Pd-catalyzed post-Ugi intramolecular cyclization to the synthesis of isoquinolone-pyrazole hybrid pharmacophores &amp; discover their antimicrobial and DFT studies

Pandya, Keyur M.; Battula, Satyanarayana; Naik, Parth

doi:10.1016/j.tetlet.2021.153353

Cited by 11 publications

(12 citation statements)

References 44 publications

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“…The Ugi multicomponent reaction (MCR) is one of the most predominant isocyanide-based MCRs, attracting a wide diversity of fascinated chemists owing to its four-component transformation and remarkable functional tolerance [ 37 , 38 ]. Viewing the significance of the N -containing heterocycles (particularly pyrazole and isoquinolone derivatives) in countless areas, mainly in medicinal chemistry, a Ugi-mediated research work focused on the synthesis of the hybrid molecules of these two structural pharmacophores was undertaken [ 39 ]. Thus, the microwave-assisted ligand-free palladium-catalyzed post-Ugi reaction for the synthesis of isoquinolone and pyrazole-mixed pharmacophore derivatives 41 was achieved from pyrazole-substituted amides 40 (synthesized using the Ugi reaction).…”

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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“…tried the isocyanide insertion into the structure 75 , and encountered a tandem O‐cyclization/ring opening/N‐cyclization via the removal of a 2‐methylpropene, yielding isoquinolin‐1(2 H )‐ones 76 (Scheme 26). [44] A similar pathway was employed for the synthesis of pyrazole‐substituted isoquinolines [45] …”

Section: Synthesis Of Six‐membered Heterocyclesmentioning

confidence: 99%

“…[44] A similar pathway was employed for the synthesis of pyrazole-substituted isoquinolines. [45] Moni et al developed an intriguing approach to the synthesis of 3-hydroxyisoquinolines 79 and furo[2,3c]isoquinolines 80 (Scheme 27). The Ugi adducts 77 were tolerated in the reductive Heck coupling reaction, passing from the corresponding intermediate 78 to give 3-hydroxyisoquinolines 79.…”

Section: Chemistryselectmentioning

confidence: 99%

Annulation of the Ugi Products Using Palladium Catalysts

2022

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For almost half a century of efforts to make them, the importance of Ugi products has substantially expanded because they are used as precursors for the synthesis of more complex structures, such as peptides, amino acids, pharmaceutical compounds, and heterocycles. Through the introduction of a double or triple bond along with a carbon‐halide bond in the starting materials, the Ugi adduct can be cyclized through Pd‐catalyzed intramolecular reactions to create sophisticated heterocycles. This article discusses the role of palladium in the catalytic cyclization of the Ugi adducts and covers the published research from 2000 to 2022. Moreover, the proposed mechanisms of Pd‐catalyzed annulation of Ugi adducts are also reviewed.

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“…For instance, the recent succinate dehydrogenase inhibitor (SDHI) fungicides pydiflumetofen, isoflucypram, and pyrapropoyne have pyrazole amide groups. Numerous biological activities can be performed by modifying the pyrazole scaffold, such as nematocidal [8][9][10], herbicidal [11,12], antimicrobial [13], antioxidant [14], fungicidal [15][16][17], anticancer [18], and insecticidal activities [19].…”

Section: Introductionmentioning

confidence: 99%

“…They were synthesized easily via five steps by using ethyl 4,4,4-trifluoro-3-oxobutanoate and triethyl orthoformate as starting materials. The synthesized compounds were characterized by 1 H NMR, 13 C NMR and HRMS. The compound 2-(benzylthio)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-1,3,4oxadiazole (5a) was further determined by X-ray single-crystal diffraction.…”

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confidence: 99%

Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoromethylpyrazoyl moiety

et al. 2022

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In order to find new lead compounds with high pesticidal activity, a series of 1,3,4-oxadiazole thioether compounds ( 5 series) were designed by using penthiopyrad as a synthon. They were synthesized easily via five steps by using ethyl 4,4,4-trifluoro-3-oxobutanoate and triethyl orthoformate as starting materials. The synthesized compounds were characterized by 1 H NMR, 13 C NMR and HRMS. The compound 2-(benzylthio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole ( 5a ) was further determined by X-ray single-crystal diffraction. It crystallized in the monoclinic system, space group P2 1 /c , Z = 4. All the 1,3,4-oxadiazole thioether derivatives were screened for fungicidal activity against ten fungi and herbicidal activity against two weeds. The bioassay results indicated that some of the synthesized 1,3,4-oxadiazole compounds exhibited good fungicidal activity (> 50% inhibition) against the plant pathogens Sclerotinia sclerotiorum and Rhizoctonia solani at 50 μg/mL. Some of them exhibited certain herbicidal activity, and compounds 2-((3-chlorobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole ( 5e) and 2-((4-bromobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole (5 g) had bleach effect. Molecular docking is to find the best fit orientation of the 2-((4-bromobenzyl)thio)-5-(1-methyl-3-(trifluoromethyl)-1 H -pyrazol-4-yl)-1,3,4-oxadiazole (5 g) molecule with the SDH protein (PDB: 2FBW). The docking results indicate that the compound 5 g and the lead compound penthiopyrad have similar binding interactions with SDH and carbonyl is a key group for these compounds. Supplementary Information The online version contains supplementary material available at 10.1007/s11164-022-04839-x.

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Pd-catalyzed post-Ugi intramolecular cyclization to the synthesis of isoquinolone-pyrazole hybrid pharmacophores & discover their antimicrobial and DFT studies

Cited by 11 publications

References 44 publications

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

Recent Applications of the Multicomponent Synthesis for Bioactive Pyrazole Derivatives

Annulation of the Ugi Products Using Palladium Catalysts

Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoromethylpyrazoyl moiety

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