Synthesis and Biological Activity Studies of Novel Pyrido[2,3-d]pyrimidines and Pyrido[2,3-d]triazines

Elsaedany, Samir Kamel; Zein, Mohamed A.-E.; Abdelrehim, El-sayed M.; Keshk, Reda Mohammed

doi:10.1134/s1068162021020114

Cited by 11 publications

(3 citation statements)

References 22 publications

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“…A literature survey revealed that pyrido [2,3- d ] pyrimidine derivatives have important potential in pharmaceutical and medicinal chemistry due to their diverse range of biological activity, including anti-viral properties [ 1 ], antioxidant [ [2] , [3] , [4] , [5] ], antimicrobial [ [6] , [7] , [8] ], anti-inflammatory [ [9] , [10] , [11] ], antitubercular [ 12 ], it is also used as an inhibitor of some enzymes such as dihydrofolate reductase inhibition [ 13 , 14 ], glucosidase inhibition [ 15 , 16 ], a threonine tyrosine kinase (TTK) inhibition [ 17 ] and adenosine kinase inhibition [ 18 ]. The pyrimidine moiety has excellent chemical, physical and biological properties, especially when it is combined with heterocyclic compounds, for example: Thieno [2,3-d] pyrimidine is a compound that possesses antioxidant, anticancer, and antitumor properties [ [19] , [20] , [21] , [22] , [23] ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, anticancer activity and molecular docking of new quinolines, quinazolines and 1,2,4-triazoles with pyrido[2,3-d] pyrimidines

Abu-Hashem,

Hakami,

Amri

2024

Heliyon

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Section: Introductionmentioning

confidence: 99%

Synthesis, anticancer activity and molecular docking of new quinolines, quinazolines and 1,2,4-triazoles with pyrido[2,3-d] pyrimidines

Abu-Hashem,

Hakami,

Amri

2024

Heliyon

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“…Pyrido [2,3-d]pyrimidine is a privileged heterocyclic scaffold in drug design. Pyrido [2,3-d]pyrimidine ring systems have several biological and pharmacological activities, such as being analgesic, anti-inflammatory [14][15][16][17], anticancer [18], antitubercular [19], antimicrobial [20][21][22], a threonine tyrosine kinase (TT) inhibitor [23], an adenosine kinase inhibitor [24], a dihydrofolate reductase inhibitor [25,26], antiviral [27] and antioxidant [28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Novel Pyrimidine Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Molecular Modeling Studies

Myriagkou,

Papakonstantinou,

Deligiannidou

et al. 2023

Molecules

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The heterocyclic ring system of pyrido [2,3-d]pyrimidines is a privileged scaffold in medicinal chemistry, possessing several biological activities. The synthesis of the pyrimidine derivatives was performed via the condensation of a suitable α,β-unsaturated ketone with 4-amino-6-hydroxy-2-mercaptopyrimidine monohydrate in glacial acetic acid. Chalcones were synthesized, as starting materials, via the Claisen–Schmidt condensation of an appropriately substituted ketone and an appropriately substituted aldehyde in the presence of aqueous KOH 40% w/v in ethanol. All the synthesized compounds were characterized using IR, 1H-NMR, 13C-NMR, LC-MS and elemental analysis. The synthesized compounds were evaluated for their antioxidant (DPPH assay), anti-lipid peroxidation (AAPH), anti-LOX activities and ability to interact with glutathione. The compounds do not interact significantly with DPPH but strongly inhibit lipid peroxidation. Pyrimidine derivatives 2a (IC50 = 42 μΜ), 2f (IC50 = 47.5 μΜ) and chalcone 1g (IC50 = 17 μM) were the most potent lipoxygenase inhibitors. All the tested compounds were found to interact with glutathione, apart from 1h. Cell viability and cytotoxicity assays were performed with the HaCaT and A549 cell lines, respectively. In the MTT assay towards the HaCaT cell line, none of the compounds presented viability at 100 μM. On the contrary, in the MTT assay towards the A549 cell line, the tested compounds showed strong cytotoxicity at 100 μM, with derivative 2d presenting the strongest cytotoxic effects at the concentration of 50 μΜ.

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“…Pyrido [2,3-d]pyrimidine is one of the most privileged heterocyclic frameworks in several efficacious pharmacological compounds. Pyrido [2,3-d]pyrimidine ring systems have assorted biological and pharmacological activities such as being analgesic, anti-inflammatory [1-3], antitubercular [4], antimicrobial [5][6][7], a threonine tyrosine kinase (TTK) inhibitor [8], an adenosine kinase inhibitor [9], antiviral [10], antioxidant [11][12][13][14], a dihydrofolate reductase inhibitor [15,16], and an efficient glucosidase inhibitor [17,18]. Moreover, the 1,3-benzothiazole nucleus is a highly significant scaffold in the drug design, due to important pharmacological and medicinal activities, such as being antiviral [19], antituberculosis [20], an identifier of selective CB2 receptor ligands [21], antitumor [22][23][24], antimicrobial [25][26][27], anticonvulsant [28], a schistosome BCL-2 inhibitor [29], antidiabetic [30], antioxidant [31], an anti-Alzheimer drug [32] and a urease inhibitor [33] among the heterocyclic compounds containing a pyrimidine and benzothiazole nucleus that exhibits biological activity [34][35][36] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis

et al. 2022

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In our attempt towards the synthesis and development of effective antimicrobial, anticancer and antioxidant agents, a novel series of 2,3-dihydropyrido[2,3-d]pyrimidin-4-one 7a–e and pyrrolo[2,1-b][1,3]benzothiazoles 9a–e were synthesized. The synthesis of 2-(1,3-benzo thiazol-2-yl)-3-(aryl)prop-2-enenitrile (5a–e) as the key intermediate was accomplished by a microwave efficient method. Via a new variety oriented synthetic microwave pathway, these highly functionalized building blocks allowed access to numerous fused heteroaromatic such as 7-amino-6-(1,3-benzo thiazol-2-yl)-5-(aryl)-2-thioxo-2,3dihydropyrido [2,3-d]pyrimidin-4(1H)-one 7a–e and 1-amino-2-(aryl)pyrrolo[2,1-b][1,3]benzothiazole-3-carbonitrile derivatives 9a–e in order to study their antimicrobial and anticancer activity. The present investigation offers effective and rapid new procedures for the synthesis of the newly polycondensed heterocyclic ring systems. All the newly synthesized compounds were evaluated for antimicrobial, anticancer and antioxidant activity. Compounds 7a,d, and 9a,d showed higher antimicrobial activity than cefotaxime and fluconazole while the remaining compounds exhibited good to moderate activity against bacteria and fungi. An anticancer evaluation of the newly synthesized compounds against the three tumor cell lines (lung cell NCI-H460, liver cancer HepG2 and colon cancer HCT-116) exhibited that compounds 7a, d, and 9a,d have higher cytotoxicity against the three human cell lines compared to doxorubicin as a reference drug. These compounds also exhibited higher antioxidant activity and a great ability to protect DNA from damage induced by bleomycin.

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Synthesis and Biological Activity Studies of Novel Pyrido[2,3-d]pyrimidines and Pyrido[2,3-d]triazines

Cited by 11 publications

References 22 publications

Synthesis, anticancer activity and molecular docking of new quinolines, quinazolines and 1,2,4-triazoles with pyrido[2,3-d] pyrimidines

Synthesis, anticancer activity and molecular docking of new quinolines, quinazolines and 1,2,4-triazoles with pyrido[2,3-d] pyrimidines

Novel Pyrimidine Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Molecular Modeling Studies

Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis

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