Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents

Al-Trawneh, Salah A.; Zahra, Jalal A.; Kamal, Marwan R.; El‐Abadelah, Mustafa M.; Zani, Franca; Incerti, Matteo; Cavazzoni, Andrea; Alfieri, Roberta; Petronini, Pier Giorgio; Vicini, Paola

doi:10.1016/j.bmc.2010.06.098

Cited by 68 publications

(32 citation statements)

References 38 publications

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“…Fluoroquinolones were widely used in human and veterinary medicine for the treatment of infectious diseases [5][6][7]. Ciprofloxacin, a fluoroquinolone antibacterial agent [8,9], has a wide range of antibacterial activity, which is highly active against various Gram-positive and Gram-negative bacteria.…”

Section: Introductionmentioning

confidence: 99%

Structures and Antibacterial Properties of PLA-based Ciprofloxacin Composite Films Deposited by Low-Electron Beam Dispersion

Jiang

et al. 2020

Eurasian Chem. Tech. J.

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Polylactic acid (PLA)-based ciprofloxacin (Cip) antibacterial films with mass ratio PLA:Cip=1:1 were prepared by low-electron beam dispersion (EBD). The molecular structure, chemical composition and morphology of PLA-based ciprofloxacin antibacterial films were investigated by XPS, FTIR, liquid NMR and SEM. The antibacterial activity of composite films was tested against E. coli ATCC 25922 and S. aureus ATCC 12600 using the agar diffusion method on the solid LB agar medium. XPS and FTIR analysis showed the presence of an antibacterial ingredient in the composite films. Using NMR, it has been shown that the molecular structure of a monolayer of ciprofloxacin is fully consistent with the molecular structure of the initial ciprofloxacin powder. High antibacterial activity of the composite films has been also established and the layers still possess antibacterial activity with regard to S. aureus even after 7 days of leaching in an isotonic solution. The thermal treatment indicates that the composite films can withstand temperatures of 180 °C and keep its structure unchanged.

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Section: Introductionmentioning

confidence: 99%

Structures and Antibacterial Properties of PLA-based Ciprofloxacin Composite Films Deposited by Low-Electron Beam Dispersion

Jiang

et al. 2020

Eurasian Chem. Tech. J.

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“…15 Recently, the synthesis of fluoroquinolones has become of increasing interest since the quinoline skeleton is present in many chemotherapeutic agents. [16][17][18] These findings prompted us to explore the combination of an oxazole nucleus and fluorine atom within the pyranoquinolinone moiety in one molecular framework. In continuation of our research focused on the chemistry of pyrano [3,2-c]quinolinedione derivatives, 19,20 we now disclose the preparation of a new synthetically valuable 3-aminopyranoquinolone derivative in order to obtain a novel series of pyranoquinolinones incorporating an oxazole and/or fluorophenyloxazole at face c. We hope that these new compounds will have useful biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel oxazolopyranoquinolinones from 3-amino-4‐hydroxypyrano[3,2-c]quinolindione

Hassanin¹,

Abdou²,

Saeed³

2017

Arkivoc

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Abstract6-n-Butyl-3-nitropyrano[3,2-c]quinolinone was chemoselectively reduced to an amine derivative in a good yield (70%) using an efficient and simple tin-hydrochloric acid reaction. The novel 3-aminopyranoquinolinone was utilized as a precursor to produce some new interesting tetracyclic fused oxazolopyranoquinolinone analogues. The structures of the obtained quinolinone derivatives were confirmed using IR, LC-MS, ESI-MS and NMR techniques.

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“…The structure-activity relationship of the quinolones has been the subject of extensive reviews [4][5][6][7][8][9][10][11][12][13][14][15][16] . In our continuous effort to develop new chemotherapeutics with enhanced activities against resistant bacterial strains 17,18 , we introduced a new class of tricyclic compounds, namely thiadiazoloquinolones 19 . In our methodology, we took advantage of many known benzothiadiazoles ( Figure 2) with diverse biopharmaceutical activities [20][21][22][23][24][25][26] and we hybridized the thiadiazole moiety with the fluoroquinolone structure to introduce the new compound 9-cyclopropyl-4-fluoro-6-oxo-6,9-dihydro [1,2,5]thiadiazolo [3,4-h]quinoline carboxylic acid (16).…”

Section: Introductionmentioning

confidence: 99%

Design synthesis and antibacterial activity studies of new thiadiazoloquinolone compounds

Al‐Qawasmeh

Abadleh

Zahra

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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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 mg/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.

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Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents

Cited by 68 publications

References 38 publications

Structures and Antibacterial Properties of PLA-based Ciprofloxacin Composite Films Deposited by Low-Electron Beam Dispersion

Structures and Antibacterial Properties of PLA-based Ciprofloxacin Composite Films Deposited by Low-Electron Beam Dispersion

Synthesis of some novel oxazolopyranoquinolinones from 3-amino-4‐hydroxypyrano[3,2-c]quinolindione

Design synthesis and antibacterial activity studies of new thiadiazoloquinolone compounds

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