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Design, Synthesis, Molecular Modeling Study, and Antimicrobial Activity of Some Novel Pyrano[2,3‐ b ]pyridine and Pyrrolo[2,3‐ b ]pyrano[2.3‐ d ]pyridine Derivatives
Author(s) -
Elkanzi Nadia A. A.,
Bakr Rania B.,
Ghoneim Amira A.
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3412
Subject(s) - chemistry , antimicrobial , pyridine , aspergillus niger , stereochemistry , escherichia coli , enzyme , docking (animal) , staphylococcus aureus , combinatorial chemistry , bacteria , biochemistry , organic chemistry , medicine , nursing , gene , genetics , biology
Novel derivatives of pyrano[2,3‐ b ]pyridine and pyrrolo[2,3‐ b ]pyrano[2.3‐ d ]pyridine were prepared, and their structures were elucidated by spectral and elemental analyses. The newly prepared candidates were evaluated for their antimicrobial activity against Candida sp ., Aspergillus multi , Aspergillus niger , Escherichia coli , and Staphylococcus aureus . All the tested compounds revealed potent to moderate activity toward all tested microorganisms; especially, candidate 10 showed comparable antifungal activity as that showed by the standard drug ketoconazole toward Candida sp ., and ethyl 4‐methyl‐1,7,8,9‐tetrahydropyrano[2,3‐ b ]pyrrolo[2,3‐ d ]pyridine‐3‐carboxylate ( 12 ) was the most active compound against all the tested bacteria. Furthermore, the newly synthesized compounds are subjected to molecular docking study for the inhibition of the enzyme L‐glutamine: D‐fructose‐6‐phosphate amidotransferase [GlcN‐6‐P], which is a new target for antimicrobials to explain action mode of these target compounds as leads for discovering other antimicrobial agents.