Quinoxaline as a potent heterocyclic moiety

Srivastava, S D; Banerjee, Janmajoy; Srestha, Nomi

doi:10.9790/3013-040120101617027

Cited by 4 publications

(4 citation statements)

References 13 publications

(7 reference statements)

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“…In this study, the four quinoxaline derivatives were designed to possess the signature benzopyrazine core molecule made of a benzene ring and a pyrazine ring capable of triggering antimicrobial activities and induce anticancer properties due to their ability to bind DNA [31,32]. Four slight variations were made on the side chains attached to the benzopyrazine core group.…”

Section: Methodsmentioning

confidence: 99%

Induction of Cell Death in Human A549 Cells Using 3-(Quinoxaline-3-yl) Prop-2-ynyl Methanosulphonate and 3-(Quinoxaline-3-yl) Prop-2-yn-1-ol

et al. 2019

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Despite major advancements in the development of various chemotherapeutic agents, treatment for lung cancer remains costly, ineffective, toxic to normal non-cancerous cells, and still hampered by a high level of remissions. A novel cohort of quinoxaline derivatives designed to possess a wide spectrum of biological activities was synthesized with promising targeted and selective anticancer drug activity. Hence, this study was aimed at determining in vitro anticancer activity effects of a newly synthesized class of 3-(quinoxaline-3-yl) prop-2-ynyl quinoxaline derivatives on A549 lung cancer cells. An assessment of the quinoxaline derivatives ferric reducing power, free radical scavenging activity, cytotoxic activity, and ability to induce reactive oxygen species (ROS) production was performed using the Ferric Reducing Antioxidant Power (FRAP), 2,2-diphenyl-1-picryl-hydrazyl (DPPH), 3-[4,5-dimethylthiazole-2-yl]-2,5-diphenyltetrazolium bromide (MTT) and 2’,7’-dichlorodihydrofluorescein diacetate (H2DCFDA) assays, respectively. The ability of the quinoxaline derivatives to induce apoptosis in A549 cells was assessed using the Acridine Orange/Ethidium Bromide (AO/EB) and Annexin V-FITC/Dead Cell Assay. Of the four quinoxaline derivatives tested, 3-(quinoxaline-3-yl) prop-2-ynyl methanosulphate (LA-39B) and 3-(quinoxaline-3-yl) prop-2-yn-1-ol (LA-55) displayed a dose-dependent reducing power, free-radical scavenging activity, inhibition of cell viability, and stimulation of ROS production which was accompanied by induction of apoptosis in A549 lung cancer cells. None of the quinoxaline derivatives induced cell death or ROS production in non-cancerous Raw 267.4 macrophage cells. Cytotoxicity was observed in A549 lung cancer, HeLa cervical cancer, and MCF-7 breast cancer cells albeit inhibition was more pronounced in A549 cells. The results of the study suggest that 3-(quinoxaline-3-yl) prop-2-ynyl methanosulphate and 3-(quinoxaline-3-yl) prop-2-yn-1-ol induce apoptotic cell death in A549 lung cancer cells.

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Section: Methodsmentioning

confidence: 99%

Induction of Cell Death in Human A549 Cells Using 3-(Quinoxaline-3-yl) Prop-2-ynyl Methanosulphonate and 3-(Quinoxaline-3-yl) Prop-2-yn-1-ol

et al. 2019

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“…In quinoxaline, two benzene rings combine, expanding the variety of resonance structures available to these systems. It possesses a zero-dipole moment [ 246 ]. Due to the wide range of pharmacological activities that quinoxalines exhibit, they have received a lot of interest.…”

Section: Current Advances In Nitrogen Containing Heterocycles As Anti...mentioning

confidence: 99%

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Kumar

Singh

et al. 2023

Pharmaceuticals

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Cancer is one of the major healthcare challenges across the globe. Several anticancer drugs are available on the market but they either lack specificity or have poor safety, severe side effects, and suffer from resistance. So, there is a dire need to develop safer and target-specific anticancer drugs. More than 85% of all physiologically active pharmaceuticals are heterocycles or contain at least one heteroatom. Nitrogen heterocycles constituting the most common heterocyclic framework. In this study, we have compiled the FDA approved heterocyclic drugs with nitrogen atoms and their pharmacological properties. Moreover, we have reported nitrogen containing heterocycles, including pyrimidine, quinolone, carbazole, pyridine, imidazole, benzimidazole, triazole, β-lactam, indole, pyrazole, quinazoline, quinoxaline, isatin, pyrrolo-benzodiazepines, and pyrido[2,3-d]pyrimidines, which are used in the treatment of different types of cancer, concurrently covering the biochemical mechanisms of action and cellular targets.

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“…(iv) 3-Hydrazinoquinoxaline (10) was also used in earlier microwave assisted organic synthesis (MAOS) to validate its facile condensation with 1,3-diketone and β-keto ester to produce 3-(3,5-disubstituted-1H-pyrazol-1-yl)quinoxalin-2(1H)-one (14) and 3-(3-substituted-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)quinoxalin-2(1H)-one (15), resp., as shown in Scheme 4 (87,89). (v) Design of a method essential for the synthesis of a quinoxaline-based candidate via the one-pot approach using [2-(sulfooxy)ethyl]sulfuric acid (SESA) was achieved as shown in Scheme 5 (90).…”

Section: Synthesis Of Quinoxaline and Its Derivativesmentioning

confidence: 99%

Chemistry and pharmacological diversity of quinoxaline motifs as anticancer agents

et al. 2019

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Surpassing heart diseases, cancer is taking the lead as the deadliest disease because of its fast rate of spreading in all parts of the world. Tireless commitment to searching for novel therapeutic medicines is a worthwhile adventure in synthetic chemistry because of the drug resistance predicament and regular outbreak of new diseases due to abnormal cell growth and proliferation. Medicinal chemistry researchers and pharmacists have unveiled quinoxaline templates as precursors of importance and valuable intermediates in drug discovery because they have been established to possess diverse pharmacological potentials. Hence, this review highlights the current versatile routes to accessing functionalized quinoxaline motifs and harnessing their documented therapeutic potentials for anticancer drug development.

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Quinoxaline as a potent heterocyclic moiety

Abstract: Various novel, mild, eco-

Cited by 4 publications

References 13 publications

Induction of Cell Death in Human A549 Cells Using 3-(Quinoxaline-3-yl) Prop-2-ynyl Methanosulphonate and 3-(Quinoxaline-3-yl) Prop-2-yn-1-ol

Induction of Cell Death in Human A549 Cells Using 3-(Quinoxaline-3-yl) Prop-2-ynyl Methanosulphonate and 3-(Quinoxaline-3-yl) Prop-2-yn-1-ol

Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective

Chemistry and pharmacological diversity of quinoxaline motifs as anticancer agents

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