Efficient Synthesis of RuO<sub>2</sub> Nanoparticle with excellent activity for one‐pot Synthesis of 2,3‐disubstituted quinazolin‐4(1H)‐ones

Raghu, M.S.; Prasad, K. N. N.; Jayanna, B.K.; Kumar, C.B. Pradeep; Kumar, K. Yogesh; Prashanth, M.K.

doi:10.1002/vjch.201900092

Cited by 12 publications

(2 citation statements)

References 24 publications

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“…As a context for this investigation and in keeping with our interest in bioactive compound synthesis, [ 20–28 ] we report here the microwave synthesis of tertiary amines through N ‐alkylation of amines with alcohols using MnCl 2 as a catalyst. All of the newly synthesized compounds were tested in vitro against the A549, MCF7, MDA‐MB‐231, HT‐29, and HCT116 cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted N‐alkylation of amines with alcohols catalyzed by MnCl₂: Anticancer, docking, and DFT studies

Kumar

Kumar²,

Prasad³

et al. 2022

Archiv der Pharmazie

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A new protocol for the N‐alkylation of amines with alcohols for the synthesis of tertiary amines in the presence of MnCl2 as a catalyst, under microwave conditions, is described. The advantages of this protocol include stable reaction profiles, a wide substrate variety, excellent yields, low cost, high yields, and easy workup conditions. The anticancer efficacy of all the synthesized compounds was tested in vitro against various cancer cell lines, such as MCF‐7, MDA‐MB‐231 (human breast), HT‐29, HCT 116 (colon cancer), A549 (human lung carcinoma), and Vero cells. Among the screened compounds, 3e, 3h, and 3i demonstrated potent anticancer activity, with compound 3h surpassing the reference drug cisplatin against A549, MCF7, MDA‐MB‐231, and HCT116 cancer cells. The introduction of an electron‐withdrawing group on the phenyl ring resulted in increased anticancer activity. The most potent compounds, 3e, 3h, and 3i, were tested against VEGFR‐2, HER2, and EGFR in multikinase inhibition assays, with compounds 3h and 3i showing improved potency against the HER2 kinase. The compounds formed two H‐bonds with amino acids, indicating that they had a high affinity for the target HER2 kinase (PDB ID: 3RCD), according to the docking analysis. The absorption, distribution, metabolism, excretion, and toxicity properties of the optimized analogs were also assessed in vitro, enabling the discovery of promising anticancer agents. Finally, the B3LYP level was used to measure density functional theory geometry optimization and the related quantum parameters for the active compounds.

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Section: Introductionmentioning

confidence: 99%

Microwave‐assisted N‐alkylation of amines with alcohols catalyzed by MnCl₂: Anticancer, docking, and DFT studies

Kumar

Kumar²,

Prasad³

et al. 2022

Archiv der Pharmazie

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“…In continuation of our effort on the synthesis of nitrogen containing heterocycles, − herein, we report one-pot synthesis of precursor required for the synthesis of imidazole derivatives using 4-(trifluoromethyl)benzene diazonium salt and 4-nitrostyrene in the presence of catalytic amount of PtO 2 and OsO 4 (Figure , Scheme A). Subsequently, we described a MoS 2 –CA4 catalyzed synthesis of 2,4,5-trisubstituted imidazoles from 1-(4-nitro phenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione, aldehydes and ammonium acetate under solvent-free conditions using a reusable heterogeneous catalyst (Figure , Scheme B).…”

Section: Introductionmentioning

confidence: 99%

MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

Raghu¹,

Kumar²,

Prasad³

et al. 2020

ACS Comb. Sci.

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A MoS2-supported-calix[4]arene (MoS2-CA4) nanocatalyst was used for efficient synthesis of 2,4,5-trisubstituted imidazole derivatives from 1-(4-nitrophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione, aldehydes and ammonium acetate under solvent-free conditions. Reusability of the catalyst up to five cycles without any significant loss in the yields of the product is the unique feature of this heterogeneous solid catalysis. Furthermore, the noteworthy highlights of this method are safe reaction profiles, broad substrate scope, excellent yields, economical, solvent-free, and simple workup conditions. All synthesized compounds were evaluated for their in vitro antitubercular (TB) activity against Mycobacterium tuberculosis (Mtb) H37Rv. Among the screened compounds 3c, 3d, 3f, 3m, and 3r had MIC values of 2.15, 2.78, 5.75, 1.36, and 0.75 μM, respectively, and exhibited more potency than the reference drugs pyrazinamide (MIC: 3.12 μM), ciprofloxacin (MIC: 4.73 μM), and ethambutol (7.61 μM). Besides, potent compounds (3c, 3d, 3f, 3m, and 3r) have been tested for inhibition of MabA (β-ketoacyl-ACP reductase) enzyme and cytotoxic activity against mammalian Vero cell line. A molecular docking study was carried out on the MabA (PDB ID: 1UZN) enzyme to predict the interactions of the synthesized compounds. The results of the in vitro anti-TB activity and docking study showed that synthesized compounds have a strong anti-TB activity and can be adapted and produced more effectively as a lead compound.

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Discovery of a novel series of substituted quinolines acting as anticancer agents and selective EGFR blocker: Molecular docking study

Kumar¹,

Raghu²,

Prathibha³

et al. 2021

Bioorganic & Medicinal Chemistry Letters

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Efficient Synthesis of RuO₂ Nanoparticle with excellent activity for one‐pot Synthesis of 2,3‐disubstituted quinazolin‐4(1H)‐ones

Cited by 12 publications

References 24 publications

Microwave‐assisted N‐alkylation of amines with alcohols catalyzed by MnCl₂: Anticancer, docking, and DFT studies

Microwave‐assisted N‐alkylation of amines with alcohols catalyzed by MnCl₂: Anticancer, docking, and DFT studies

MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

Discovery of a novel series of substituted quinolines acting as anticancer agents and selective EGFR blocker: Molecular docking study

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Efficient Synthesis of RuO2 Nanoparticle with excellent activity for one‐pot Synthesis of 2,3‐disubstituted quinazolin‐4(1H)‐ones

Cited by 12 publications

References 24 publications

Microwave‐assisted N‐alkylation of amines with alcohols catalyzed by MnCl2: Anticancer, docking, and DFT studies

Microwave‐assisted N‐alkylation of amines with alcohols catalyzed by MnCl2: Anticancer, docking, and DFT studies

MoS2–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis

Discovery of a novel series of substituted quinolines acting as anticancer agents and selective EGFR blocker: Molecular docking study

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Efficient Synthesis of RuO₂ Nanoparticle with excellent activity for one‐pot Synthesis of 2,3‐disubstituted quinazolin‐4(1H)‐ones

Microwave‐assisted N‐alkylation of amines with alcohols catalyzed by MnCl₂: Anticancer, docking, and DFT studies

Microwave‐assisted N‐alkylation of amines with alcohols catalyzed by MnCl₂: Anticancer, docking, and DFT studies

MoS₂–Calix[4]arene Catalyzed Synthesis and Molecular Docking Study of 2,4,5-Trisubstituted Imidazoles As Potent Inhibitors of Mycobacterium tuberculosis