Nickel nanoparticles: a highly efficient and retrievable catalyst for the solventless Friedlander annulation of quinolines and their in silico molecular docking studies as histone deacetylase inhibitors

Angajala, Gangadhara; Subashini, R.

doi:10.1039/c5ra06593c

Cited by 21 publications

(8 citation statements)

References 74 publications

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“…The synthesis of polysubstituted quinolines by the reaction of 2-aminoaryl ketone with enolizable ketone in the presence of nickel nano catalyst was already reported in our previous work [14] (Scheme.1) ( Fig.1). The binding affinity of polysubstituted quinoline analogues (1a-g) with PPARγ were analyzed by using Autodock.v.1.5.6.…”

Section: A Synthesis Of Polysubstituted Quinolinesmentioning

confidence: 80%

Molecular Modelling and in Vitro Hypoglycemic Examination of Polysubstituted Quinoline Derivatives

Angajala¹,

Aruna²,

Subashini³

et al. 2019

IJEAT

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In the present work in-silico molecular simulations were carried out to find out the binding affinities of synthesized polysubstituted quinolines towards PPARγ protein (2XKW). The results obtained from docking analysis showed that the synthesized polysubstituted quinoline derivatives 1a-g are having stronger binding interactions which was on par to that of standards rosiglitazone and pioglitazone. In addition to this in-vitro hypoglycemic studies were studied through α-amylase and α-glucosidase enzyme inhibition assays. The results showed that compounds 1c and 1d possess good hypoglycemic efficacy with percentage inhibition of 87.94 ± 0.25, 85.90 ± 0.56 towards α-glucosidase and 84.55 ± 1.02, 82.14 ± 0.26 percent inhibition towards α-amylase which was greater than standard rosiglitazone and comparable to standard pioglitazone

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Section: A Synthesis Of Polysubstituted Quinolinesmentioning

confidence: 80%

Molecular Modelling and in Vitro Hypoglycemic Examination of Polysubstituted Quinoline Derivatives

Angajala¹,

Aruna²,

Subashini³

et al. 2019

IJEAT

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“…Several methods must be highlighted for the Friedländer synthesis of quinolones under conventional conditions, all regarding the use of heterogeneous and recyclable catalysts. Fe 3 O 4 @SiO 2 -imid-PMA n , Ni NPs, sulfamic acid and nanoflake ZnO catalysts have all presented great yields in solvent-free conditions for a great variety of substituents. Moreover, the first three methods were performed in short reaction times (under 1 h) and required only 5%–10% mol of catalyst to reach full catalytic activity.…”

Section: Nonenergy Efficient Green Reactionsmentioning

confidence: 99%

Synthesis of Quinolines: A Green Perspective

Batista

Pinto

Silva

2016

ACS Sustainable Chem. Eng.

115

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The quinoline scaffold is present in a vast number of natural compounds and pharmacologically active substances, comprising a significant segment of the pharmaceutical market. The classical methods for the synthesis of this heterocyclic skeleton require the use of expensive starting materials and high temperature conditions. Chemists play a fundamental role in the construction of a sustainable future through the pursuit of greener chemical processes. As so, the development of new synthetic methods using more efficient energy sources and less hazardous solvents as well as renewable and eco-friendly catalysts to attain the quinoline scaffold can provide significant environmental and economic advantages. This review unveils green methods used in the synthesis of quinolones. Important green metrics are calculated for each proposed method and the statistical analysis allowed us to propose the best approaches for further investigation. The applied research is eventually unveiling the full potential of Friedländer and/or multicomponent reactions, to improve atom economy. The quinoline structural motif is readily available through a number of classical synthetic routes and from commercially available reagents. The Friedländer synthetic method (A) from ortho-aminoacetophenones (10) and the Skraup (B), Combes (D) and Doebner-Miller (F) syntheses from anilines (11), as well as its adaptations, are good examples. Moreover, the Conrad-Limpach (C), Gould-Jacobs (E) and Camps (G) routes for the synthesis of quinolones are widely used methods (Scheme 1). Still, all classical methods have similar disadvantages, requiring highly acidic and/or oxidizing media, high temperatures and long reaction times.Moreover, most of these synthetic routes present selectivity problems with meta-substituted substrates and its versatility is limited by the reactivity of the methylenic carbon involved in the aldol reaction. 19 Although efficient and versatile, classical routes towards the synthesis of quinolines present serious environmental concerns as most synthetic routes use great excess of a reagents and produce a significant amount of toxic waste.

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“…In literature, various methods are reported for Friedlander condensation using nanoparticles such as calcium silicate [41], nickel nanocomposite [42,43], while zinc titanate was used for one‐pot three‐component synthesis [44]. Metal oxides are extensively employed in the field of heterogeneous catalysis because they provide large surface area and active sites to adsorb the substrate.…”

Section: Introductionmentioning

confidence: 99%

New synthetic strategy for Friedlander condensation of 4‐amino‐2‐oxo‐2H‐chromene‐3‐carbaldehyde by heterogeneous catalysis

Jadhav¹,

Medhane²,

Deshmukh³

et al. 2021

Journal of Heterocyclic Chem

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Chromenopyridines are an important class of compound because of their diverse biological activities. In the present work, we have developed convenient route for the synthesis of chromeno[4,3‐b] pyridine derivatives (3a–e, 5a–e, and 7a–d) by Friedlander condensation of 4‐amino‐2‐oxo‐2H‐chromene‐3‐carbaldehyde with various active methylene compounds. We have used mixed metal oxide catalyst such as nanomaterial Zinc titanate. The reaction was carried out for various solvent systems, also we have altered the concentration of the catalyst. The 2‐propanol/water solvent system and 5 mol% catalyst concentration are best as far as yield and rate of reaction are concerned. The structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectra, and elemental analysis.

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Nickel nanoparticles: a highly efficient and retrievable catalyst for the solventless Friedlander annulation of quinolines and their in silico molecular docking studies as histone deacetylase inhibitors

Abstract: Highly efficient, solvent-free protocol for the synthesis of polysubstituted quinolines via Friedlander annulation using nickel nanoparticles from Aegle Marmelos Correa aqueous leaf extract.

Cited by 21 publications

References 74 publications

Molecular Modelling and in Vitro Hypoglycemic Examination of Polysubstituted Quinoline Derivatives

Molecular Modelling and in Vitro Hypoglycemic Examination of Polysubstituted Quinoline Derivatives

Synthesis of Quinolines: A Green Perspective

New synthetic strategy for Friedlander condensation of 4‐amino‐2‐oxo‐2H‐chromene‐3‐carbaldehyde by heterogeneous catalysis

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