Synthesis, Cytotoxic Activity and Molecular Modelling of Novel [1,2,3]triazolo[4,5-d]pyrimidine Compounds, their Glycoside Derivatives and Acyclic Analogs | ||||
Egyptian Journal of Chemistry | ||||
Article 62, Volume 65, Issue 1, January 2022, Page 645-656 PDF (728.25 K) | ||||
Document Type: Original Article | ||||
DOI: 10.21608/ejchem.2021.84371.4127 | ||||
View on SCiNiTO | ||||
Authors | ||||
Ashraf M Mohamed 1; Mohamed Abdelwahab2; dina elnaggar 3; Naglaa Abdelsamei Abde lHafez4; Salwa Faheem Mahmoud5; Mohamed El-Bayaa6; Dina S. El-kady 7; Mervat Mostafa Omran 8; Wael A. El-Sayed9 | ||||
1Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo, Egypt. | ||||
2Applied organic chemistry, National Research Center | ||||
3Department of Applied Organic Chemistry, Industrial Chemical Division, National Research Center, Cairo, Dokki 12622, Egypt | ||||
4Applied Organic Chem, NRC | ||||
5Applied Organic Chemistry Department, National Research Center, Cairo, Dokki, 12622, Egypt | ||||
6Photochemistry Department, National Research Centre | ||||
7hormones department, medical research division, National research center | ||||
8Department of Cancer Biology, Pharmacology Unit, National Cancer Institute, Cairo University, Cairo 11796, Egypt | ||||
9Photochemistry Department, Naional Research Centre, Dokki, Cairo, Egypt | ||||
Abstract | ||||
Novel substituted [1,2,3]triazolo[4,5-d]pyrimidine-7-one derivatives were synthesized using 1,2,3-triazolo-4-carboxamide derivative (2) by the reaction with carbon disulfide, triethoxymethane, 4-fluorobenzaldehyde and ethyl benzoate respectively. The S-glucoside, N-glycoside derivatives and acyclic sugar analogs of new synthesized [1,2,3]triazolo[4,5-d]pyrimidines were also synthesized. The synthesized compounds were tested for cytotoxicity and in vitro anticancer activity versus human lung (A549), colon (HCT116) and breast (MCF-7) cancer cell lines. The results disclosed that the synthesized compounds apply their activities in A549 and MCF-7. MCF-7 cells are more sensitive to the tested compounds than the other cell lines. Compounds 2, 3, 9 and 10 exposed promising anticancer activities compared to the action of the ordinarily used anticancer drug, doxorubicin in both A549 and MCF-7 cell lines. A good binding affinities for compounds 2, 3, 6, 10 and 11 were noted in docking studies. Results showed a clear effect of N3-substitution in pyrimidine ring on the activities of the synthesized compounds | ||||
Keywords | ||||
Triazolo[4,5-d]pyrimidine, Glycosides, Anticancer; A549, HCT116, MCF-7 | ||||
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