Synthesis, characterization, antibacterial and DNA photocleavage study of 1-(2-Arenethyl)-3, 5-dimethyl-1H-pyrazoles

Sharma, Tulika; Vinit,; Sakshi, .; Bawa, Shubham; Kumar, Vikas; Singh, Joginder; Kataria, Ramesh; Singh, Bijender; Kumar, Vinod

doi:10.1016/j.cdc.2020.100408

Cited by 5 publications

(3 citation statements)

References 13 publications

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“…Certainly, since none of the compounds was tested for photosensitivity by itself but as a DNA complex, the phenomenon is much more complex. Nonetheless, the bromine atom in this position may contribute to a high atom effect in the photochemistry of the compound [42,46,47].…”

Section: Dna Photo-cleavage Experiments At 365 Nm (Uv-a Irradiation)mentioning

confidence: 99%

“…However, the interest for small organic molecules that can photocleave DNA [37] is showing a come-back due to the need for alternative anticancer and antimicrobial therapies able to overcome drug resistances [38][39][40][41]. Thus, pyrazoles (UV-A), trifluoromethyl pyrazolines and pyrazoles (UV-B), as well as bis-pyranopyrazoles (UV-A), were found to photocleave DNA exhibiting additional antibacterial, cytotoxic and antimicrobial activities, respectively [42][43][44]. Interestingly, halogenated derivatives were the best photocleavers among pyrazoles [42], as well as nitro-substituted trifluoromethyl pyrazoles [43].…”

Section: Introductionmentioning

confidence: 99%

“…Thus, pyrazoles (UV-A), trifluoromethyl pyrazolines and pyrazoles (UV-B), as well as bis-pyranopyrazoles (UV-A), were found to photocleave DNA exhibiting additional antibacterial, cytotoxic and antimicrobial activities, respectively [42][43][44]. Interestingly, halogenated derivatives were the best photocleavers among pyrazoles [42], as well as nitro-substituted trifluoromethyl pyrazoles [43]. Deazaflavin analogs linked to the naphthalene core (UV-A) [45] were also found to photocleave DNA, and quinolinium dicarbocyanine dyes (near IR) bearing a pentamethine bridge that was meso-substituted with halogen caused photodynamic cell damage [46,47].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2-Amino-N′-aroyl(het)arylhydrazides, DNA Photocleavage, Molecular Docking and Cytotoxicity Studies against Melanoma CarB Cell Lines

Mitrakas,

Stathopoulou,

Mikra

et al. 2024

Molecules

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Diacylhydrazine bridged anthranilic acids with aryl and heteroaryl domains have been synthesized as the open flexible scaffold of arylamide quinazolinones in order to investigate flexibility versus rigidity towards DNA photocleavage and sensitivity. Most of the compounds have been synthesized via the in situ formation of their anthraniloyl chloride and subsequent reaction with the desired hydrazide and were obtained as precipitates, in moderate yields. All compounds showed high UV-A light absorption and are eligible for DNA photocleavage studies under this “harmless” irradiation. Despite their reduced UV-B light absorption, a first screening indicated the necessity of a halogen at the p-position in relation to the amine group and the lack of an electron-withdrawing group on the aryl group. These characteristics, in general, remained under UV-A light, rendering these compounds as a novel class of UV-A-triggered DNA photocleavers. The best photocleaver, the compound 9, was active at concentrations as low as 2 μΜ. The 5-Nitro-anthranilic derivatives were inactive, giving the opposite results to their related rigid quinazolinones. Molecular docking studies with DNA showed possible interaction sites, whereas cytotoxicity experiments indicated the iodo derivative 17 as a potent cytotoxic agent and the compound 9 as a slight phototoxic compound.

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Section: Dna Photo-cleavage Experiments At 365 Nm (Uv-a Irradiation)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2-Amino-N′-aroyl(het)arylhydrazides, DNA Photocleavage, Molecular Docking and Cytotoxicity Studies against Melanoma CarB Cell Lines

Mitrakas,

Stathopoulou,

Mikra

et al. 2024

Molecules

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An expeditious one pot green synthesis of novel bioactive 1, 4-dihydropyridine derivatives at ambient temperature and molecular modelling

Gandhare

Ali

et al. 2021

Current Research in Green and Sustainable Chemistry

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Methyl-linked Pyrazoles: Synthetic and Medicinal Perspective

Sharma

Singh

et al. 2022

MRMC

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: Pyrazoles, an important and well known class of the azole family, have been found to show a large number of applications in various fields specially of medicinal chemistry. Among pyrazole derivatives, particularly, methyl substituted pyrazoles have been reported as the potent medicinal scaffolds that exhibit a wide spectrum of biological activities. The present review is an attempt to highlight the detailed synthetic approaches for methyl substituted pyrazoles along with in depth analysis of their respective medical significances till March2021. It is hoped that literature sum-up in the form of present review article would certainly be a great tool to assist the medicinal chemists for generating new leads possessing pyrazole nucleus with high efficacy and less microbial resistance.

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Synthesis, characterization, antibacterial and DNA photocleavage study of 1-(2-Arenethyl)-3, 5-dimethyl-1H-pyrazoles

Cited by 5 publications

References 13 publications

Synthesis of 2-Amino-N′-aroyl(het)arylhydrazides, DNA Photocleavage, Molecular Docking and Cytotoxicity Studies against Melanoma CarB Cell Lines

Synthesis of 2-Amino-N′-aroyl(het)arylhydrazides, DNA Photocleavage, Molecular Docking and Cytotoxicity Studies against Melanoma CarB Cell Lines

An expeditious one pot green synthesis of novel bioactive 1, 4-dihydropyridine derivatives at ambient temperature and molecular modelling

Methyl-linked Pyrazoles: Synthetic and Medicinal Perspective

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