<abstract xml:lang="en" xmlns="http://www.w3.org/1999/xhtml"><p>New series of 2-hydrazino-7,8-dihydro-6<italic>H</italic>-cyclopenta[5,6] pyrido[2,3-<italic>d</italic>]pyrimidines and its 1,7,8,9-tetrahydrocyclopenta[5,6]pyrido[2,3-<italic>d</italic>][1,2,4]triazolo[4,3-<italic>a</italic>]pyrimidine, 1,7,8,9-tetrahydrocyclopenta[5,6]pyrido[2,3-<italic>d</italic>][1,2,3,4]tetrazolo[4,5-<italic>a</italic>]pyrimidine, 8,9-dihydro-7<italic>H</italic>-cyclopenta[5,6]pyrido[2,3-<italic>d</italic>]imidazolo[1,2-<italic>a</italic>]pyrimidine, 2-(pyrazol-1-yl)-7,8-dihydro-6<italic>H</italic>-cyclopenta[5,6]pyrido[2,3-<italic>d</italic>]pyrimidine derivatives were prepared in order to obtain new compounds with potential anti-inflammatory and analgesic activity and low ulcerogenic effect. The compounds possessing potent anti-inflammatory activity were further tested for their analgesic and ulcerogenic activities. Compounds 3-amino-6-(4-aryl)-9-(4-arylmethylene)-cyclopenta[5,6]pyrido[2,3-<italic>d</italic>][1,2,4]triazolo[4,3-<italic>a</italic>]pyrimidin-5(<italic>H</italic>)-one (<bold>4c</bold>), 1-amino-2-methyl-6-(4-aryl)-9-(4-aryl-methylene)-cyclopenta[5,6]pyrido[2,3-<italic>d</italic>]imidazolo[1,2-<italic>a</italic>]pyrimidin-5(<italic>H</italic>)-one (<bold>6a</bold>), 2-amino-5-(4-aryl)-8-(4-arylmethylene)-cyclopenta[5,6]pyrido-[2,3-<italic>d</italic>]pyrimidine-4(<italic>H</italic>)-one (9), 2-(3-amino-5-hydroxypyrazol- 1-yl)-5-(4-aryl)-8-(4-arylmethylene)-cyclopenta[5,6]-pyrido[2,3-<italic>d</italic>]pyrimidin-4(<italic>H</italic>)-one (<bold>10a</bold>) and 3-thioxo-6-(4-aryl)-9-(4-arylmethylene)-cyclopenta[5,6]pyrido[2,3-<italic>d</italic>]-[1,2,4]triazolo[4,3-<italic>a</italic>]pyrimidin-5(<italic>H</italic>)-one (13) showed significant analgesic effects. Compound 2-(3-amino-5-hydroxypyrazol-1-yl)-5-(4-aryl)-8-(4-arylmethylene)-cyclopenta [5,6]pyrido[2,3-<italic>d</italic>]pyrimidin-4(<italic>H</italic>)-one (<bold>10a</bold>) was evaluated as the lead compound having higher anti-inflammatory activity (82.8%) than ibuprofen (79.5%) and lower ulcerogenic effect.</p></abstract>

New series of 2-hydrazino-7,8-dihydro-6H-cyclopenta[5,6] pyrido[2,3-d]pyrimidines and its 1,7,8,9-tetrahydrocyclopenta[5,6]pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine, 1,7,8,9-tetrahydrocyclopenta[5,6]pyrido[2,3-d][1,2,3,4]tetrazolo[4,5-a]pyrimidine, 8,9-dihydro-7H-cyclopenta[5,6]pyrido[2,3-d]imidazolo[1,2-a]pyrimidine, 2-(pyrazol-1-yl)-7,8-dihydro-6H-cyclopenta[5,6]pyrido[2,3-d]pyrimidine derivatives were prepared in order to obtain new compounds with potential anti-inflammatory and analgesic activity and low ulcerogenic effect. The compounds possessing potent anti-inflammatory activity were further tested for their analgesic and ulcerogenic activities. Compounds 3-amino-6-(4-aryl)-9-(4-arylmethylene)-cyclopenta[5,6]pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(H)-one (4c), 1-amino-2-methyl-6-(4-aryl)-9-(4-aryl-methylene)-cyclopenta[5,6]pyrido[2,3-d]imidazolo[1,2-a]pyrimidin-5(H)-one (6a), 2-amino-5-(4-aryl)-8-(4-arylmethylene)-cyclopenta[5,6]pyrido-[2,3-d]pyrimidine-4(H)-one (9), 2-(3-amino-5-hydroxypyrazol- 1-yl)-5-(4-aryl)-8-(4-arylmethylene)-cyclopenta[5,6]-pyrido[2,3-d]pyrimidin-4(H)-one (10a) and 3-thioxo-6-(4-aryl)-9-(4-arylmethylene)-cyclopenta[5,6]pyrido[2,3-d]-[1,2,4]triazolo[4,3-a]pyrimidin-5(H)-one (13) showed significant analgesic effects. Compound 2-(3-amino-5-hydroxypyrazol-1-yl)-5-(4-aryl)-8-(4-arylmethylene)-cyclopenta [5,6]pyrido[2,3-d]pyrimidin-4(H)-one (10a) was evaluated as the lead compound having higher anti-inflammatory activity (82.8%) than ibuprofen (79.5%) and lower ulcerogenic effect.

Synthesis and evaluation of analgesic, anti-inflammatory and ulcerogenic activities of some triazolo- and 2-pyrazolyl-pyrido[2,3-<italic>d</italic>]-pyrimidines

National Research Centre, Photochemistry Department, Heterocyclic Unit, Dokki 12622 Cairo, Egypt

Acta Pharmaceutica

Synthesis and evaluation of analgesic, anti-inflammatory and ulcerogenic activities of some triazolo- and 2-pyrazolyl-pyrido[2,3-]-pyrimidines

New series of 2-hydrazino-7,8-dihydro-6H-cyclopenta[5,6] pyrido[2,3-d]pyrimidines and its...

Synthesis and evaluation of analgesic, anti-inflammatory and ulcerogenic activities of some triazolo- and 2-pyrazolyl-pyrido[2,3-d]-pyrimidines

Publié en ligne: 22 déc. 2008

Pages: 359 - 378

DOI: https://doi.org/10.2478/v10007-008-0024-1

Mots clés
pirido[2,3-]pirimidini, [1,2,4]triazol anelacija, protuupalno djelovanje, analgetsko djelovanje

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