Synthesis and antibacterial activity of N-[5-(chlorobenzylthio)-1,3,4-thiadiazol-2-yl] piperazinyl quinolone derivatives.
A series of N-[5-(chlorobenzylthio)-1,3,4-thiadiazol-2-yl] piperazinyl quinolone derivatives (4a-I) have been synthesized by reaction of piperazinyl quinolones with 5-chloro-2-(chlorobenzylthio)-1,3,4-thiadiazoles. Their structures were confirmed by elemental analysis, IR and NMR spectra. The antibacterial activities of 4a-I against a variety of Gram-positive and Gram-negative bacteria were determined. Several compounds showed a good antibacterial activity against Gram-positive bacteria among which, compound 4e with a 2-chlorobenzylthio moiety in ciprofloxacin derivative, exhibited high activities against Staphylococcus aureus and Staphylococcus epidermidis (MIC = 0.06 microg/mL). The structure-activity relationship (SAR) study revealed that the position of chlorine atom on benzyl moiety would dramatically affect the antibacterial activities of the synthesized compounds.
Foroumadi
Alireza
A
Pharmaceutical Sciences Research Center Tehran University of Medical Sciences, Tehran, Iran. aforoumadi@tums.ac.ir
Firoozpour
Loghman
L
Emami
Saeed
S
Mansouri
Shahla
S
Ebrahimabadi
Abdolrasoul H
AH
Asadipour
Ali
A
Amini
Mohsen
M
Saeid-Adeli
Nosratollah
N
Shafiee
Abbas
A
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015363:Quinolones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D010879:Piperazines; D015363:Quinolones; D013830:Thiadiazoles