Synthesis and Antimicrobial Activity of Novel Azolopyrimidines and Pyrido-Triazolo-Pyrimidinones Incorporating Pyrazole Moiety

Abbas I.M.; Abdallah M.A.; Gomha S.M.; Kazem M.S.H.

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Synthesis and Antimicrobial Activity of Novel Azolopyrimidines and Pyrido-Triazolo-Pyrimidinones Incorporating Pyrazole Moiety

Abbas I.M.; Abdallah M.A.; Gomha S.M.; Kazem M.S.H.

Full Text link: https://t.ly/0EE9g

Date issued: 2017

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Doi: https://doi.org/10.1002/jhet.2968 PubMed ID :

Publisher: HeteroCorporation

Series Info: Journal of Heterocyclic Chemistry
54

Type: Article

Keywords: 1 (pyrazol 3 yl) 2 propenone , 3 cinnamoyl 5 methyl 1 phenyl 1h pyrazole 4 carboxylate , 7 (pyrazolyl) 2 thioxo 5 phenyl 1,3 dihydropyrido[2,3 d]pyrimidin 4 one , acetic acid , azolopyrimidine derivative , ethyl 1,5 diphenyl 3 [2 phenyl 1,2 dihydrobenzo[4,5] imidazo[1,2 a]pyrimidin 4 yl]1h pyrazole 4 carboxylate , ethyl 1,5 diphenyl 3 [2 phenyl 2H benzo[4,5]thiazolo[3,2 a] pyrimidin 4 yl] 1h pyrazole 4 carboxylate , ethyl 1,5 diphenyl 3 [2 phenyl 2h pyrimido(1,2 a) pyrimidin 4 yl] 1h pyrazole 4 carboxylate , ethyl 1,5 diphenyl 3 [5 phenyl 4,5 dihydro [1,2,4]triazolo [1,5 a]pyrimidin 7 yl] 1h pyrazole 4 carboxylate , ethyl 1,5 diphenyl 3 [5 phenyl 4,5 dihydrotetrazolo [1,5 a]pyrimidin 7 yl] 1h pyrazole 4 carboxylate , ethyl 1,5 diphenyl 3 [7 phenyl 7h thiazolo(3,2 a)pyrimidin 5 yl] 1h pyrazole 4 carboxylate , ethyl 3 (2,5 diphenyl 4,5 dihydropyrazolo[1,5 a]pyrimidin 7 yl) 1,5 diphenyl 1h pyrazole 4 carboxylate , ethyl 3 [2 [(2,4 dioxopentan 3 yl)thio] 4 oxo 5 phenyl 3,4 dihydropyrido[2,3 d]pyrimidin 7 yl] 1,5 diphenyl 1h pyrazole 4 carboxylate , ethyl 3 [2 [[1,3 dioxo 1 (phenylamino)butan 2 yl]thio] 4 oxo 5 phenyl 3,4 dihydropyrido[2,3 d]pyrimidin 7 yl] 1,5 diphenyl 1h pyrazole 4 carboxylate , ethyl 5 methyl 1 phenyl 3 [2 phenyl 1,2 dihydrobenzo [4,5]imidazo[1,2 a]pyrimidin 4 yl] 1h pyrazole 4 carboxylate , ethyl 5 methyl 1 phenyl 3 [2 phenyl 2h benzo[4,5]thiazolo [3,2 a]pyrimidin 4 yl] 1h pyrazole 4 carboxylate , ethyl 5 methyl 1 phenyl 3 [2 phenyl 2h pyrimido(1,2 a) pyrimidin 4 yl] 1h pyrazole 4 carboxylate , ethyl 5 methyl 1 phenyl 3 [5 phenyl 4,5 dihydro [1,2,4]triazolo [1,5 a]pyrimidin 7 yl] 1h pyrazole 4 carboxylate , ethyl 5 methyl 1 phenyl 3 [5 phenyl 4,5 dihydrotetrazolo [1,5 a]pyrimidin 7 yl] 1h pyrazole 4 carboxylate , ethyl 5 methyl 1 phenyl 3 [7 phenyl 7h thiazolo(3,2 a) pyrimidin 5 yl] 1h pyrazole 4 carboxylate , heterocyclic amine , hydrazonoyl chloride , pyrazole , pyrido triazolo pyrimidinone derivative , pyridotriazolopyrimidine , pyrido[2,3 d][1,2,4]triazolo[4,3 a] pyrimidinone , pyrimidine derivative , pyrimidinone derivative , triethylamine , unclassified drug , unindexed drug , antimicrobial activity , Article , catalysis , drug mechanism , drug structure , elemental analysis , infrared spectroscopy , Klebsiella pneumoniae , mass spectrometry , nonhuman , proton nuclear magnetic resonance , spectroscopy , Staphylococcus aureus , synthesis

Abstract:

A new series of azolopyrimidine derivatives incorporating pyrazole moiety were synthesized by reaction of 1-(pyrazol-3-yl)-2-propenone with a number of heterocyclic amines in the presence of a catalytic amount of acetic acid. The mechanism of formation of the products was also discussed, and the structure assigned was elucidated based on both elemental and spectral analyses data. In addition, 7-(pyrazolyl)-2-thioxo-5-phenyl-1,3-dihydropyrido[2,3-d]pyrimidin-4-one was used as starting material for preparation of a new series of pyridotriazolopyrimidines via its reaction with a variety of hydrazonoyl chlorides in dioxane using triethylamines as catalyst. The assigned structure for these products was also proved via elemental analysis and spectroscopic techniques (IR, 1H NMR, and Mass). Moreover, the antimicrobial activity of some selected examples of the new products was evaluated, and the results obtained revealed high activity of compound 20a against the Gram positive bacteria Staphylococcus aureus and the Gram negative bacteria Klebsiella pneumonie. All the tested compounds have no antifungal activity. � 2017 Wiley Periodicals, Inc.