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Keywords = 6-aryl-2-styrylquinazolin-4(3H)-ones

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14 pages, 1701 KiB  
Article
Citric Acid-Catalyzed Three-Component Synthesis of (E)-3-Aryl-2-styryl-2,3-dihydroquinazoline-4(1H)-ones and Their Mild Oxidation with I2/DMSO System into (E)-3-Aryl-2-styrylquinazolin-4(3H)-ones
by Vladimir V. Kouznetsov, Angélica Peñaranda Gómez and Carlos E. Puerto Galvis
Chemistry 2025, 7(2), 42; https://doi.org/10.3390/chemistry7020042 - 16 Mar 2025
Viewed by 873
Abstract
We hereby report a simple and efficient method for the preparation of (E)-3-aryl-2-styryl-2,3-dihydroquinazolin-4-(1H)-ones, from isatoic anhydride, anilines, and cinnamaldehydes in the presence of 20 mol% citric acid in methanol at 60 °C for 2 h. The styryl-dihydroquinazolin-4-(1H)-one [...] Read more.
We hereby report a simple and efficient method for the preparation of (E)-3-aryl-2-styryl-2,3-dihydroquinazolin-4-(1H)-ones, from isatoic anhydride, anilines, and cinnamaldehydes in the presence of 20 mol% citric acid in methanol at 60 °C for 2 h. The styryl-dihydroquinazolin-4-(1H)-one products were obtained in moderate and good yields (30–80%) through the three-component condensation reaction, under an environment-friendly protocol. The latter were easily transformed into styrylquinazolin-4-(3H)-one derivatives with 57–91% yields using a mild oxidation with an I2/DMSO system for less than 60 min. Full article
(This article belongs to the Section Molecular Organics)
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15 pages, 2340 KiB  
Article
Synthesis, Biological Evaluation and Molecular Docking Studies of 6-Aryl-2-Styrylquinazolin-4(3H)-Ones
by Emmanuel Ndubuisi Agbo, Tshepiso Jan Makhafola, Yee Siew Choong, Malose Jack Mphahlele and Ponnadurai Ramasami
Molecules 2016, 21(1), 28; https://doi.org/10.3390/molecules21010028 - 25 Dec 2015
Cited by 11 | Viewed by 5868
Abstract
Suzuki-Miyaura cross-coupling of 6-bromo-2-styrylquinazolin-4(3H)-ones with arylboronic acids afforded a series of novel 6-aryl-2-styrylquinazolin-4(3H)-ones. These compounds were evaluated for potential anticancer properties against the human renal (TK-10), melanoma (UACC-62) and breast cancer (MCF-7) cell lines. Their antimicrobial properties were also [...] Read more.
Suzuki-Miyaura cross-coupling of 6-bromo-2-styrylquinazolin-4(3H)-ones with arylboronic acids afforded a series of novel 6-aryl-2-styrylquinazolin-4(3H)-ones. These compounds were evaluated for potential anticancer properties against the human renal (TK-10), melanoma (UACC-62) and breast cancer (MCF-7) cell lines. Their antimicrobial properties were also evaluated against six Gram-positive and four Gram-negative bacteria, as well as two strains of fungi. Molecular docking studies (in silico) were conducted on compounds 5a, b, d and 6a, b, df to recognize the hypothetical binding motif of the title compounds within the active site of the dihydrofolate reductase and thymidylate synthase enzymes. Full article
(This article belongs to the Section Bioorganic Chemistry)
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