Synthesis and antimicrobial activities of 2-azetidinyl-4-quinazolinone derivatives of diclofenac analogue

Patel, Navin B.; Patel, Jaymin C.

doi:10.1007/s00044-010-9345-y

Cited by 13 publications

(4 citation statements)

References 32 publications

(27 reference statements)

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“…These medicinal molecules have antibacterial and antifungal activities and some of them are even active against drug resistant Mycobacterium tuberculosis strains. However there is a need to test these novel quinolones in mammals for their potential toxicity [30,31,32,33,34,35,36]. Komarnicka et al made phosphine derivatives of sparfloxacin in high yield by treating sparfloxacin with methoxy(diphenyl)phosphine.…”

Section: Recent Developments In the Synthesis Of Quinolonesmentioning

confidence: 99%

The Current Case of Quinolones: Synthetic Approaches and Antibacterial Activity

et al. 2016

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Quinolones are broad-spectrum synthetic antibacterial drugs first obtained during the synthesis of chloroquine. Nalidixic acid, the prototype of quinolones, first became available for clinical consumption in 1962 and was used mainly for urinary tract infections caused by Escherichia coli and other pathogenic Gram-negative bacteria. Recently, significant work has been carried out to synthesize novel quinolone analogues with enhanced activity and potential usage for the treatment of different bacterial diseases. These novel analogues are made by substitution at different sites-the variation at the C-6 and C-8 positions gives more effective drugs. Substitution of a fluorine atom at the C-6 position produces fluroquinolones, which account for a large proportion of the quinolones in clinical use. Among others, substitution of piperazine or methylpiperazine, pyrrolidinyl and piperidinyl rings also yields effective analogues. A total of twenty six analogues are reported in this review. The targets of quinolones are two bacterial enzymes of the class II topoisomerase family, namely gyrase and topoisomerase IV. Quinolones increase the concentration of drug-enzyme-DNA cleavage complexes and convert them into cellular toxins; as a result they are bactericidal. High bioavailability, relative low toxicity and favorable pharmacokinetics have resulted in the clinical success of fluoroquinolones and quinolones. Due to these superior properties, quinolones have been extensively utilized and this increased usage has resulted in some quinolone-resistant bacterial strains. Bacteria become resistant to quinolones by three mechanisms: (1) mutation in the target site (gyrase and/or topoisomerase IV) of quinolones; (2) plasmid-mediated resistance; and (3) chromosome-mediated quinolone resistance. In plasmid-mediated resistance, the efflux of quinolones is increased along with a decrease in the interaction of the drug with gyrase (topoisomerase IV). In the case of chromosome-mediated quinolone resistance, there is a decrease in the influx of the drug into the cell.

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Section: Recent Developments In the Synthesis Of Quinolonesmentioning

confidence: 99%

The Current Case of Quinolones: Synthetic Approaches and Antibacterial Activity

et al. 2016

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“…136 It has been noted that Ding's protocol guarantees high atom efficiency, mild reaction conditions, ready availability of starting materials and yield of up to 90%. 89,133 Several bioactive natural products contain quinazolinone moieties, which have promising biological properties such as antibacterial, 137 antileishmanial, 138 anti-HIV, 139 anti-inammatory, 140 and antifungal 141 activities. Balalaie and co-workers successfully synthesized pseudo-peptides containing a quinazolinone moiety via U-4CR 142 using 3-amino-1,2,3,4-tetrahydro-4-oxoquinazoline-2-carboxylic acid derivatives 298.…”

Section: Synthesis Of Fused Six-membered Heterocyclic Compoundsmentioning

confidence: 99%

Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications

2020

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“…The drug was reported to be highly bactericidal and exerts its action by inhibiting the DNA synthesis of bacteria . Likewise, several small molecules bearing the 2‐[(2,6‐dichlorophenyl)amino]benzyl unit were shown to possess antibacterial potential .…”

Section: Introductionmentioning

confidence: 99%

Diclofenac‐Based Hydrazones and Spirothiazolidinones: Synthesis, Characterization, and Antimicrobial Properties

Kocabalkanli

Cihan-Üstündağ

Naesens

et al. 2017

Archiv der Pharmazie

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We report here the synthesis, structural characterization, and biological evaluation of novel diclofenac-based hydrazone (4a-f) and spirothiazolidinone (5a-f, 6a-f) derivatives designed as potential antimicrobial agents. The compounds were evaluated in vitro for their antiviral activity against a wide spectrum of DNA and RNA viruses. They were further screened in vitro against different strains of bacteria and fungi. The hydrazone derivatives, 4a and 4c-f, were found to be active against herpesviruses (HSV-1, HSV-2, and HSV-1 TK ), vaccinia virus, and Coxsackie B4 virus, with EC values between 6.6 µg/mL and 14.7 μg/mL, and the selectivity index values were greater than 10 for 4a and 4f. The newly synthesized compounds (4-6) were inactive against the bacterial and the fungal strains tested, at levels below 2500, 1250, or 625 μg/mL. Interestingly, the key intermediate 3 with a free hydrazide moiety displayed antifungal properties against Candida albicans and C. parapsilosis at MIC values of 4.88 µg/mL and 78.12 μg/mL, respectively.

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Synthesis and antimicrobial activities of 2-azetidinyl-4-quinazolinone derivatives of diclofenac analogue

Cited by 13 publications

References 32 publications

The Current Case of Quinolones: Synthetic Approaches and Antibacterial Activity

The Current Case of Quinolones: Synthetic Approaches and Antibacterial Activity

Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications

Diclofenac‐Based Hydrazones and Spirothiazolidinones: Synthesis, Characterization, and Antimicrobial Properties

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