Synthesis, Anticancer Activity and Molecular Docking Study of some New Thiazolo[2, 3-a]Pyrimidinedione-Based Heterocyclic Compounds | ||||
| Egyptian Journal of Chemistry | ||||
| Volume 66, Issue 3, March 2023, Page 79-90 PDF (1.06 MB) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2023.188464.7479 | ||||
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| Authors | ||||
Nesrin M. Morsy   1; Khadiga M. Abu-Zied 2; Hanem M. Awad 3
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| 1Organometallic and Organometalloid Chemistry Department,National Research Centre, Cairo,12622, Dokki, Egypt. | ||||
| 2Photochemistry Department, National Research Centre , Cairo, Dokki, 12622, Egypt. | ||||
| 3Tanning Materials and Leather Technology Department & Regulatory Toxicology Lab, Centre of Excellence, National Research Centre, Dokki 12622, Cairo, Egypt. | ||||
| Abstract | ||||
| New thiazolo[2,3-a] pyrimidinedione derivatives were synthesized by two different chemical methods.One method included the addition of a mixture of glacial acetic acid ,acetic anhydride (2 : 1), chloroacetic acid and anhydrous sodium acetate to mercapto-thieno[2,3-d]pyrimidinone derivatives 5aor 5b under reflux to give thieno[2,3-d]thiazolo[3,2-a]pyrimidinedione derivatives 6a or 6b which react with selected aldehydes 7,8, 9a-c,10,11at a next step to give our targeted products. The other method is the direct reaction of the solutions of 5a or 5b in the presence of the previous reagents except chloroacetic acid under reflux with series of aldehydes yielding the new derivatives7a, 7b, 8a, 8b, 9d, 9e, 9f, 9g, 9h,9i, 10a,10b,11a and11b. The chemical structure of these compounds was confirmed by various spectroscopic analysis. In vitro cytotoxic activity was investigated for all compounds against HCT-116, HepG2, and MCF-7 cancer cell lines. Two compounds were potent against all cell lines, 8a with IC50 4.7, 5.6, and 6.2 μM and9hwith IC50 5.4, 7.8, and 5.6 against HCT-116, HepG2, and MCF-7 respectively. Molecular docking against inosine monophosphate dehydrogenase2 showed that compound 8a had the top ranked free energy of binding ΔG -8.68 (kcal/mol) and RMSD 1.2 Å. | ||||
| Keywords | ||||
| Synthesis; Thiazolo[3,2-a]pyrimidinedione; Aldehyde; Anticancer Activity; Molecular Docking | ||||
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