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A Convenient Synthesis, Reactions and Biological Activities of Some Novel Thieno[3,2-e]pyrazolo[3,4-b]pyrazine Compounds as Anti-microbial and Antiinflammatory Agents

[ Vol. 15 , Issue. 6 ]

Author(s):

Remon M. Zaki*, Remon M. Zaki*, Adel M. Kamal El-Dean, Adel M. Kamal El-Dean, Shaban M. Radwan, Shaban M. Radwan, Mokhtar A. Abd ul-Malik and Mokhtar A. Abd ul-Malik   Pages 863 - 871 ( 9 )

Abstract:


Aim and Objective: We reported in this manuscript, synthesis of novel pyrazolopyrazinothienopyrimidines. The o-amino-thienopyrazolopyrazine-carbonitrile 4 was used as a versatile precursor for synthesis of new heterocyclic compounds. Due to development of resistance to the current antimicrobial therapy and non-steroidal anti-inflammatory drugs (NSAIDs), continues research for more effective agents is interesting. Hence, the suspected promising biological activities of pyrazolopyrazine compounds persuaded us to study the anti-microbial and anti-inflammatory activities in comparison with standard drugs.

Materials and Methods: The chemical structures of the newly synthesized compounds were confirmed by elemental and spectral analyses. Activities of the synthesized compounds against a number of Gram-negative and Gram-positive bacterial strains were investigated. The fungal strains were obtained from some cases of human dermatophytosis. The antimicrobial activities were determined according to the Kwon-Chung and Bennett method. Anti-inflammatory activity was evaluated using carrageenan induced paw edema method.

Results: The antibacterial screening of the synthesized compounds represented that the o-amino-carbonitrile 4 and triazepinone 11 have the highest activity towards E. coli & S. aureus and S. pneumonia. The amino-imino 6 was very effective against E. coli. Ring closure of 6 to triazolopyrimidine 7 increases the antibacterial activity against E. coli & K. pneumonia, their inhibition zones were higher than ciprofloxacin. Also, the triazolopyrimidines 7 and 10 exhibited high antifungal activity against all tested strains. Compounds 6 and 11 revealed high antifungal activity against S. racemosum and T. rubrum. The anti-inflammatory activity data indicated that all the tested compounds 4, 6, 7, 10 & 11 revealed the highest anti-inflammatory effect after 4 hrs. of carrageenan injection.

Conclusion: we found that most of the examined novel thieno- pyrazolopyrazine compounds exhibited promising antibacterial, antifungal and anti-inflammatory activities which can be used as potential antibacterial, antifungal and anti-inflammatory drugs.

Keywords:

Thienopyrazolopyrazine, pyrimidine, triazole, triazepine, synthesis, antimicrobial activity, anti-inflammatory activity., Thienopyrazolopyrazine, pyrimidine, triazole, triazepine, synthesis, antimicrobial activity, anti-inflammatory activity.

Affiliation:

Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516

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