Heterocyclization of Poly functionalized Pyrimidine: Novel Synthesis and Antiproliferative Evaluation of Azino and Azolo Pyrimidines | ||||
| Egyptian Journal of Chemistry | ||||
| Volume 66, Issue 1, January 2023, Page 239-248 PDF (1.03 MB) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2022.130304.5741 | ||||
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| Authors | ||||
Mohamed H Abd El-Azim1; Mohamed Assy2; Reham Galal3; Yasser Selim   4
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| 1Department of Chemistry, Faculty of Science, Zagazig University, Egypt. | ||||
| 2Chemistry Department, Faculty of Science, Zagazig University, ET-44519, Zagazig,, Egypt | ||||
| 3Zagazig University, Faculty of Science | ||||
| 4Chemistry Department, Faculty of Specific Education. Zagazig University | ||||
| Abstract | ||||
| Mercaptopyrimidin 1 was subjected to an acidic medium reaction with urea and aromatic aldehydes, yielding pyrimidopyrimidine 5a,b via unsaturated system 3, followed by 1,4 additions and subsequent H2S elimination. Using thiourea and/or guanidine instead of urea in the aforementioned process yielded pyrimidines of type (5 c-f). Condensation of benzaldehyde and its derivatives with compound 1 is followed by H-shift and oxidative cyclization, resulting in polycyclic compounds. 7. To make ozoloazines 9a-b, compound 7 undergoes a substitution reaction with urea and thiourea, followed by air oxidation. The cyclocondensation of hydrazides derivatives yielded triazolopyrimidines (12 a, b). In vitro, all novel pyrimidine derivatives were tested for antiproliferative activity against two cell lines: human gastric carcinoma (BGC-823) and human lung cancer (A-549). The results were compared to the NIH/3T3 murine fibroblast cell line. Some of these compounds, in particular 5a–f, 6,8,10a-b and 12a-b, were discovered to be the most effective derivatives against all cancer cell lines, with no impact on normal cells. Using the structure–activity connection as a guide, compound 10b has a greater activity against A-549 cells (IC50= 14.15 0.33 g/ml), as it contains thiadiazolidine imine nucleus which attached to thio pyran ring. | ||||
| Keywords | ||||
| Azino pyrimidines; azolo pyrimidines; pyrimidopyrimidine; antitumor agents | ||||
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