title: Design synthesis and antibacterial activity studies of new thiadiazoloquinolone compounds.
abstract: Abstract New 9-(alkyl/aryl)-4-fluoro-6-oxo[1,2,5]thiadiazolo[3,4-h]quinoline-5-carboxylic acids and their esters were designed and synthesized. A detailed discussion of the reactions utilized in the preparation of the intermediate and target compounds is reported. All the newly synthesized compounds were fully characterized using all the physico-chemical means needed. All the intermediates and the final esters and acids were tested against bacterial and fungal strains. The acids 25a and 25c proved to be very active against Gram positive and Gram negative bacteria with MIC 0.15-3 µg/mL. The structure-activity relationship of antibacterial thiadiazoloquinolones shows that compounds 25a and 25c are twice less potent than the corresponding cyclopropyl derivative 16. Therefore, the cyclopropyl moiety on N-9 seems to be the most suitable substituent.
authors: Chemistry Department, Faculty of Science, The University of Jordan , Amman , Jordan .
authors: Raed A
authors: RA
authors: Al-Qawasmeh
authors: Mohammed M
authors: MM
authors: Abadleh
authors: Jalal A
authors: JA
authors: Zahra
authors: Mustafa M
authors: MM
authors: El-Abadelah
authors: Rabab
authors: R
authors: Albashiti
authors: Franca
authors: F
authors: Zani
authors: Matteo
authors: M
authors: Incerti
authors: Paola
authors: P
authors: Vicini
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001234:Aspergillus niger / Q000187:drug effects / Q000254:growth & development; D001412:Bacillus subtilis / Q000187:drug effects / Q000254:growth & development; D041022:Candida tropicalis / Q000187:drug effects / Q000254:growth & development; D015195:Drug Design; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D006193:Haemophilus influenzae / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000254:growth & development; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D015363:Quinolones; D013844:Thiazoles
keywords: 6-Fluoroquinolone; antibacterial activity; synthesis; thiadiazoloquinolone