• YAKHAK HOEJI
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• v.52 no.6
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• pp.514-519
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• 2008

We developed a convenient synthetic route to 3-alkylated 2-phenyl-4-quinolone derivatives (4a-h and 5a-c), which were expected to retain antitumor activity. A series of 2,3-dihydro-2-hydroxy-2-phenyl-4-quinolones (3a-h) was synthesized through dehydration, dealcoholation and hydration using acid-catalyzed one-pot reaction from anilines and ethyl benzoylacetates. 3-Methyl (or 3,3-dimethyl)-2-phenyl-4-quinolone derivatives 4 and 5 were synthesized from 3a-h through the methylation using methyl iodide. Formation of quinolone nucleus was undertaken with p-toluenesulfonic acid (p-TSA) at $90{\sim}110^{\circ}C$ in toluene for 3${\sim}$7.5 hr over the Dean-Stark apparatus. The key intermediates in these preparations are ${\beta}$-ketoesters 2a-h, which can be readily obtained from the corresponding anilines 1a-e by reaction with ethyl bezoylacetates.

• Archives of Pharmacal Research
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• v.21 no.4
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• pp.445-451
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• 1998

A series of 5-hydroxy-4-quinolone (3) and 5-methoxy-4-quinolone (4) derivatives were synthesized as truncated acridone analogues and evaluated for antitumor, antiheroes and antituberculosis activities. Among them 5-hydroxy-8-methoxy-quinolone showed potent antitumor activity ($IC_{50}$=17.7 $\mu\textrm{M}$ for HL60) which was greater than that of acronycine. However, these compounds didn't show any significant antiheroes or antituberculosis activity.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.232.1-232.1
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• 2002

Methods of 14C-radio isotope labeling of quinolone intermediates at four different sites are described. 14C-radio isotope labeled quinolone intermediates can be synthesized from 14C-1-malonic acid, 14C-2-malonic acid, 14C-benzene ring. and 14C-trimethyl orthoformate. The major site of 14C-radio isotope labeled quinolone intermediates is from 14C-2-malonic acid. We want to help customers to choose the best way for synthesis of 14C-radio isotope labeled quinolone derivatives. and give a general comprehension for 14C-radio isotope labeled pharmaceutical compounds. (omitted)

• Bulletin of the Korean Chemical Society
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• v.31 no.1
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• pp.64-68
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• 2010

Four quinolone alkaloids were isolated by bioactivity-guided fractionation from the methanol extracts of Evodiae fructus fruits. Structures of compounds were elucidated by spectroscopic analysis ($^1H$-, $^{13}$C-NMR and MS), as follows: 1-methyl-2-undecyl-4(1H)-quinolone (1), evocarpine (2), dihydroevocarpine (3) and mixture of [1-methyl-2-[(Z)-10-pentadecenyl]-4(1H)-quinolone and 1-methyl-2-[(Z)-6-pentadecenyl]-4(1H)-quinolone] (4). They inhibited the interaction of sICAM-1 and LFA-1 in THP-1 cells at $IC_{50}$ values of >150 (1), 109.8 (2), >150 (3) and $40.9 {\mu}M$ (4), respectively,

• Journal of Life Science
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• v.20 no.6
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• pp.964-967
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• 2010

Plasmid-mediated quinolone resistance (PMQR) determinants have been contributed to quinolone resistance of gram-negative bacteria worldwide. However, little data on the prevalence of these determinants in bacteria from animals are available in Korea. In this study, the prevalence of PMQR genes was investigated with E. coli originating from diseased animals. Among 55 E. coli tested, 11 showed PMQR genes by PCR. The most prevalent genotype was qepA (14.5%), followed by aac(6')-Ib-cr (7.3%) and qnrS (1.8%). Interestingly, two isolates with PMQR genes did not show quinolone resistance in this study. The isolates exhibited higher fluoroquinolone resistance in aac(6')-Ib-cr in combination with qnrS or qepA compared with aac(6')-Ib-cr only. In a conjugal transfer test, PMQR genes were transferred from donor to recipient.

• YAKHAK HOEJI
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• v.54 no.4
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• pp.288-294
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• 2010

Three dimensional quantitative-structure relationships (3D-QSARs) models between structures of phenoxy, phenylthio or benzyloxy substituted quinolone analogues and their antitrypanosomal activity against Chagas disease (Trypanosoma cruzi) were derived and discussed quantitatively using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) methods. The optimized CoMFA 1 model ($q^2$=0.528 and $r^2$=0.964) showed the best statistical results. According to the optimized CoMFA 1 model, the antitrypanosomal activities were dependent on the steric (60.0%) and electrostatic (36.2%) factors of quinolone derivatives. From the contour maps, it is predicted that the activity will be increased when sterically favored groups were located in $R_4$ and $R_5$ position and sterically disfavored groups were located in $R_2$ position. Also, the positively charged groups on $R_2$ would be able to increase the antitrypanosomal activities.

• YAKHAK HOEJI
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• v.60 no.1
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• pp.1-7
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• 2016

The aim of this study was to investigate the prevalence of quinolone resistant E. coli from retail meat and to characterize the resistant determinants. Determination of minimum inhibitory concentration, the sequence analysis of gyrA, gyrB, parC, and parE quinolone resistance determining regions (QRDR), the presences of plasmid mediated quinolone resistance (PMQR) and the expression of efflux pump genes were investigated. Of the total 277 retail meat samples, 67 coli form bacteria were isolated. 15 of 67 isolates showed nalidixic acid resistance and 7 of 15 nalidixic acid resistant isolates were also resistant to ciprofloxacin, moxifloxacin and levofloxacin. 11 of 15 nalidixic acid resistant strains were isolated from chicken, 2 of 15 were isolated from beef and 2 of 15 were isolated from pork samples. 11 of 15 nalidixic acid resistant strains have single mutation at codon 87 (D87N or D87G) in gyrA, 2 of 11 gyrA mutants have double mutations at codon 86 and 87 (L86A and L87I) in parC with mutations at codon 434+445+465 or 429 in gyrB. 2 of 15 resistant isolates harbored qnrS, a PMQR determinant. Over expression of the acrB gene, efflux pump gene (3.93~16.53 fold), was observed in 10 of 15 resistant isolates.

• Bulletin of the Korean Chemical Society
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• v.30 no.5
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• pp.1031-1034
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• 2009

Fluorescence of quinolones including norfloxacin, ciprofloxacin and S- and R-ofloxacin is quenched upon association with single and double-stranded DNA (ss- and ds-DNA). The ratios of fluorescence intensity in the presence of DNA to its absent were plotted with respect to the DNA concentration to construct the Stern-Volmer plot. The slope of the Stern-Volmer plot become larger as the temperature is lowered, ensuring that the fluorescence quenching is static process, i.e., the fluorescence is quenched by formation of the non-fluorescent complex between quinolone and DNA. In the static quenching mechanism, the quenching constant which is equivalent to the slope of the Stern-Volmer plot, is considered as the equilibrium constant for the association of quinolones and DNA. From the temperature-dependent equilibrium constant, ${\Delta}H^0\;and\;{\Delta}S^0$ was obtained using the van’t Hoff relation. In general, association of the quinolone with ds- as well as ss-DNA is energetically favorable (an exothermic) process while the entropy change was unfavorable. Due to the steric effect of the substituents, the effect of the quinolone ring is smaller on the ss-DNA compared to ds-DNA.

• Applied Biological Chemistry
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• v.41 no.7
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• pp.550-555
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• 1998

For fluoro-quinolone carboxylic acid derivatives, one bond carbon-fluorine coupling constants are ranged from 249 Hz to 257 Hz regardless of positions. But geminal and vicinal carbon-fluorine coupling constants vary according to positions, namely, geminal coupling constants are ranged from 6 Hz to 23 Hz, and vicinal coupling constants are ranged from 1.9 Hz to 7 Hz. In cases of proton-fluorine couplings, three bond coupling constants are ranged from 9 Hz to 10.3 Hz, and four bond coupling constants ate ranged from 6 Hz to 8.3 Hz.

• Journal of Korean Foot and Ankle Society
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• v.27 no.3
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• pp.103-107
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• 2023

Quinolone antibiotics are frequently prescribed for suspected respiratory or urinary tract infections because of their effectiveness and generally perceived safety profile. On the other hand, some studies have raised concerns regarding the potential association between quinolone use and Achilles tendinopathy or tendon rupture. There is a lack of reports on the link between quinolone use and multiple tendon and tendon attachment site pain in the foot and ankle joints; hence, this study examined this issue further. This paper presents a case report of a patient with persistent Achilles tendinopathy and multiple tendon and tendon attachment site pain in the foot who did not respond adequately to conservative treatments. In particular, the discontinuation of quinolone use resulted in favorable clinical outcomes. This report offers valuable insights into the potential risks associated with quinolone antibiotics and highlights the importance of vigilance when managing patients with tendon-related complaints. A comprehensive review of the relevant literature is also presented to contextualize these findings.