Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents
As a part of systematic investigation of the synthesis and biological activities of pyrazole analogues linked to various heterocyclic systems, a new series of pyrazolo-N-glycoside derivatives, pyrazolopyranopyrimidine and C-glycoside of pyrazolopyranotriazolo-pyrimidine derivatives was synthesized t...
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| Format: | Article |
| Language: | English |
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Sciendo
2015-09-01
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| Series: | Acta Pharmaceutica |
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| Online Access: | https://doi.org/10.1515/acph-2015-0022 |
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| author | Hafez Hend N. El-Gazzar Abdel-Rhman B. A. |
| author_facet | Hafez Hend N. El-Gazzar Abdel-Rhman B. A. |
| author_sort | Hafez Hend N. |
| collection | DOAJ |
| description | As a part of systematic investigation of the synthesis and biological activities of pyrazole analogues linked to various heterocyclic systems, a new series of pyrazolo-N-glycoside derivatives, pyrazolopyranopyrimidine and C-glycoside of pyrazolopyranotriazolo-pyrimidine derivatives was synthesized through the reaction of the key intermediate 6-amino-3-methyl-4-(substituted-phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (3a,b) with different reagents. Structures of the newly synthesized compounds were elucidated by elemental microanalysis and spectroscopic methods. The compounds were subjected to in vitro antitumor evaluation using the MTT assay. N-(β-D-ribofuranosyl)- and N-(β-D-xylofuranosyl)-6{[(1E)-4-chlorophenyl)-methylene] amino}4-(4-florophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile (6a,b) were the most active compounds against three human cancer cell lines. Also, most of the newly synthesized compounds exhibited high activity towards Gram-negative and Gram-positive bacteria. Compound 6a exhibited excellent activity towards bacteria compared to ofloxacine as the reference drug. |
| format | Article |
| id | doaj-art-5e3fa55dcfc04bdeab12ed31143a1da3 |
| institution | Kabale University |
| issn | 1846-9558 |
| language | English |
| publishDate | 2015-09-01 |
| publisher | Sciendo |
| record_format | Article |
| series | Acta Pharmaceutica |
| spelling | doaj-art-5e3fa55dcfc04bdeab12ed31143a1da32025-02-02T15:49:18ZengSciendoActa Pharmaceutica1846-95582015-09-0165321523310.1515/acph-2015-0022acph-2015-0022Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agentsHafez Hend N.0El-Gazzar Abdel-Rhman B. A.1 Al-Imam Mohammad Ibn Saud Islamic University (IMSIU), Faculty of Science, Department of Chemistry, P.O. Box 90950 Riyadh, 11623, Kingdom of Saudi Arabia Al-Imam Mohammad Ibn Saud Islamic University (IMSIU), Faculty of Science, Department of Chemistry, P.O. Box 90950 Riyadh, 11623, Kingdom of Saudi ArabiaAs a part of systematic investigation of the synthesis and biological activities of pyrazole analogues linked to various heterocyclic systems, a new series of pyrazolo-N-glycoside derivatives, pyrazolopyranopyrimidine and C-glycoside of pyrazolopyranotriazolo-pyrimidine derivatives was synthesized through the reaction of the key intermediate 6-amino-3-methyl-4-(substituted-phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (3a,b) with different reagents. Structures of the newly synthesized compounds were elucidated by elemental microanalysis and spectroscopic methods. The compounds were subjected to in vitro antitumor evaluation using the MTT assay. N-(β-D-ribofuranosyl)- and N-(β-D-xylofuranosyl)-6{[(1E)-4-chlorophenyl)-methylene] amino}4-(4-florophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile (6a,b) were the most active compounds against three human cancer cell lines. Also, most of the newly synthesized compounds exhibited high activity towards Gram-negative and Gram-positive bacteria. Compound 6a exhibited excellent activity towards bacteria compared to ofloxacine as the reference drug.https://doi.org/10.1515/acph-2015-0022n-nucleoside of pyranopyrazolec-glycoside of pyrazolopyranotriazolopyrimidineanticancer activityantimicrobial activity |
| spellingShingle | Hafez Hend N. El-Gazzar Abdel-Rhman B. A. Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents Acta Pharmaceutica n-nucleoside of pyranopyrazole c-glycoside of pyrazolopyranotriazolopyrimidine anticancer activity antimicrobial activity |
| title | Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents |
| title_full | Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents |
| title_fullStr | Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents |
| title_full_unstemmed | Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents |
| title_short | Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents |
| title_sort | synthesis of pyranopyrazolo n glycoside and pyrazolopyranopyrimidine c glycoside derivatives as promising antitumor and antimicrobial agents |
| topic | n-nucleoside of pyranopyrazole c-glycoside of pyrazolopyranotriazolopyrimidine anticancer activity antimicrobial activity |
| url | https://doi.org/10.1515/acph-2015-0022 |
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