Antibacterial Evaluation of Benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines, Pyrazolo[3,4- b]pyrido-[2',3'-b]-1,6-naphthyridines and Dipyrazolo[3,4-b];3',4'-h]-1,6-naphthyridines

Khakwani, Samia; Aslam, Samina; Shahi, Mehrzadi Noureen; Mussadiq, Sara; Bernardino, Alice M. R.; Khan, Misbahul Ain

doi:10.14233/ajchem.2017.19984

Cited by 5 publications

(3 citation statements)

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“…Pyrazole is another notable N -heterocyclic compound found in a variety of natural and synthetic molecules with innumerable applications . Pyrazole fused with other bioactive moieties such as naphthyridine exhibit anti-HSV-1, antibacterial, and acetylcholinesterase inhibition properties. Representative examples of some bioactive naphthyridine derivatives and our product are shown in Figure .…”

Section: Introductionmentioning

confidence: 99%

Domino Reaction for the Synthesis of Pyrazole/Isoxazole Fused Naphthyridine Derivatives Involving Indole Ring Opening and Double Ring Formation

Darakshan

Parvin

2023

J. Org. Chem.

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Herein, a hitherto unreported approach for the synthesis of pyrazole/isoxazole-fused naphthyridine derivatives by a three-component domino reaction of arylglyoxal monohydrate, 5-amino pyrazole/isoxazole, and indoles in acetic acid medium has been reported. In this method, four bonds (2 C–C and 2 C–N) form in one-pot with the concomitant formation of two new pyridine rings via indole ring opening and double cyclization reactions. This methodology is also applicable in gram-scale synthesis. The reaction mechanism was studied by isolating and characterizing the reaction intermediates. Along with complete characterization of all the products, the structure of the product 4o was unambiguously confirmed by single crystal X-ray diffraction.

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Section: Introductionmentioning

confidence: 99%

Domino Reaction for the Synthesis of Pyrazole/Isoxazole Fused Naphthyridine Derivatives Involving Indole Ring Opening and Double Ring Formation

Darakshan

Parvin

2023

J. Org. Chem.

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“…1,6-Naphthyridines have received considerable attention because of their wide range of biological activities, 1–3 including antitumor, anti-inflammatory, antimicrobial, 4 and anticonvulsant. Both pyrimidine and 1,6-naphthyridine scaffolds have been shown to be important structural motifs in chemistry; therefore, the preparation of pyrimidonaphthyridine derivatives, in which these scaffolds are merged, might provide compounds that exhibit simultaneously the biological properties of each moiety.…”

Section: Introductionmentioning

confidence: 99%

“…Both pyrimidine and 1,6-naphthyridine scaffolds have been shown to be important structural motifs in chemistry; therefore, the preparation of pyrimidonaphthyridine derivatives, in which these scaffolds are merged, might provide compounds that exhibit simultaneously the biological properties of each moiety. 4–6…”

Section: Introductionmentioning

confidence: 99%

Preparation of pyrimido[4,5-b][1,6]naphthyridin-4(1H)-one derivatives using a zeolite–nanogold catalyst and their in vitro evaluation as anticancer agent

Eid

Hassaneen

Loutfy

et al. 2021

Journal of Chemical Research

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Catalysis using supported gold nanoparticles has attracted significant research interest due to their unique properties and potential that is directly related to their particle size. An efficient one-pot, three-component procedure is developed for the preparation of pyrimido[4,5- b][1,6]naphthyridin-4( 1H)-one derivatives (4a–h) by cyclocondensation of 6-amino-2-thioxo-2,3-dihydropyrimidin-4( 1H)-one (1), aromatic aldehydes (2), and 1-benzylpiperidin-4-one (3) in the presence of zeolite-nano Au as a green catalyst in ethanol at 80 °C. The presented methodology has a number of advantages including a reusable catalyst, easy access, short reaction times, high yields, and an easy work-up. The nanogold catalyst is characterized by X-ray diffraction and transmission electron microscopy. The structures of the prepared compounds are established by elemental analyses and spectral data (infrared, mass spectrometry, 1H, and 13C NMR). While molecular docking studies show that products 4a and 4c have binding affinities with the active site of CDKs. A bio-evaluation assay revealed that some of the products exhibit strong to moderate effects against proliferation of Huh7 in an in vitro model of human liver cancer cells as confirmed by morphological alteration. Compounds 4c and 4a offer the lowest IC50 values at 22.5 and 39 µM, respectively.

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Synthesis and Anticancer Properties of Functionalized 1,6-Naphthyridines

et al. 2021

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Antibacterial Evaluation of Benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines, Pyrazolo[3,4- b]pyrido-[2',3'-b]-1,6-naphthyridines and Dipyrazolo[3,4-b];3',4'-h]-1,6-naphthyridines

Cited by 5 publications

References 0 publications

Domino Reaction for the Synthesis of Pyrazole/Isoxazole Fused Naphthyridine Derivatives Involving Indole Ring Opening and Double Ring Formation

Domino Reaction for the Synthesis of Pyrazole/Isoxazole Fused Naphthyridine Derivatives Involving Indole Ring Opening and Double Ring Formation

Preparation of pyrimido[4,5-b][1,6]naphthyridin-4(1H)-one derivatives using a zeolite–nanogold catalyst and their in vitro evaluation as anticancer agent

Synthesis and Anticancer Properties of Functionalized 1,6-Naphthyridines

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