title: Synthesis and molecular modeling of antimicrobial active fluoroquinolone-pyrazine conjugates with amino acid linkers.
abstract: Novel fluoroquinolone-pyrazine conjugates 7a-h with amino acid linkers were synthesized in good yields utilizing benzotriazole chemistry. Antimicrobial bioassay showed that the synthesized bis-conjugates have antimicrobial properties comparable to the parent drugs. Compound 7h showed superior antibacterial activity against Staphylococcus aureus and Streptococcus pyogenes (MIC=74.6 μM and 149.3 μM, respectively). This matched well with the estimated values obtained from 3D-pharmacophore and 2D-QSAR studies (MIC=67 μM and 92.9 μM, respectively).
authors.affiliation: Department of Chemistry & Physics, Augusta University, Augusta, GA 30912, USA. Electronic address: sspanda12@gmail.com.
authors.forename: Siva S
authors.initials: SS
authors.lastname: Panda
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
authors.forename: Oleksandr S
authors.initials: OS
authors.lastname: Detistov
authors.affiliation: Pesticide Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt.
authors.forename: Adel S
authors.initials: AS
authors.lastname: Girgis
authors.affiliation: Department of Chemistry & Physics, Augusta University, Augusta, GA 30912, USA.
authors.forename: Prabhu P
authors.initials: PP
authors.lastname: Mohapatra
authors.affiliation: Microbiology Department, Faculty of Veterinary Medicine, Cairo University, Cairo, Egypt.
authors.forename: Ahmed
authors.initials: A
authors.lastname: Samir
authors.affiliation: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
authors.forename: Alan R
authors.initials: AR
authors.lastname: Katritzky
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D024841:Fluoroquinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D021281:Quantitative Structure-Activity Relationship; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D012485:Salmonella typhi / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013297:Streptococcus pyogenes / Q000187:drug effects; D014230:Triazoles / Q000737:chemistry
chemical_list: C000621355:1-cyclopropyl-6-fluoro-4-oxo-7-(4-(4-(pyrazine-2-carboxamido)butanoyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid; D000596:Amino Acids; D000900:Anti-Bacterial Agents; D024841:Fluoroquinolones; D010879:Piperazines; D011719:Pyrazines; D011804:Quinolines; D014230:Triazoles
keywords: Antibiotics; Benzotriazole chemistry; Computational studies; Conjugates