Synthesis and Biological Evaluation of Novel Phenothiazine Derivatives as Potential Antitumor Agents

Kasi, Venkatesan; Satyanarayana, V. S. V.; Sivakumar, A.

doi:10.1080/10406638.2021.2021254

Cited by 9 publications

(7 citation statements)

References 36 publications

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“…This indicates the ability of 3-methyleneisoindolinone to disturb the cell cycle process, which was in consonance with previous findings of a similar category of anticancer compounds. 31 , 35 , 36 However, it was interesting to find that all the three leads arrest the cell cycle in different phases and could have a different mode of action on cancer cells. Additionally, a dose-dependent increase in the percentage of the cell population was observed in the Sub-G1 phase for 3n and 3h , indicating the presence of cellular apoptosis ( Figure 7 c,e).…”

Section: Resultsmentioning

confidence: 99%

Novel 3-Methyleneisoindolinones Diversified via Intramolecular Heck Cyclization Induce Oxidative Stress, Decrease Mitochondrial Membrane Potential, Disrupt Cell Cycle, and Induce Apoptosis in Head and Neck Squamous Cell Carcinoma Cells

et al. 2022

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Head and neck squamous cell carcinoma (HNSCC) is the sixth most prevalent cancer in the world and the most prevalent cancer of developing countries. Increased disease burden and a smaller number of approved targeted therapies are a growing concern worldwide. Isoindolinone motifs have been a central part of many pharmacological compounds, and their derivatives possess substantial anticancer potential. However, their anticancer potential against HNSCC has not been well investigated. In the current study, a series of 3-methyleneisoindolinones have been designed and synthesized and their late-stage intramolecular Heck cyclization was achieved to evaluate their anticancer potential against HNSCC cells. Additionally, in silico ADME profiling of synthesized compounds revealed their drug-likeness properties as potential drug candidates. Among the synthesized compounds, 3-bromo-5-methylpyridin-2-yl-3-methyleneisoindolin-1-one, i.e., 3n, with a pyridyl unit exhibited the most significant cytotoxicity against HNSCC cells. The cytotoxic potential of synthesized compounds varied depending on the nature of substituents present and has been well established with structure–activity relationship studies. Further, flow cytometric analysis showed that 3f, 3h, and 3n triggered intracellular oxidative stress, disrupted mitochondrial membrane potential, and interrupted the cell cycle of HNSCC cells in the S-phase and sub-G1 phase. Further, 3f, 3h, and 3n also exhibited pro-apoptotic potential and induced cellular apoptosis in the HNSCC cells. Overall, the findings of this study attributed 3-methyleneisoindolinone chemistry and efficacy evaluation and corroborated their anticancer potential against HNSCC. It will pave the way to further design and optimize novel 3-methyleneisoindolinone as effective antitumor agents, which may provide effective treatment modalities against HNSCC.

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Section: Resultsmentioning

confidence: 99%

Novel 3-Methyleneisoindolinones Diversified via Intramolecular Heck Cyclization Induce Oxidative Stress, Decrease Mitochondrial Membrane Potential, Disrupt Cell Cycle, and Induce Apoptosis in Head and Neck Squamous Cell Carcinoma Cells

et al. 2022

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“…2‐amino‐4 H ‐chromenes, 2‐amino‐4 H ‐benzopyrans, and spiroacenaphthylene derivatives have been synthesized by using highly effective catalyst Cu(bpdo) 2 ⋅ 2H 2 O] 2+ /montmorillonite [153] . N‐alkyl‐3‐formylphenothiazine under reflux/ultrasonic compound is synthesized in the laboratory, their result has been found as antitumor activities [154] . Singh obtained aromatic compounds from waste polystyrene, polyethylene, polypropylene plastics, which can be used in the medicinal field [155–160] .…”

Section: Benzopyran Derivatives Nomenclaturementioning

confidence: 99%

“…[153] Nalkyl-3-formylphenothiazine under reflux/ultrasonic compound is synthesized in the laboratory, their result has been found as antitumor activities. [154] Singh obtained aromatic compounds from waste polystyrene, polyethylene, polypropylene plastics, which can be used in the medicinal field. [155][156][157][158][159][160] Pagadala et al synthesized various heterocyclic compounds containing nitrogen, oxygen, and sulfur heteroatoms in a water solvent.…”

Section: Benzopyran Derivatives Nomenclaturementioning

confidence: 99%

Insights into the Origin and Therapeutic Implications of Benzopyran and Its Derivatives

Tiwari

Singh

2023

ChemistrySelect

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Benzopyran derivatives are essential for life and are found abundantly in nature. Benzopyran compounds and their derivatives play an essential role in medicinal chemistry. The alkaloids, flavonoids, tocopherols, and anthocyanins natural products comprise benzopyran's basic structure. Various benzopyran derivatives have been used for therapeutic effects. Benzopyran derivatives can be proficient in various pharmaceutical applications for cellular markers. The basic structure of benzopyran is an efficient class of synthetic products and an emerging attention area of research. Therefore, impactful information on benzopyran and its derivatives has been compiled in the last several years. Recently, the development of novel benzopyran and its applications are contributing to medicines and pharmacy.

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“…Phenothiazine-constructed dyes are advantageous as potential sensitizers for effective dye-sensitized solar cells because the molecular aggregation and the production of intermolecular excimers can be avoided since the phenothiazine ring is non-planar with butterfly confirmation in the ground state. [11][12] Chemical objects with the phenothiazine structural motif exhibit antibacterial, [13][14] antifungal, [15][16][17] antitubercular, [18] antioxidant, [19] antiplasmin, [20] anticancer, [21][22][23][24] antiinflammatory, [25] antiviral, [26] anticonvulsant, [27] antihistaminic, [28] antipsychotic [29] and anti-emetic activities. [30] Several recent research papers, book chapters, and articles have reviewed their notable characteristics.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Anticancer Molecular Docking Studies of Phenothiazine Derivatives – A Green Chemical Approach

Venkatesan,

Kumar,

Sivakumar

2023

ChemistrySelect

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Phenothiazines are antipsychotic drugs that have been studied for millennia. In addition to its fundamental neuroleptic properties, phenothiazines have attracted study attention for their anticancer properties. To develop powerful anticancer medications, we have concentrated on a variety of phenothiazine designs. In this study, we used a single step multicomponent reaction of N‐alkyl‐3‐formyl phenothiazine under reflux/ultrasonic conditions to produce a range of heterocyclic derivatives containing phenothiazine molecules. To characterize the structures of novel compounds, IR, 1H‐NMR, 13C‐NMR, and mass spectral data were utilized. Utilizing different cancer cell proteins, all the derivatives were investigated for their potential as anticancer molecules.

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Synthesis and Biological Evaluation of Novel Phenothiazine Derivatives as Potential Antitumor Agents

Cited by 9 publications

References 36 publications

Novel 3-Methyleneisoindolinones Diversified via Intramolecular Heck Cyclization Induce Oxidative Stress, Decrease Mitochondrial Membrane Potential, Disrupt Cell Cycle, and Induce Apoptosis in Head and Neck Squamous Cell Carcinoma Cells

Novel 3-Methyleneisoindolinones Diversified via Intramolecular Heck Cyclization Induce Oxidative Stress, Decrease Mitochondrial Membrane Potential, Disrupt Cell Cycle, and Induce Apoptosis in Head and Neck Squamous Cell Carcinoma Cells

Insights into the Origin and Therapeutic Implications of Benzopyran and Its Derivatives

Synthesis, Characterization and Anticancer Molecular Docking Studies of Phenothiazine Derivatives – A Green Chemical Approach

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