ChemInform Abstract: NITRILE CYCLIZATION REACTIONS. VII. SYNTHESIS OF 6‐AMINO‐4‐ARYL‐3‐METHYL‐5‐CYANO‐1H,4H‐PYRAZOLO(3,4‐B)PYRANS

Sharanin, Yu. A.; Sharanina, L. G.; Puzanova, V. V.

doi:10.1002/chin.198414216

Cited by 7 publications

(4 citation statements)

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“…The synthesis of dihydropyrano[2,3- c ]pyrazole derivatives is getting tremendous attention among synthetic chemists for their diverse bioactivity profiles, − which include anticancer, anti-inflammatory, insecticidal, antimicrobial, and analgesic properties and Chk1 kinase inhibitory activity. Most of the synthetic endeavors to synthesize this bioactive core involve the multicomponent reaction of a mixture of aldehyde, malononitrile, ethyl acetoacetate, and hydrazine hydrate in the presence of environmentally noncompatible base catalysts − at elevated temperature. The use of a base catalyst at elevated temperature for such reactions has the potential to accomplish various side reactions such as Aldol condensation and the Cannizzaro reaction to generate unwanted byproducts.…”

Section: Introductionmentioning

confidence: 99%

Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles in Ethanol

Bihani

Bora

Bez

et al. 2013

ACS Sustainable Chem. Eng.

100

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Amberlyst A21 was found to be an extremely efficient catalyst for synthesis of a series of 6-amino-4-alkyl/ aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-carbonitriles by a four-component reaction of a mixture of ethyl acetoacetate, hydrazine hydrate, aldehyde, and malononitrile in ethanol at room temperature. The catalytic efficiency of Amberlyst A21 was compared with some other resin-bound free and anionic bases in order to ascertain the best catalyst for the said conversion. The catalyst was found to work extremely well also for acyclic/cyclic ketones to give corresponding dihydropyrano[2,3-c]pyrazoles or their spirocyclic variants. Easy recovery of the catalyst and its reusability, room temperature reaction conditions, short reaction time, excellent yields, no chromatographic purification, and evasion of environmentally hazardous solvents in the entire reaction process may make this protocol very useful for academia and industry.

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Section: Introductionmentioning

confidence: 99%

Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles in Ethanol

Bihani

Bora

Bez

et al. 2013

ACS Sustainable Chem. Eng.

100

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“…The most common and convenient approach towards diverse dihydropyrano[2,3- c ]pyrazoles is a two-step procedure ( Fig 2 ) comprising the following steps: (1) Condensation of hydrazine derivative 5 is condensensed with β-keto ester 6 under basic conditions to produce the 1 H -pyrazol-5(4 H )-one derivative 7 ; (2) Three-component base-catalyzed reaction of 1 H -pyrazol-5(4 H )-one 7 , aromatic aldehyde 8 and malononitrile 9 . The three-component reaction involve a tandem Michael addition-Thorpe-Ziegler-type reaction, followed by tautomerization [ 13 ] to generate the dihydropyrano[2,3- c ]pyrazole core 10 . It should be noted that these compounds may exist in the 1,4-dihydro or 2,4-dihydro tautomeric forms when the N1 position is unsubstituted (R 1 = H).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of dihydropyrano-[2,3-c]pyrazoles as a new class of PPARγ partial agonists

et al. 2017

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Peroxisome proliferator-activated receptor γ (PPARγ) is a well-known target for thiazolidinedione antidiabetic drugs. In this paper, we present the synthesis and biological evaluation of a series of dihydropyrano[2,3-c]pyrazole derivatives as a novel family of PPARγ partial agonists. Two analogues were found to display high affinity for PPARγ with potencies in the micro molar range. Both of these hits were selective against PPARγ, since no activity was measured when tested against PPARα, PPARδ and RXRα. In addition, a novel modelling approach based on multiple individual flexible alignments was developed for the identification of ligand binding interactions in PPARγ. In combination with cell-based transactivation experiments, the flexible alignment model provides an excellent analytical tool to evaluate and visualize the effect of ligand chemical structure with respect to receptor binding mode and biological activity.

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“…Synthesis of dihydropyrano[2,3- c ]pyrazoles can be achieved by various methodologies. Several catalysts including trimethylamine [ 25 , 26 , 27 ], piperazine [ 28 ], piperidine [ 29 ], N -methylmorpholine [ 30 ], heteropolyacids [ 31 ], glycine [ 32 ], per-6-amino-β-cyclodextrin [ 33 ], Mg/Al hydrotalcite [ 34 ], nanosized magnesium oxide [ 35 ], L-proline [ 36 ], γ-alumina [ 37 ], sodium benzoate [ 38 ], Amberlyst A21 [ 39 ] and CTACl [ 40 ], [Bmim]BF 4 [ 41 ], PS-PTSA [ 42 ], urea [ 43 ] and ethanol and water (1:1) [ 44 ] are reported in the literature. Ionic liquids have gained importance as green solvent for organic transformations [ 45 , 46 , 47 ] due to their special properties, including good solvating capability, negligible vapor pressure, non-inflammable, ease of recyclability, controlled miscibility and high thermal stability [ 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

Nimbalkar¹,

Seijas

Vázquez-Tato

et al. 2017

Molecules

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A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles 5a–j were synthesized via one-pot, four-component condensation reactions of aryl aldehydes 1a–j, propanedinitrile (2), hydrazine hydrate (3) and ethyl acetoacetate (4) under solvent-free conditions. We report herein the use of the Brønsted acid ionic liquid (BAIL) triethylammonium hydrogen sulphate [Et3NH][HSO4] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2), breast cancer cell line(MDA-MB-231), leukemia cancer cell line (K-562) and cervical cancer cell line (HeLa). Compounds 5b, 5d, 5g, 5h and 5j exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed 5b and 5d as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and non-toxic nature.

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ChemInform Abstract: NITRILE CYCLIZATION REACTIONS. VII. SYNTHESIS OF 6‐AMINO‐4‐ARYL‐3‐METHYL‐5‐CYANO‐1H,4H‐PYRAZOLO(3,4‐B)PYRANS

Abstract: Aus aromatischen Aldehyden und Malodinitril werden die Arylidenmalodinitrile (I) dargestellt.

Cited by 7 publications

References 0 publications

Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles in Ethanol

Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles in Ethanol

Synthesis and biological evaluation of dihydropyrano-[2,3-c]pyrazoles as a new class of PPARγ partial agonists

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

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