ChemInform Abstract: Synthesis of Novel 4,6‐Disubstituted Quinazoline Derivatives, Their Antiinflammatory and Anticancer Activity (Cytotoxic) Against U937 Leukemia Cell Lines.

Chandrika, P. Mani; Yakaiah, T.; Rao, A. Raghu Ram; Narsaiah, B.; Reddy, N. Chakra; Sridhar, V.; Rao, J. Venkateshwara

doi:10.1002/chin.200835147

Cited by 4 publications

(4 citation statements)

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“…The synthetic quinazoline ring is part of several antibiotics that are known to inhibit the growth of Gram‐positive bacteria and that are also active against various transplantable tumors . Many of them show analgesic, antifungal, antibacterial, anticancer, and anti‐inflammatory activities . As pesticides, they are used as insecticidal and antiviral agents .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Characterization, and Time‐Dependent DFT Calculations of 1‐Methyl‐5‐phenyl‐5H‐pyrido[1,2‐a]quinazoline‐3,6‐dione and Its Starting Precursor in Different Solvents

Hamada

2018

ChemistryOpen

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In this study, 2‐mercapto‐3‐phenyl‐2,3‐dihydro‐1H‐quinazolin‐4‐one (1), which exists as a thiol and thione tautomer, was treated with acetylacetone to give the target compound, namely, 1‐methyl‐5‐phenyl‐5H‐pyrido[1,2‐a]quinazoline‐3,6‐dione (2). The spectroscopic data, including UV/Vis, IR, 1H NMR, 13C NMR, and mass data, of this compound were recorded. The molecular structures of the starting material (1) and the product (2) were optimized by using density functional theory (DFT) by employing the B3LYP exchange correlation with the 6‐311G (d, p) and 6‐31G++ (d, p) basis sets. The electronic spectra were determined based on time‐dependent DFT calculations in three different solvents (i.e., chloroform, ethanol, and acetonitrile) starting from the same solvated run of the optimized geometry with the same two basis sets. The solvent effects were considered based on the polarizable continuum model (PCM), and the energetic behavior of the compounds and the total static dipole moment (μ) in different solvents were examined in the two basis sets; the results showed that the total energy of the compounds decreased upon increasing the polarity of the solvent. Time‐dependent DFT calculations were performed to analyze the electronic transitions for various excited states that reproduced the experimental band observed in the UV/Vis spectrum. A study on the electronic properties, such as the HOMO and LUMO energies, was performed by the time‐independent DFT approach. Using the gauge‐independent atomic orbital method (GIAO), the 1H NMR chemical shifts were calculated and correlated with the experimental ones. The computed results showed that the introduction of different dielectric media had a slight effect on the stability and reactivity of the title compound as well as on the Milliken atomic charges and the molecular geometry. Besides, the molecular electrostatic potential of target product 2 was evaluated in different solvents.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Characterization, and Time‐Dependent DFT Calculations of 1‐Methyl‐5‐phenyl‐5H‐pyrido[1,2‐a]quinazoline‐3,6‐dione and Its Starting Precursor in Different Solvents

Hamada

2018

ChemistryOpen

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“…As a result of their diverse pharmacological activities such as anticancer [12,13], antimicrobial [14e16], antimalarial [17,18], anti-inflammatory [19e22], antihypertensive [23,24], anticonvulsant [25,26] and cholinesterase inhibition activities [27], these derivatives have received considerable attention. However, a lack of studies is clearly noticed that are to utilize the property that quinazolinone derivatives could arrest mutant p53 while maintaining steady-state protein levels.…”

Section: Introductionmentioning

confidence: 99%

Distinct novel quinazolinone exhibits selective inhibition in MGC-803 cancer cells by dictating mutant p53 function

Zhang

Xue

et al. 2015

European Journal of Medicinal Chemistry

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“…Quinazolinones are versatile nitrogen containing heterocyclic compounds, possessing a broad spectrum of biological and pharmacological activities such as hypotensive [1], anticancer [2], anti-HIV [3], anti-inflammatory [4], analgesic [5], antiviral [6], antitubercular [7], antimicrobial [8], antibacterial [9,10] etc. Tetrazoles [11,12] are medicinally important heterocycles incorporated in a large number of drugs.…”

Section: Introductionmentioning

confidence: 99%

2-Methyl-3-{4-[2-(1H-tetrazol-5-yl)ethylamino]phenyl}-3H-quinazolin-4-one

Arulmurugan¹,

Kavitha²

2010

Molbank

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This present work aims at synthesizing a novel tetrazole from quinazolinone. 3-(4-Aminophenyl)-2-methyl-3H-quinazolin-4-one is converted into a nitrile by reacting it with acrylonitrile and triton B. The nitrile on treatment with NaN3, NH4Cl and DMF yielded the corresponding tetrazole. The tetrazole obtained was characterized by IR, 1H NMR, EI-MS and elemental analysis. The compound was screened for antimicrobial activity against Staphylococcus aureus, Escherichia coli, Candida albicans and Aspergillus niger.The results of the study show that the compound possesses fairly good antimicrobial activity against the test organisms

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ChemInform Abstract: Synthesis of Novel 4,6‐Disubstituted Quinazoline Derivatives, Their Antiinflammatory and Anticancer Activity (Cytotoxic) Against U937 Leukemia Cell Lines.

Cited by 4 publications

References 1 publication

Synthesis, Spectroscopic Characterization, and Time‐Dependent DFT Calculations of 1‐Methyl‐5‐phenyl‐5H‐pyrido[1,2‐a]quinazoline‐3,6‐dione and Its Starting Precursor in Different Solvents

Synthesis, Spectroscopic Characterization, and Time‐Dependent DFT Calculations of 1‐Methyl‐5‐phenyl‐5H‐pyrido[1,2‐a]quinazoline‐3,6‐dione and Its Starting Precursor in Different Solvents

Distinct novel quinazolinone exhibits selective inhibition in MGC-803 cancer cells by dictating mutant p53 function

2-Methyl-3-{4-[2-(1H-tetrazol-5-yl)ethylamino]phenyl}-3H-quinazolin-4-one

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