Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agent
Abstract Background Described a series of main target compounds pyrimido[5,4-e][1,2,4]triazines is obtained via condensation of 6-hydrazinyluracil with different aromatic aldehydes to give the hydrazones followed by nitrosation with HNO2 then intramolecular cyclization. On the other hand, pyrazolopy...
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| Format: | Article |
| Language: | English |
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BMC
2018-05-01
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| Series: | Chemistry Central Journal |
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| Online Access: | http://link.springer.com/article/10.1186/s13065-018-0424-3 |
| _version_ | 1818717596081455104 |
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| author | Samar A. El-Kalyoubi |
| author_facet | Samar A. El-Kalyoubi |
| author_sort | Samar A. El-Kalyoubi |
| collection | DOAJ |
| description | Abstract Background Described a series of main target compounds pyrimido[5,4-e][1,2,4]triazines is obtained via condensation of 6-hydrazinyluracil with different aromatic aldehydes to give the hydrazones followed by nitrosation with HNO2 then intramolecular cyclization. On the other hand, pyrazolopyrimidines can be obtained by the reaction of hydrazones with dimethylformamide-dimethylacetal (DMF-DMA), DMF-DMA in the presence of DMF or by refluxing the hydrazinyluracil with DMF-DMA in the presence of DMF directly. The newly synthesized compounds are evaluated in vitro for their anticancer activity against human lung carcinoma (A549). Results A newly substituted compounds of benzaldehyde-pyrimidin-4-yl)hydrazones (5a–f), pyrimido[5,4-e][1,2,4]triazines 6a–e, arylethylidenehydrazinylpyrimidine 7a,b and pyrazolopyrimidines 9,11 are screened for cytotoxic activity against human lung carcinoma (A549) cell line. They exhibited a good yield. Compound 6b shows the highest effect with IC50 value 3.6 μM, followed by compounds 9, 5a, 8, 5e, 6e, 5b, 5f, 7a, 5c, 6c, 7b, 6a, 11, 5d and 6d. Conclusion A simple and efficient route is used for the synthesis of pyrimido[5,4-e][1,2,4]triazines and pyrazolopyrimidines. The synthesized compounds are screened for antitumor activity. |
| first_indexed | 2024-12-17T19:37:40Z |
| format | Article |
| id | doaj.art-03098a21b27c49ec8a77cc0e88ef2e38 |
| institution | Directory Open Access Journal |
| issn | 1752-153X |
| language | English |
| last_indexed | 2024-12-17T19:37:40Z |
| publishDate | 2018-05-01 |
| publisher | BMC |
| record_format | Article |
| series | Chemistry Central Journal |
| spelling | doaj.art-03098a21b27c49ec8a77cc0e88ef2e382022-12-21T21:35:06ZengBMCChemistry Central Journal1752-153X2018-05-0112111410.1186/s13065-018-0424-3Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agentSamar A. El-Kalyoubi0Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy (Girls), Al-Azhar UniversityAbstract Background Described a series of main target compounds pyrimido[5,4-e][1,2,4]triazines is obtained via condensation of 6-hydrazinyluracil with different aromatic aldehydes to give the hydrazones followed by nitrosation with HNO2 then intramolecular cyclization. On the other hand, pyrazolopyrimidines can be obtained by the reaction of hydrazones with dimethylformamide-dimethylacetal (DMF-DMA), DMF-DMA in the presence of DMF or by refluxing the hydrazinyluracil with DMF-DMA in the presence of DMF directly. The newly synthesized compounds are evaluated in vitro for their anticancer activity against human lung carcinoma (A549). Results A newly substituted compounds of benzaldehyde-pyrimidin-4-yl)hydrazones (5a–f), pyrimido[5,4-e][1,2,4]triazines 6a–e, arylethylidenehydrazinylpyrimidine 7a,b and pyrazolopyrimidines 9,11 are screened for cytotoxic activity against human lung carcinoma (A549) cell line. They exhibited a good yield. Compound 6b shows the highest effect with IC50 value 3.6 μM, followed by compounds 9, 5a, 8, 5e, 6e, 5b, 5f, 7a, 5c, 6c, 7b, 6a, 11, 5d and 6d. Conclusion A simple and efficient route is used for the synthesis of pyrimido[5,4-e][1,2,4]triazines and pyrazolopyrimidines. The synthesized compounds are screened for antitumor activity.http://link.springer.com/article/10.1186/s13065-018-0424-36-HydrazinyluracilPyrimidotriazinePyrazolopyrimidineDimethylformamide-dimethylacetalAnticancer activities |
| spellingShingle | Samar A. El-Kalyoubi Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agent Chemistry Central Journal 6-Hydrazinyluracil Pyrimidotriazine Pyrazolopyrimidine Dimethylformamide-dimethylacetal Anticancer activities |
| title | Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agent |
| title_full | Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agent |
| title_fullStr | Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agent |
| title_full_unstemmed | Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agent |
| title_short | Synthesis and anticancer evaluation of some novel pyrimido[5,4-e][1,2,4]triazines and pyrazolo[3,4-d]pyrimidine using DMF-DMA as methylating and cyclizing agent |
| title_sort | synthesis and anticancer evaluation of some novel pyrimido 5 4 e 1 2 4 triazines and pyrazolo 3 4 d pyrimidine using dmf dma as methylating and cyclizing agent |
| topic | 6-Hydrazinyluracil Pyrimidotriazine Pyrazolopyrimidine Dimethylformamide-dimethylacetal Anticancer activities |
| url | http://link.springer.com/article/10.1186/s13065-018-0424-3 |
| work_keys_str_mv | AT samaraelkalyoubi synthesisandanticancerevaluationofsomenovelpyrimido54e124triazinesandpyrazolo34dpyrimidineusingdmfdmaasmethylatingandcyclizingagent |