Synthesis and antibacterial activity of N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl)piperazinyl quinolone derivatives

• Published in: Bioorganic & medicinal chemistry letters Vol. 15; no. 20; pp. 4488 - 4492
• Main Authors: Foroumadi, Alireza, Emami, Saeed, Hassanzadeh, Abdolreza, Rajaee, Majid, Sokhanvar, Kazem, Moshafi, Mohammad Hassan, Shafiee, Abbas
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15-10-2005; Elsevier
• Subjects: 1,3,4-Thiadiazole; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Biological and medical sciences; Medical sciences; Microbial Sensitivity Tests; Pharmacology. Drug treatments; Quinolone; Quinolones - chemical synthesis; Quinolones - pharmacology; Staphylococcus aureus; Staphylococcus aureus - drug effects; Staphylococcus epidermidis; Staphylococcus epidermidis - drug effects; Structure-Activity Relationship; Antibacterial activity; Quinolone; 1,3,4-Thiadiazole; Nitro compound; Sulfur nitrogen heterocycle; Nitrogen heterocycle; Benzene derivatives; Thiadiazole derivatives; In vitro; Fluoroquinolone derivatives; Staphylococcus epidermidis; Structure activity relation; Gram positive bacteria; Bacteria; Micrococcales; Micrococcaceae; Piperazine derivatives; Antibacterial agent; Chemical synthesis; Quinolone derivatives; Staphylococcus aureus
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2005.07.016

A series of
N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and
N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl) derivatives of piperazinyl quinolones was synthesized and evaluated for antibacterial activity. Some of these derivatives exhibit comparable or more potent activity against Gram-positive bacteria;
Staphylococcus aureus and
Staphylococcus epidermis, with respect to the reference drugs. The SAR of this series indicates that both the structure of the benzyl unit and the S or SO
2 linker dramatically impact antibacterial activity.
A series of
N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and
N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl) derivatives of piperazinyl quinolones was synthesized and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. Some of these derivatives exhibit high activity against Gram-positive bacteria;
Staphylococcus aureus and
Staphylococcus epidermidis, comparable or more potent than their parent
N-piperazinyl quinolones norfloxacin and ciprofloxacin as reference drugs. The SAR of this series indicates that both the structure of the benzyl unit and the S or SO
2 linker dramatically impact antibacterial activity.