Synthesis, Cytotoxic Activity and Molecular Modelling of Novel [1,2,3]triazolo[4,5-d]pyrimidine Compounds, their Glycoside Derivatives and Acyclic Analogs
Mohamed, A., Abdelwahab, M., elnaggar, D., Abde lHafez, N., Mahmoud, S., El-Bayaa, M., El-kady, D., Omran, M., El-Sayed, W. (2022). Synthesis, Cytotoxic Activity and Molecular Modelling of Novel [1,2,3]triazolo[4,5-d]pyrimidine Compounds, their Glycoside Derivatives and Acyclic Analogs. EKB Journal Management System, 65(1), 645-656. doi: 10.21608/ejchem.2021.84371.4127
Ashraf M Mohamed; Mohamed Abdelwahab; dina elnaggar; Naglaa Abdelsamei Abde lHafez; Salwa Faheem Mahmoud; Mohamed El-Bayaa; Dina S. El-kady; Mervat Mostafa Omran; Wael A. El-Sayed. "Synthesis, Cytotoxic Activity and Molecular Modelling of Novel [1,2,3]triazolo[4,5-d]pyrimidine Compounds, their Glycoside Derivatives and Acyclic Analogs". EKB Journal Management System, 65, 1, 2022, 645-656. doi: 10.21608/ejchem.2021.84371.4127
Mohamed, A., Abdelwahab, M., elnaggar, D., Abde lHafez, N., Mahmoud, S., El-Bayaa, M., El-kady, D., Omran, M., El-Sayed, W. (2022). 'Synthesis, Cytotoxic Activity and Molecular Modelling of Novel [1,2,3]triazolo[4,5-d]pyrimidine Compounds, their Glycoside Derivatives and Acyclic Analogs', EKB Journal Management System, 65(1), pp. 645-656. doi: 10.21608/ejchem.2021.84371.4127
Mohamed, A., Abdelwahab, M., elnaggar, D., Abde lHafez, N., Mahmoud, S., El-Bayaa, M., El-kady, D., Omran, M., El-Sayed, W. Synthesis, Cytotoxic Activity and Molecular Modelling of Novel [1,2,3]triazolo[4,5-d]pyrimidine Compounds, their Glycoside Derivatives and Acyclic Analogs. EKB Journal Management System, 2022; 65(1): 645-656. doi: 10.21608/ejchem.2021.84371.4127

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, Pages 645-656    PDF (728.25 K)
Document Type: Original Article
DOI: 10.21608/ejchem.2021.84371.4127
Authors
Ashraf M Mohamed* 1; Mohamed Abdelwahab2; dina elnaggar3; Naglaa Abdelsamei Abde lHafez4; Salwa Faheem Mahmoud5; Mohamed El-Bayaa6; Dina S. El-kady7; Mervat Mostafa Omran8; 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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