Synthesis and Characterization of Macrocyclic Chiral Tröger’s Base Phenhomazine Candidates as Anticancer Agent
| Autor: | Alhussein A. Ibrahim, Korany A. Ali, Naglaa A. Abdel Hafez, Mohamed A. Elsayed, Khalid M. H. Mohamed, Hanaa M. Hosni, Abd El-Galil E. Amr, Elsayed A. Elsayed |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Frontiers in Chemistry, Vol 8 (2021) |
| Druh dokumentu: | article |
| ISSN: | 2296-2646 72222476 |
| DOI: | 10.3389/fchem.2020.633065 |
| Popis: | 1,4,7,10-Tetraoxa[10](2,8)trögerophane 5 was synthesized from its corresponding precursors. Heating of 2 with p-nitrophenoxide afforded bis(p-nitrophenyl)ether 3, which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether 4. Treatment of 4 with paraformaldehyde and triflouroacetic anhydride gave trögerophane 5. Reaction of 5 with trifluroacetic anhydride afforded phenhomazine derivative 6, which was treated with potassium carbonate to afford tetrahydrophenhomazine 7. Finally, reaction of 7 with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds 8, 9 and 10, respectively. The synthesized trögerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa[10](2,8)trögerophane had a promising selectivity towards colon cancer cell line with an IC50 of 92.7 µg/ml. |
| Databáze: | Directory of Open Access Journals |
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