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

被引:13
作者
Zaki, Remon M. [1 ]
El-Dean, Adel M. Kamal [1 ]
Radwan, Shaban M. [1 ]
Abd ul-Malik, Mokhtar A. [1 ,2 ]
机构
[1] Assiut Univ, Fac Sci, Chem Dept, POB 71516, Assiut 71516, Egypt
[2] Taiz Univ, Fac Appl Sci, Chem Dept, Taizi, Yemen
关键词
Thienopyrazolopyrazine; pyrimidine; triazole; triazepine; synthesis; antimicrobial activity; anti-inflammatory activity; POLYESTER FIBERS; DRUGS; DERIVATIVES; THERAPY;
D O I
10.2174/1570179415666180607105627
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aim and Objective: We reported in this manuscript, synthesis of novel pyrazolopyrazinothieno-pyrimidines. 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.
引用
收藏
页码:863 / 871
页数:9
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