Facile one-pot three-component synthesis of 4,6-diaryl-3,4-dihydropyrimidine-2(1<i>H</i>)-thiones under ultrasonic irradiation

Abbass, Shymaa A.; Moustafa, Gamal A. I.; Hassan, Heba A.; Abuo‐Rahma, Gamal El‐Din A.

doi:10.1080/00397911.2019.1652759

Cited by 4 publications

(3 citation statements)

References 21 publications

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“…4,6-Diphenyl-3,4-dihydropyrimidine-2(1H)-thione, KKII5. 60 To a stirred solution of NaOH (68 mg, 1.70 mmol) in EtOH (3.5 mL) were added E-chalcone (0.35 g, 1.70 mmol) and thiourea (0.13 g, 1.70 mmol), and the mixture was sonicated for 1 h at room temperature. Then it was poured in ice−water, and the solid formed was filtered, washed with H 2 O, EtOH/ H 2 O 1:1, and dried to give KKII5 as an off-yellow solid in 97% yield.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Thiocarbohydrazone and Chalcone-Derived 3,4-Dihydropyrimidinethione as Lipid Peroxidation and Soybean Lipoxygenase Inhibitors

et al. 2023

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The potential of the 4,6-diphenyl-3,4-dihydropyrimidine-2(1H)-thione (abbreviated as KKII5) and (E)-N′-benzylidenehydrazinecarbothiohydrazide (abbreviated as DKI5) compounds as possible drug leads is investigated. KKII5 and DKI5 are synthesized in high yield of up to 97%. Their structure, binding in the active site of the LOX-1 enzyme, and their toxicity are studied via joint experimental and computational methodologies. Specifically, the structure assignment and conformational analysis were achieved by applying homonuclear and heteronuclear 2D nuclear magnetic resonance (NMR) spectroscopy (2D-COSY, 2D-NOESY, 2D-HSQC, and 2D-HMBC) and density functional theory (DFT). The obtained DFT lowest energy conformers were in agreement with the NOE correlations observed in the 2D-NOESY spectra. Additionally, docking and molecular dynamics simulations were performed to discover their ability to bind and remain stabile in the active site of the LOX-1 enzyme. These in silico experiments and DFT calculations indicated favorable binding for the enzyme under study. The strongest binding energy, −9.60 kcal/mol, was observed for dihydropyrimidinethione KKII5 in the active site of LOX-1. ADMET calculations showed that the two molecules lack major toxicities and could serve as possible drug leads. The redox potential of the active center of LOX-1 with the binding molecules was calculated via DFT methodology. The results showed a significantly smaller energy attachment of 2.8 eV with KKII5 binding in comparison to DKI5. Thus, KKII5 enhanced the ability of the active center to receive electrons compared to DKI5. This is related to the stronger binding interaction of KKII5 relative to that of DK15 to LOX-1. The two very potent LOX-1 inhibitors exerted IC50 19 μΜ (KKII5) and 22.5 μΜ (DKI5). Furthermore, they both strongly inhibit lipid peroxidation, namely, 98% for KKII5 and 94% for DKI5.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Thiocarbohydrazone and Chalcone-Derived 3,4-Dihydropyrimidinethione as Lipid Peroxidation and Soybean Lipoxygenase Inhibitors

et al. 2023

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“…Another pyrimidine series were synthesized from acetophenone and aromatic aldehyde derivatives (9) in the presence of thiourea in ethanol and KOH at 50 C in ultrasonic bath for 30-90 min has produced the desired pyrimidine (11) in 78%-95% yield. In this one-pot method, the chalcone intermediate was formed and directly converted to pyrimidine 11 [170] (Scheme 3). The ultrasound technique is commonly used in research as an ecofriendly, green method that formed products in minutes as compared to the conventional method, which completes the reaction with long reflux at high temperature.…”

Section: One-pot Methodsmentioning

confidence: 99%

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Farooq

Ngaini

2021

Journal of Heterocyclic Chem

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Chalcone-derived pyrimidine is a well-known heterocyclic compound that is commonly present in ribonucleic acid (RNA) and deoxyribonucleic acid (DNA) bio-isosteres. Pyrimidine derivatives are effective in both the electronic industry and drug industries. This review highlights the synthesis of pyrimidines, namely mono-pyrimidine, bis-pyrimidine, fused pyrimidine, symmetric, and asymmetric pyrimidine via one-pot and two-pot methods. The one-pot method is the direct reaction of amino derivatives with aldehydes and acetophenones, whereas the two-pot method is frequently reported for the synthesis of chalcone before the cyclization to a pyrimidine. This review is important in organic synthesis, particularly in the heterocyclic field, regarding pyrimidines and their significance in therapeutic and electronic industries.

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“…1 (39). 62 Following the general method F using chalcone (11), compound 39 was obtained as a beige solid in 45% yield. R f = 0.56 (PE/AcOEt 8:2).…”

Section: 1 5 N ′ -( ( 1 E 2 E ) -3 -( -C H L O R O P H E N Y L ) ...mentioning

confidence: 99%

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

Tabor,

Katsogiannou,

Karta

et al. 2023

ACS Omega

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A series of 32 thiourea-based urease inhibitors were synthesized and evaluated against native bacterial enzyme and whole cells of Sporosarcina pasteurii and Proteus mirabilis strains. The proposed inhibitors represented structurally diverse thiosemicarbazones and thiocarbohydrazones, benzyl-substituted thiazolyl thioureas, 1H-pyrazole-1-carbothioamides, and dihydropirimidine-2(1H)-thiones. Kinetic characteristics with purified S. pasteurii enzyme determined low micromolar inhibitors within each structural group. (E)-2-(1-Phenylethylidene)hydrazine-1-carbothioamide 19 (K i = 0.39 ± 0.01 μM), (E)-2-(4-methylbenzylidene)hydrazine-1-carbothioamide 16 (K i = 0.99 ± 0.04 μM), and N′-((1E,2E)-1,3-diphenylallylidene)hydrazinecarbothiohydrazide 29 (K i = 2.23 ± 0.19 μM) were used in modeling studies that revealed sulfur ion coordination of the active site nickel ion and hydrogen bonds between the amide group and the side chain of Asp363 and Ala366 carbonyl moiety. Whole-cell studies proved the activity of compounds in Gram-positive and Gram-negative microorganisms. Ureolysis control observed in P. mirabilis PCM 543 (e.g., IC 50 = 304 ± 14 μM for 1-benzyl-3-(4-(4-hydroxyphenyl)thiazol-2-yl)thiourea 52) is a valuable achievement, as urease is recognized as a major virulence factor of this urinary tract pathogen.

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Facile one-pot three-component synthesis of 4,6-diaryl-3,4-dihydropyrimidine-2(1H)-thiones under ultrasonic irradiation

Cited by 4 publications

References 21 publications

Thiocarbohydrazone and Chalcone-Derived 3,4-Dihydropyrimidinethione as Lipid Peroxidation and Soybean Lipoxygenase Inhibitors

Thiocarbohydrazone and Chalcone-Derived 3,4-Dihydropyrimidinethione as Lipid Peroxidation and Soybean Lipoxygenase Inhibitors

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

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