Synthesis, docking study, and DNA photocleavage activity of some pyrimidinyl hydrazones and 3-(quinolin-3-yl)-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidine derivatives

Sharma, Ajay; Kumar, Vinod; Khare, Rajshree; Gupta, Girish Kumar; Beniwal, Vikas

doi:10.1007/s00044-014-1265-9

Cited by 18 publications

(8 citation statements)

References 35 publications

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“…The agarose gel electrophoresis is based on the principle that supercoiled DNA (Form I) migrates faster than open circular (Form II) (in which one strand is nicked). The linear form (Form III), the migrating form between Forms I and II, will be produced upon the cleavage of both strands [105] . Extensive double‐strand breaks lead to DNA degradation [106] .…”

Section: Resultsmentioning

confidence: 99%

“…The linear form (Form III), the migrating form between Forms I and II, will be produced upon the cleavage of both strands. [105] Extensive double-strand breaks lead to DNA degradation. [106] All compounds were found to be inactive and non-toxic in the absence of light, demonstrating that light is required to cause significant damage to the supercoiled plasmid DNA.…”

Section: Dna Photocleavage Studiesmentioning

confidence: 99%

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Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Ragheb

Abdelwahab

Darweesh

et al. 2022

Chemistry & Biodiversity

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The cyclocondensation reaction of aldehydes with dimedone and bis(6-aminopyrimidin-4-one) in acetic acid led to the formation of the corresponding bis (pyrimido[4,5-b]quinoline-4,6-diones) which are known as bis(sulfanediyl)bis(tetrahydro-5-deazaflavin) analogs in a single step. Also, bis(pyrimido[4,quinoline-4,6diones) which are linked to naphthyl core via phenoxymethyl linkage is prepared. The interactions of the synthesized compounds with DNA and bovine serum albumin (BSA) were studied. Gel electrophoresis assay was used to show the capability of the compounds to photocleave the supercoiled pBR322 plasmid DNA in UV-A (365 nm). Besides, the most photocleavable compound, bis(tetrahydropyrimido[4,5-b]quinoline-4,6-dione) linked to pyridin-3-yl at position-5 exhibits good binding affinities toward CT-DNA and BSA as supported by UV/VIS spectral studies. In addition to the experimental findings, a molecular docking simulation was performed to collect detailed binding data for this compound to both biomolecules.

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Section: Resultsmentioning

confidence: 99%

Section: Dna Photocleavage Studiesmentioning

confidence: 99%

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Ragheb

Abdelwahab

Darweesh

et al. 2022

Chemistry & Biodiversity

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“…Amongst the compounds, 25 and 26 resulted in maximum DNA photocleavage activity at 40 μg/ml concentration and they can convert the supercoiled form of DNA into an open circular form. Molecular docking results depicted that compounds 25 (binding energy=−82.76 kcal/mol) and 26 (binding energy=−80.32 kcal/mol) showed the highest interaction with targeted DNA gyrase A enzyme among the synthesized derivatives [84] …”

Section: Quinoline Hydrazide/hydrazone Derivatives As Antibacterial A...mentioning

confidence: 99%

Quinoline Hydrazide/Hydrazone Derivatives: Recent Insights on Antibacterial Activity and Mechanism of Action

et al. 2023

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Antibiotics are becoming gradually ineffective due to drug resistance, leading to greater difficulty in the treatment of infectious diseases. Therefore, the development of new chemical entities with different mechanisms of action is essential in the fight against resistant microorganisms. Various studies have shown that quinoline hydrazide/hydrazone derivatives possess several biological activities, such as antimalarial, antitubercular, anticancer, anti-inflammatory, and antimicrobial. Among these activities, the antibacterial activity of quinoline hydrazide/ hydrazone derivatives is noteworthy. The synthetic flexibility of the quinoline ring has led to the development of a wide range of structurally diverse quinoline hydrazide/hydrazone derivatives, which can act at various bacterial targets such as DNA gyrase, glucosamine-6-phosphate synthase, enoyl ACP reductase, and 3-ketoacyl ACP reductase. This review emphasizes the antibacterial potential of various reported quinoline hydrazide/ hydrazone derivatives based on substitution in the quinoline ring. The antibacterial activity of various metal-quinoline hydrazide/hydrazone complexes is also discussed. The aim of this review is to assemble and scrutinize the latest reports in this promising area of drug development.

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“…The IBD-mediated oxidative cyclization of new pyrimidinylhydrazoned erivatives was reported by Sharma et al The reaction of 2-hydrazino-4,6-dimethylpyrimidine with substituted 2-chloroquinoline-3-carbaldehydes in the presence of H 2 SO 4 at reflux in EtOH afforded the pyrimidinylhydrazoned erivatives, which were treated with iodobenzenediacetate in CH 2 Cl 2 at room temperature for 1hour to obtain triazolopyrimidine derivatives (Scheme 13). [46] 4. Fused 1,2,4-Triazolo[4,3-a]quinolines 3-a]quinolines were obtained by the oxidation of 2-quinolylhydrazones with IBD in CH 2 Cl 2 (Scheme 14).…”

Section: -Chloro-8-bromo-3-aryl-[124]-triazolo[43-c]pyrimidinesmentioning

confidence: 99%

Hypervalent‐Iodine(III)‐Mediated Oxidative Methodology for the Synthesis of Fused Triazoles

Kamal

Kumar

2016

Chemistry An Asian Journal

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The organic chemistry of hypervalent organoiodine compounds has been an area of unprecedented development. This surge in interest in the use of hypervalent iodine compounds has mainly been owing to their highly selective oxidizing properties, environmentally benign character and commercial availability. Hypervalent iodine reagents have also been used as an alternative to toxic heavy metals, owing to their low toxicity and ease of handling. Hypervalent organoiodine(III) reagents are versatile oxidants that have been successfully employed to extend the scope of selective oxidative transformations of complex organic molecules in synthetic chemistry. This Focus Review concerns the tandem in situ generation and 1,5-electrocyclization of N-heteroaryl nitrilimines into fused triazoles. We describe the importance of recently developed hypervalent-organoiodine(III)-catalyzed oxidative cyclization reactions, building towards the conclusion that hypervalent iodine chemistry is a promising frontier for oxidative cyclization, in particular of hydrazones, for the synthesis of fused triazoles.

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Synthesis, docking study, and DNA photocleavage activity of some pyrimidinyl hydrazones and 3-(quinolin-3-yl)-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidine derivatives

Cited by 18 publications

References 35 publications

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Quinoline Hydrazide/Hydrazone Derivatives: Recent Insights on Antibacterial Activity and Mechanism of Action

Hypervalent‐Iodine(III)‐Mediated Oxidative Methodology for the Synthesis of Fused Triazoles

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