Synthesis and in vitro microbial activities of amides of pyridoquinolone

Patel, Navin B.; Patel, Sarvil D.; Chauhan, H. I.

doi:10.1007/s00044-010-9443-x

Cited by 9 publications

(5 citation statements)

References 16 publications

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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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“…4-Amino-3-(2-methylbenzyl)coumarin derivatives [13] exhibited potent estrogenic activity on the estrogen receptor positive (ER þ ) human MCF-7 breast cancer cell line. 4-Hydroxy coumarin derivatives [14] showed pronounced prolongation of prothrombin time with anticoagulant values similar to that of warfarin. Benzothiazolyl coumarin acetamide derivatives [15] exhibited strong in vitro anti-HIV effect against the wild-type HIV-1 cell line.…”

Section: Introductionmentioning

confidence: 89%

Microwave assisted synthesis of dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones

Puttaraju

Shivashankar

Chandra

et al. 2013

European Journal of Medicinal Chemistry

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Microwave assisted synthesis of dihydrobenzo [4,5]imidazo [1,2-a] pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo [4,5] In general, all the compounds possessed better antifungal properties than antibacterial properties. The coumarin substituted dihydrobenzo [4,5]imidazo[1,2-a]pyrimidin-4-one (4g) (R ¼ i-Pr, R 1 ¼ 6-Cl) was found to be the most potent cytotoxic compound (88%) against Dalton's Ascitic Lymphoma cell line at the concentration of 100 mg/mL.

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“…All amides/sulfonamides/thioureido amides-quinolone derivatives showed potent activity against P. aeruginosa and E. coli with MIC ranging from 0.17 to 0.80 μg/mL and more active than the reference CPFX (MIC: 1 μg/mL) [89]. The SAR study demonstrated that electronwithdrawing and electron-donating groups at phenyl ring were active, as evidenced by derivatives with -Cl and -OH that showed similar activity; variations in activities of amides were observed, and the order of amides contributed to the activity was amides > sulfonamides > thioureido amides.…”

Section: C-2 Modificationsmentioning

confidence: 98%

4‐Quinolone Derivatives and Their Activities Against Gram‐negative Pathogens

Jiang

2018

Journal of Heterocyclic Chem

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Gram‐negative pathogens represent a significant global health threat, while the emergency and widespread of drug resistance make the situation even worse. As “privileged building blocks,” 4‐quinolones including fluoroquinolones are mainstays of chemotherapy against various bacterial infections. However, as other antibiotics, the resistance of Gram‐negative bacteria to 4‐quinolones develops rapidly and spreads widely throughout the world. To overcome the resistance and improve the potency, a number of 4‐quinolone derivatives were designed, synthesized, and screened for their in vitro and in vivo activities against representative Gram‐negative pathogens. This review aims to summarize the recent advances made towards the discovery of 4‐quinolone derivatives as anti‐Gram‐negative agents as well as their structure–activity relationship. The enriched structure–activity relationship paves the way to the further rational development of 4‐quinolones with excellent potency against both drug‐susceptible and drug‐resistant Gram‐negative pathogens.

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Synthesis and in vitro microbial activities of amides of pyridoquinolone

Cited by 9 publications

References 16 publications

The Current Case of Quinolones: Synthetic Approaches and Antibacterial Activity

The Current Case of Quinolones: Synthetic Approaches and Antibacterial Activity

Microwave assisted synthesis of dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones

4‐Quinolone Derivatives and Their Activities Against Gram‐negative Pathogens

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