Designing, Synthesis, and Anti‐Breast Cancer Activity of a Series of New Quinazolin‐4(1<i>H</i>)‐one Derivatives

Reddy, Manne Madhava; Rajagopal, D.; Naik, Sanjay; Kumar, Sanjit; D, Thirumal Kumar; Doss, George C Priya; Sivaramakrishna, Akella

doi:10.1002/cbdv.202200662

Chemistry & Biodiversity

2022

DOI: 10.1002/cbdv.202200662

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Designing, Synthesis, and Anti‐Breast Cancer Activity of a Series of New Quinazolin‐4(1H)‐one Derivatives

Manne Madhava Reddy

D. Rajagopal

Sanjay Naik

et al.

Abstract: The inhibition of phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha (PIK3CA) protein could be a promising treatment for breast cancer. In this regard, docking studies were accomplished on various functionalized organic molecules. Among them, several derivatives of quinazolin-4(1H)-one exhibited anti-breast cancer activity and satisfied the drug likeliness properties. Further, the in vitro inhibitory studies by a series of 2-(2-phenoxyquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-one molecules… Show more

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Cited by 5 publications

References 46 publications

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A sustainable route toward the synthesis of highly substituted imidazole and quinoxaline derivatives using CuO@g‐C₃N₄ as an efficient and reusable heterogeneous catalyst

Gajurel

Sarkar

et al. 2023

Applied Organom Chemis

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This work demonstrates the preparation, characterization, and catalytic application of CuO@g‐C3N4 nanoparticles in synthesizing biologically and pharmaceutically important tetrasubstituted imidazole and quinoxaline derivatives. Highly substituted imidazoles of wide functionalities were synthesized in good yields (71%–85%) using EtOH as a solvent under refluxed conditions within 3–4 h. Similarly, a diverse range of quinoxaline derivatives were synthesized, which rendered moderate to good yield (65%–90%) of the products within 5–60 min in solvent‐free reaction conditions. The practical applicability of the developed protocol is shown by performing a gram‐scale reaction of quinoxaline. Furthermore, the reusability of the catalyst was studied up to the fifth consecutive cycle without much significant decrease in the activity of the catalyst. Additionally, the use of cheap metal and supported materials, shorter reaction time, high substrate scope, and easy recyclability of the catalyst are some of the salient features of the developed protocol.

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A sustainable route toward the synthesis of highly substituted imidazole and quinoxaline derivatives using CuO@g‐C₃N₄ as an efficient and reusable heterogeneous catalyst

Gajurel

Sarkar

et al. 2023

Applied Organom Chemis

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Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

et al. 2023

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Quinoline-based compounds are one of the most important classes of N-heterocyclics exhibiting a wide spectrum of biological activities. There is a constant demand for the synthesis of new quinoline-based molecules suitable for therapeutic applications. Here a new strategy is developed to synthesize different quinoline-based quinazolinones catalytically using InCl 3 through a cyclocondensation reaction of isatoic anhydride and aniline with 2-substituted-quinoline-3-carbaldehyde to produce 2-(2-phenoxyquinolin-3-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives (> 90 % yields). In contrast, the reduced electrophilicity at the metal center allows the hydrazide ligand to bind In(III) and serendipitously forms benzoic(2-phenoxyquinoline-3-carbonyl) carbamic anhydride (∼ 70 % yields). The mechanistic aspects of these reactions were rationally explained. The structure and purity of all the isolated derivatives were assessed by spectroscopic and analytical data. In view of a strong correlation existing between inflammation and cancer progression, the ex-vivo anti-inflammatory effect of the ligands was established. The anti-cancer property of the proposed ligand was delineated with a specific SIRT protein family. Further, the computational docking studies on the binding abilities of 22 synthesized compounds with the Sirt1 protein were discussed in detail.

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Cu(II)‐Catalyzed Green Synthesis of 1,4,5‐Trisubstituted‐1,2,3‐Triazoles from Chalcone Derivatives – Studies on Their Cytotoxicity Profile

Mondal,

Sivaramakrishna

2024

ChemistrySelect

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Triazoles are an important class of heterocyclic compounds due to their interesting structural features and versatile biological significance. In this regard, the present work highlights the synthesis of Cu(II)‐catalyzed 1,2,3‐trisubstituted triazoles through the cycloaddition of different chalcones with azides under neat methodology. A series of 16 triazole derivatives (3 a to 3 o) was prepared using 10 mol % Cu(II) complexes of 1,10‐phenanthroline and terpyridine‐based ligands as catalysts with moderate to excellent yields. All these derivatives were structurally analyzed by UV‐visible, infrared, 1H, 13C NMR and mass spectral data. The product, (4‐((4‐benzoyl‐5‐(4‐fluorophenyl)‐1H‐1,2,3‐triazol‐1‐yl) methyl)benzonitrile) (3 j) was structurally analyzed by single crystal XRD analysis. Also, the molecular structure of one of the catalysts, [Cu(Phen)2]2+(NO3−)2) was obtained by single crystal XRD analysis. Additional investigations of all these derivatives exhibited potential cytotoxic characteristics against MCF‐7 cancer cell lines. Among them, compounds 3 j, 3 i, 3 c, 3 d and 3 g facilitated the notable IC50 values. Moreover, the studies on the photophysical properties of synthesized derivatives showed the absorption bands in the range of 267–290 nm, depending on the nature of the substituent and the compounds 3 e and 3 f demonstrated the highest and lowest quantum yields as 0.05339 % and 0.01914 %, respectively.

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Designing, Synthesis, and Anti‐Breast Cancer Activity of a Series of New Quinazolin‐4(1H)‐one Derivatives

Cited by 5 publications

References 46 publications

A sustainable route toward the synthesis of highly substituted imidazole and quinoxaline derivatives using CuO@g‐C₃N₄ as an efficient and reusable heterogeneous catalyst

A sustainable route toward the synthesis of highly substituted imidazole and quinoxaline derivatives using CuO@g‐C₃N₄ as an efficient and reusable heterogeneous catalyst

Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

Cu(II)‐Catalyzed Green Synthesis of 1,4,5‐Trisubstituted‐1,2,3‐Triazoles from Chalcone Derivatives – Studies on Their Cytotoxicity Profile

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Designing, Synthesis, and Anti‐Breast Cancer Activity of a Series of New Quinazolin‐4(1H)‐one Derivatives

Cited by 5 publications

References 46 publications

A sustainable route toward the synthesis of highly substituted imidazole and quinoxaline derivatives using CuO@g‐C3N4 as an efficient and reusable heterogeneous catalyst

A sustainable route toward the synthesis of highly substituted imidazole and quinoxaline derivatives using CuO@g‐C3N4 as an efficient and reusable heterogeneous catalyst

Synthesis and Biological Evaluation of a Series of Quinoline‐Based Quinazolinones and Carbamic Anhydride Derivatives

Cu(II)‐Catalyzed Green Synthesis of 1,4,5‐Trisubstituted‐1,2,3‐Triazoles from Chalcone Derivatives – Studies on Their Cytotoxicity Profile

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Product

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A sustainable route toward the synthesis of highly substituted imidazole and quinoxaline derivatives using CuO@g‐C₃N₄ as an efficient and reusable heterogeneous catalyst

A sustainable route toward the synthesis of highly substituted imidazole and quinoxaline derivatives using CuO@g‐C₃N₄ as an efficient and reusable heterogeneous catalyst