<abstract xmlns="http://www.w3.org/1999/xhtml"><p>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-<italic>N</italic>-glycoside derivatives, pyrazolopyranopyrimidine and <italic>C</italic>-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-<italic>c</italic>]pyrazole-5-carbonitrile (<bold>3a,b</bold>) with different reagents. Structures of the newly synthesized compounds were elucidated by elemental microanalysis and spectroscopic methods. The compounds were subjected to <italic>in vitro</italic> antitumor evaluation using the MTT assay. <italic>N</italic>-(<italic>β</italic>-<italic>D</italic>-ribofuranosyl)- and <italic>N</italic>-(<italic>β</italic>-<italic>D</italic>-xylofuranosyl)-6{[(1<italic>E</italic>)-4-chlorophenyl)-methylene] amino}4-(4-florophenyl)-3-methyl-1,4-dihydropyrano[2,3-<italic>c</italic>]-pyrazole-5-carbonitrile (<bold>6a,b</bold>) 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 <bold>6a</bold> exhibited excellent activity towards bacteria compared to ofloxacine as the reference drug.</p></abstract>

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.

Synthesis of pyranopyrazolo <italic>N</italic>-glycoside and pyrazolopyranopyrimidine <italic>C</italic>-glycoside derivatives as promising antitumor and antimicrobial agents

Al-Imam Mohammad Ibn Saud Islamic University (IMSIU), Faculty of Science, Department of Chemistry, P.O. Box 90950 Riyadh, 11623, Kingdom of Saudi Arabia

Photochemistry Department, Heterocyclic and Nucleosides Unit, National Research Centre, Cairo, Egypt

Acta Pharmaceutica

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Synthesis of pyranopyrazolo -glycoside and pyrazolopyranopyrimidine -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...

Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents

Publié en ligne: 30 sept. 2015

Pages: 215 - 233

Accepté: 17 févr. 2015

DOI: https://doi.org/10.1515/acph-2015-0022

Mots clés
-nucleoside of pyranopyrazole, -glycoside of pyrazolopyranotriazolopyrimidine, anticancer activity, antimicrobial activity

© Hend N. Hafez et al.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents

Publié en ligne: 30 sept. 2015

Pages: 215 - 233

Accepté: 17 févr. 2015

DOI: https://doi.org/10.1515/acph-2015-0022

Mots clés-nucleoside of pyranopyrazole, -glycoside of pyrazolopyranotriazolopyrimidine, anticancer activity, antimicrobial activity

© Hend N. Hafez et al.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Mots clés
-nucleoside of pyranopyrazole, -glycoside of pyrazolopyranotriazolopyrimidine, anticancer activity, antimicrobial activity