Synthesis, antitumor activity and molecular docking study of some novel 3-benzyl-4(3H)quinazolinone analogues

Al-Suwaidan, Ibrahim A.; Abdel‐Aziz, Alaa A.‐M.; Shawer, Taghreed Z.; Ayyad, Rezk R.; Alanazi, Amer M.; El_Morsy, Ahmad M.; Mohamed, Menshawy A.; Abdel-Aziz, Naglaa I.; El‐Sayed, Magda A.‐A.; El‐Azab, Adel S.

doi:10.3109/14756366.2015.1004059

Cited by 66 publications

(48 citation statements)

References 12 publications

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“…Geometric optimization for 3-D compounds was performed using Hyperchem release 8.0.7. hypercube Inc. The methodology used for docking was in accordance with the literature [49,50].…”

Section: Molecular Docking Methodologymentioning

confidence: 99%

Ultrasound one pot synthesis of fused quinazolinones and quinazolinediones, screening and molecular docking study as phosphodiesterase 7A inhibitors.

et al. 2019

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P HOSPHODIESTERASE 7A enzyme is one of the most recent targets for designing potent anti-inflammatory agents with minimal side effects. Quinazolinones are unique building blocks of wide biological activities. Different quinazolinones were reported to act as Phosphodiesterase 7A inhibitors anti-inflammatory particularly against chronic inflammation and autoimmune disease. Ultrasound is a green convenient method for synthesis of different heterocyclic ring system that is advantageous in terms of yield and reaction time. Ultrasound was used for one pot synthesis of 3-substituted 6-aryldihydroisoindolo[2,1-a] quinazolin-5,11diones and 3-arylquinazolin-2,4(1H,3H)-diones. Seventeen compounds were synthesized in good yields. The synthesized compounds were inspected for in vitro inhibitory activity against phosphodiesterase7A enzyme. Molecular docking was used to study the mode of interaction of all the synthesized compounds into the enzyme phosphodiesterase 7A binding site. Five compounds showed high inhibitory activity of enzyme Phosphodiesterase 7A at micro-molar level compared to reference drug. The compounds showed good recognition at the enzyme binding site in the molecular docking. There was a good agreement between the molecular docking and the biological screening results.

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“…Geometric optimization for 3-D compounds was performed using Hyperchem release 8.0.7. hypercube Inc. The methodology used for docking was in accordance with the literature [49,50].…”

Section: Molecular Docking Methodologymentioning

confidence: 99%

Ultrasound one pot synthesis of fused quinazolinones and quinazolinediones, screening and molecular docking study as phosphodiesterase 7A inhibitors.

et al. 2019

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“…In our laboratory, research efforts have concentrated on synthesizing quinazoline derivatives with substituted moieties having high lipophilic properties in the hope of developing effective and safe compounds [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Herein, we report the crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one as a methaqualone analogue.…”

Section: Commentmentioning

confidence: 99%

Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C₁₇H₁₅IN₂O

El‐Azab

Ghabbour

Abdel‐Aziz

et al. 2019

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Quinazolinones were considered to be a scaffold with potential biological activities. Besides possessing a variety of biological effects including antimicrobial [1][2][3][4][5][6], anticonvulsant [7,8], and antihistamine [9,10] activities, compounds containing quinazolin-4-one nucleus also showed promising anticancer potency [11][12][13][14][15][16][17][18][19][20]. Along with that, 5-arylidene-2thioxothiazolidine-4-one compounds are an important class of compounds with a wide range of pharmaceutical properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of SomeN-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds

Nguyen

Dao

et al. 2019

Journal of Chemistry

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Ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (3) which was synthesized starting from anthranilic acid (1) via 2-thioxo-3-phenylquinazolin-4(3H)-one (2) reacted with hydrazine hydrate to afford 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetohydrazide (4). Reaction of (4) with thiocarbonyl-bis-thioglycolic acid gave a new compound name N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide (5). Knoevenagel condensation of (5) with appropriate aldehydes gave fourteen (Z)-N-(5-arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide compounds (6a–o) with moderate yield. The chemical structure of the compounds was elucidated on the basis of IR, 1H-NMR, 13C-NMR, and HR-MS spectral data. The 5-arylidene-2-thioxothiazolidinone compounds exhibited mild-to-moderate cytotoxic activity against both K562 (chronic myelogenous leukemia) cells and MCF7 (breast cancer) cells.

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Synthesis, antitumor activity and molecular docking study of some novel 3-benzyl-4(3H)quinazolinone analogues

Cited by 66 publications

References 12 publications

Ultrasound one pot synthesis of fused quinazolinones and quinazolinediones, screening and molecular docking study as phosphodiesterase 7A inhibitors.

Ultrasound one pot synthesis of fused quinazolinones and quinazolinediones, screening and molecular docking study as phosphodiesterase 7A inhibitors.

Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C₁₇H₁₅IN₂O

Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of SomeN-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds

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Synthesis, antitumor activity and molecular docking study of some novel 3-benzyl-4(3H)quinazolinone analogues

Cited by 66 publications

References 12 publications

Ultrasound one pot synthesis of fused quinazolinones and quinazolinediones, screening and molecular docking study as phosphodiesterase 7A inhibitors.

Ultrasound one pot synthesis of fused quinazolinones and quinazolinediones, screening and molecular docking study as phosphodiesterase 7A inhibitors.

Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O

Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of SomeN-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds

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Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C₁₇H₁₅IN₂O