Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinolineDerivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents
Eladasy, A., Hussein, A., Ishak, E., Hafiz, I., Gawish, E., Elapasery, M., El-Gaby, M. (2021). Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinolineDerivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents. EKB Journal Management System, 64(2), 913-921. doi: 10.21608/ejchem.2020.44466.2901
Abubaker A Eladasy; Abdelhaleem M Hussein; Esam A. Ishak; Ibrahim S. A. Hafiz; Emad H Gawish; Morsy Elapasery; Mohamed El-Gaby. "Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinolineDerivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents". EKB Journal Management System, 64, 2, 2021, 913-921. doi: 10.21608/ejchem.2020.44466.2901
Eladasy, A., Hussein, A., Ishak, E., Hafiz, I., Gawish, E., Elapasery, M., El-Gaby, M. (2021). 'Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinolineDerivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents', EKB Journal Management System, 64(2), pp. 913-921. doi: 10.21608/ejchem.2020.44466.2901
Eladasy, A., Hussein, A., Ishak, E., Hafiz, I., Gawish, E., Elapasery, M., El-Gaby, M. Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinolineDerivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents. EKB Journal Management System, 2021; 64(2): 913-921. doi: 10.21608/ejchem.2020.44466.2901

Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinolineDerivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents

Egyptian Journal of Chemistry
Article 32, Volume 64, Issue 2, February 2021, Page 913-921  XML PDF (637.94 K)
Document Type: Original Article
DOI: 10.21608/ejchem.2020.44466.2901
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Authors
Abubaker A Eladasy1; Abdelhaleem M Hussein2; Esam A. Ishak3; Ibrahim S. A. Hafiz4; Emad H Gawish3; Morsy Elapasery email orcid 5; Mohamed El-Gaby2
1Department of Chemistry, Faculty of Science, Al-Azhar University, Assiut, Egypt
2Department of Chemistry, Faculty of Science, Al Azhar University, Assiut 71524, Egypt
3Departmentof Chemistry, Faculty of Science, Al-AzharUniversity at Assiut, Assiut71524, Egypt.
4Department of Chemistry, Faculty of Education, Suez CanalUniversity, Al-Arish, Egypt.
5Dyeing, Printing and Auxiliaries Department, Textile Research Division, National Research Centre, Cairo 12622, Egypt
Abstract
Hydrazone derivative (3) was used as a precursor for the synthesis of novel [1,2,4]triazolo[1,5-a]pyridine deivatives via its reaction with some electrophilic reagents. Treatment of hydrazone derivative (3) with arylidenemalononitriles(4) in the presence of piperidine afforded the 1,2,4-triazolo[1,5-a]pyridine derivatives (7a-d). Ternary condensation of hydrazone (3), aliphatic aldehyde and malononitrile (1:1:1 molar ratio) in the presence of a basic catalyst furnished the novel 1,2,4-triazolo[1,5-a]pyridine derivatives (8a,b). Similarly, cyclization of hydrazone (3) with ethyl α-cyanocinnamates (9) (1:1 molar ratio) yields the corresponding 1,2,4-triazolo[1,5-a]pyridines (10a-c). The hydrazone (3) can be cyclized with appropriate arylazomalononitriles(11) to afford the corresponding 1,2,4-triazolo[1,5-a]pyridines (14a,b). The behavior of fused thiophene derivative (15) towards electron-poor olefins was investigated. It is has been found that, 1,2,4-triazolo[1,5-a]isoquinoline derivative (17) was obtained by treatment of thiophene derivative (15) with dimethyl acetylenedicarboxylate (DMAD). Condensation of compound (15) with N-phenylmalemide furnished pyrrolotriazoloisoquinoline derivative (18). Also, the triazoloisoquinoline derivative (19) was obtained by condensation of compound (15) with chalcone. All the newly synthesized compounds were characterized by analytical and spectral data and evaluated for their antibacterial and antifungal activities in vitro against two Gram-positive bacteria, two Gram negative bacteria as well as two fungi. In general, the newly synthesized compounds showed good antimicrobial activities.
Keywords
cyanoacetic acid hydrazide; hydrazone; arylidenemalononitrile; Antimicrobial activity
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