile (2), ethyl acetoacetate (3), aryl aldehydes (4), and/or salicylaldehyde (5). Some of the selected pyrano[2,3-c]pyrazole ( 6) and pyrazolyl-4H-chromene (7) derivatives are tested for their in vitro antioxidant activity (free radical scavenging) by DPPH assay method. The assay result revealed, compounds 6 a, 6 h, 6 i and 7 d showed significant antioxidant activities comparison with refrence ascorbic acid. Some of the selected derivatives are characterized by FT-IR, 1 H-, 13 C-NMR and mass spectrometry analysis, and also tested for their electrochemical behavior studies using a cyclic voltammetry.[a] K.

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“…Pyran derivatives are a class of oxygen containing heterocyclic scaffold with a wide variety of pharmacological and biological prope rties, such as anti-cancer, [15] anti-tumor, [16] antiviral [17] and anti-microbial. [18] Similarly, pyrazolopyran derivatives are important class of heterocyclic moieties having an essential function in medicinal chemistry due to in various biological activities like anti-microbial, [19] anti-inflammatory, [20] anti-bacterial [21] etc. Therefore, good efforts have been made by chemists for the synthesis of these heterocyclic scaffolds using numerous methodologies.…”

Section: Introductionmentioning

confidence: 99%

Fe₃O₄@RB@LDH: Efficient and Recyclable Photocatalyst Visible‐Light Mediated Synthesis of Pyran and Pyrrolidinone Derivatives and Their Anti‐Microbial Activities

et al. 2022

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Selective and high yielding synthesis of pyran and pyrrolidinone derivatives through a magnetic layered double hydroxide (LDH) visible light photocatalyst (VLPC)-promoted reaction is reported. The catalyst was prepared and characterized by various analytical techniques. Since it is magnetic the prepared catalyst could be easily separated from the reaction mixture by using an external magnet. The advantages of this synthetic protocol are good to excellent yields, short reaction times, easy catalyst recovery and recyclability. Also, in vitro antibacterial screening of pyrrolidinone derivative was studied against gram-positive Bacillus cereus (B. cereus), gram-negative bacteria Escherichia coli (E. coli) and S. aureus. Compound 9 f [Methyl-2-(3-chlorophenyl)-2,5-dihydro-4-hydroxy-5-oxo-1-phenyl-1Hpyrrole-3-carboxylate] exhibited the maximum activity against all the bacteria tested in the experiment.

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Novel 1,4-dihydropyrano[2,3-c]pyrazole derivatives: Synthesis, characterization, biological evaluation and in silico study

Cited by 25 publications

References 51 publications

A New Pathway for the Preparation of Pyrano[2,3-c]pyrazoles and molecular Docking as Inhibitors of p38 MAP Kinase

A New Pathway for the Preparation of Pyrano[2,3-c]pyrazoles and molecular Docking as Inhibitors of p38 MAP Kinase

An Agro‐Waste Based Eco‐Friendly Synthesis, Electrochemical Behavior and Anti‐oxidant Properties Evaluation of Pyrano[2,3‐c]pyrazole and Pyrazolyl‐4H‐chromenes Derivatives

Fe₃O₄@RB@LDH: Efficient and Recyclable Photocatalyst Visible‐Light Mediated Synthesis of Pyran and Pyrrolidinone Derivatives and Their Anti‐Microbial Activities

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Novel 1,4-dihydropyrano[2,3-c]pyrazole derivatives: Synthesis, characterization, biological evaluation and in silico study

Cited by 25 publications

References 51 publications

A New Pathway for the Preparation of Pyrano[2,3-c]pyrazoles and molecular Docking as Inhibitors of p38 MAP Kinase

A New Pathway for the Preparation of Pyrano[2,3-c]pyrazoles and molecular Docking as Inhibitors of p38 MAP Kinase

An Agro‐Waste Based Eco‐Friendly Synthesis, Electrochemical Behavior and Anti‐oxidant Properties Evaluation of Pyrano[2,3‐c]pyrazole and Pyrazolyl‐4H‐chromenes Derivatives

Fe3O4@RB@LDH: Efficient and Recyclable Photocatalyst Visible‐Light Mediated Synthesis of Pyran and Pyrrolidinone Derivatives and Their Anti‐Microbial Activities

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Fe₃O₄@RB@LDH: Efficient and Recyclable Photocatalyst Visible‐Light Mediated Synthesis of Pyran and Pyrrolidinone Derivatives and Their Anti‐Microbial Activities