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Thematische Bibliographien / Alkyl-quinolones / Zeitschriftenartikel

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Zeitschriftenartikel zum Thema „Alkyl-quinolones“

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Veröffentlicht am 25. Mai 2024

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1

Liu, Huanhuan, Huadan Liu, Enhua Wang, et al. "Hydrogen Bond Assisted Three-Component Tandem Reactions to Access N-Alkyl-4-Quinolones." Molecules 28, no. 5 (2023): 2304. http://dx.doi.org/10.3390/molecules28052304.

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Hydrogen-bonding catalytic reactions have gained great interest. Herein, a hydrogen-bond-assisted three-component tandem reaction for the efficient synthesis of N-alkyl-4-quinolones is described. This novel strategy features the first proof of polyphosphate ester (PPE) as a dual hydrogen-bonding catalyst and the use of readily available starting materials for the preparation of N-alkyl-4-quinolones. The method provides a diversity of N-alkyl-4-quinolones in moderate to good yields. The compound 4h demonstrated good neuroprotective activity against N-methyl-ᴅ-aspartate (NMDA)-induced excitotoxicity in PC12 cells.

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2

Mollova-Sapundzhieva, Yordanka, Plamen Angelov, Danail Georgiev та Pavel Yanev. "Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors". Beilstein Journal of Organic Chemistry 19 (23 листопада 2023): 1804–10. http://dx.doi.org/10.3762/bjoc.19.132.

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β-Keto amides were used as convenient precursors to both 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides. The utility of this approach is demonstrated with the synthesis of fourteen novel and four known quinolone derivatives, including natural products of microbial origin such as HHQ and its C5-congener. Two compounds with high activity against S. aureus have been identified among the newly obtained quinolones, with MICs ≤ 3.12 and ≤ 6.25 µg/mL, respectively.

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3

Tang, Jing, and Xian Huang. "Convenient synthesis of 5-(Arylamino(Alkylthio)Methylene)-2,2-Dimethyl-1,3-Dioxane-4,6-Diones and 2-Arylthio-4-Quinolones." Journal of Chemical Research 2003, no. 3 (2003): 140–41. http://dx.doi.org/10.3184/030823403103173264.

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Meldrum's acid reacted with an aryl isothiocynate and alkyl halides to afford the 5-(arylamino(alkylthio)methylene)-5-methylthio-2,2-dimethyl-1,3-dioxane-4,6-diones and the compounds underwent thermal cyclization to give the 4-2-arylthio-4(1 H)-quinolones

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4

Bezuglyi, P. A., I. V. Ukrainets, V. I. Treskach, and A. V. Turov. "4-Hydroxy-2-quinolones. 1. Efficient method for obtaining 3-alkyl-4-hydroxy-2-quinolones." Chemistry of Heterocyclic Compounds 27, no. 11 (1991): 1237–38. http://dx.doi.org/10.1007/bf00471752.

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5

Saalim, Muhammad, Jessica Villegas-Moreno, and Benjamin R. Clark. "Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties." Molecules 25, no. 23 (2020): 5689. http://dx.doi.org/10.3390/molecules25235689.

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The alkyl-4-quinolones (AQs) are a class of metabolites produced primarily by members of the Pseudomonas and Burkholderia genera, consisting of a 4-quinolone core substituted by a range of pendant groups, most commonly at the C-2 position. The history of this class of compounds dates back to the 1940s, when a range of alkylquinolones with notable antibiotic properties were first isolated from Pseudomonas aeruginosa. More recently, it was discovered that an alkylquinolone derivative, the Pseudomonas Quinolone Signal (PQS) plays a key role in bacterial communication and quorum sensing in Pseudomonas aeruginosa. Many of the best-studied examples contain simple hydrocarbon side-chains, but more recent studies have revealed a wide range of structurally diverse examples from multiple bacterial genera, including those with aromatic, isoprenoid, or sulfur-containing side-chains. In addition to their well-known antimicrobial properties, alkylquinolones have been reported with antimalarial, antifungal, antialgal, and antioxidant properties. Here we review the structural diversity and biological activity of these intriguing metabolites.

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6

Vrla, Geoffrey D., Mark Esposito, Chen Zhang, Yibin Kang, Mohammad R. Seyedsayamdost, and Zemer Gitai. "Cytotoxic alkyl-quinolones mediate surface-induced virulence in Pseudomonas aeruginosa." PLOS Pathogens 16, no. 9 (2020): e1008867. http://dx.doi.org/10.1371/journal.ppat.1008867.

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7

BEZUGLYI, P. A., I. V. UKRAINETS, V. I. TRESKATCH, and A. V. TUROV. "ChemInform Abstract: 4-Hydroxy-2-quinolones. Part 1. Effective Preparation of 3-Alkyl-4- hydroxy-2-quinolones." ChemInform 24, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199337226.

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8

Chen, Bang-chi, Xian Huang, and Jin Wang. "A Versatile Synthesis of 2-Alkyl and 2-Aryl 4-Quinolones." Synthesis 1987, no. 05 (1987): 482–83. http://dx.doi.org/10.1055/s-1987-33427.

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9

Gupta, Rashmi, and Martin Schuster. "Quorum sensing modulates colony morphology through alkyl quinolones in Pseudomonas aeruginosa." BMC Microbiology 12, no. 1 (2012): 30. http://dx.doi.org/10.1186/1471-2180-12-30.

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10

Michalet, S., P. M. Allard, C. Commun, et al. "ePS6.03 Alkyl-Quinolones derivatives could predict Pseudomonas infection chronicity in cystic fibrosis." Journal of Cystic Fibrosis 19 (June 2020): S52—S53. http://dx.doi.org/10.1016/s1569-1993(20)30331-3.

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11

Al-Qawasmeh, Raed, Jalal Zahra, Monther Khanfar, Yusuf AL-Hiari, Mustafa El-Abadelah, and Wolfgang Voelter. "A Convenient Synthesis of 1-Alkyl-7-chloro-6-fluoro-3-nitro-4-quinolones." Letters in Organic Chemistry 6, no. 6 (2009): 511–14. http://dx.doi.org/10.2174/157017809789124812.

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12

Song, Yoon Ju, Jin Sun Choi, and Jae In Lee. "An Efficient Synthesis of 1-Alkyl-2-phenyl-4-quinolones from 2-Halobenzoic Acids." Bulletin of the Korean Chemical Society 34, no. 10 (2013): 3117–20. http://dx.doi.org/10.5012/bkcs.2013.34.10.3117.

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13

Dubern, Jean-Frédéric, and Stephen P. Diggle. "Quorum sensing by 2-alkyl-4-quinolones in Pseudomonas aeruginosa and other bacterial species." Molecular BioSystems 4, no. 9 (2008): 882. http://dx.doi.org/10.1039/b803796p.

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14

Niewerth, Heiko, Klaus Bergander, Siri Ram Chhabra, Paul Williams, and Susanne Fetzner. "Synthesis and biotransformation of 2-alkyl-4(1H)-quinolones by recombinant Pseudomonas putida KT2440." Applied Microbiology and Biotechnology 91, no. 5 (2011): 1399–408. http://dx.doi.org/10.1007/s00253-011-3378-0.

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15

Li, Dandan, Naoya Oku, Atsumi Hasada, Masafumi Shimizu, and Yasuhiro Igarashi. "Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp." Beilstein Journal of Organic Chemistry 14 (June 14, 2018): 1446–51. http://dx.doi.org/10.3762/bjoc.14.122.

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Exploration of rhizobacteria of the genus Burkholderia as an under-tapped resource of bioactive molecules resulted in the isolation of two new antimicrobial 2-alkyl-4-quinolones. (E)-2-(Hept-2-en-1-yl)quinolin-4(1H)-one (1) and (E)-2-(non-2-en-1-yl)quinolin-4(1H)-one (3) were isolated from the culture broth of strain MBAF1239 together with four known alkylquinolones (2 and 4–6), pyrrolnitrin (7), and BN-227 (8). The structures of 1 and 3 were unambiguously characterized using NMR spectroscopy and mass spectrometry. Compounds 1–8 inhibited the growth of the marine bacterium Tenacibaculum maritimum, an etiological agent of skin ulcers in marine fish, offering new opportunities to develop antibacterial drugs for fish farming.

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16

Ritzmann, Niklas H., Almuth Mährlein, Simon Ernst, Ulrich Hennecke, Steffen L. Drees, and Susanne Fetzner. "Bromination of alkyl quinolones by Microbulbifer sp. HZ11, a marine Gammaproteobacterium, modulates their antibacterial activity." Environmental Microbiology 21, no. 7 (2019): 2595–609. http://dx.doi.org/10.1111/1462-2920.14654.

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17

Ukrainets, I. V., S. G. Taran, O. A. Evtifeeva, et al. "4-Hydroxy-2-quinolones 19. A new synthesis of 3-Alkyl-2-oxo-4-hydroxyquinolines." Chemistry of Heterocyclic Compounds 30, no. 5 (1994): 591–95. http://dx.doi.org/10.1007/bf01169841.

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18

Sáenz, Fabián E., Alexis N. LaCrue, R. Matthew Cross, et al. "4-(1H)-Quinolones and 1,2,3,4-Tetrahydroacridin-9(10H)-Ones Prevent the Transmission of Plasmodium falciparum to Anopheles freeborni." Antimicrobial Agents and Chemotherapy 57, no. 12 (2013): 6187–95. http://dx.doi.org/10.1128/aac.00492-13.

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ABSTRACTMalaria kills approximately 1 million people a year, mainly in sub-Saharan Africa. Essential steps in the life cycle of the parasite are the development of gametocytes, as well as the formation of oocysts and sporozoites, in theAnophelesmosquito vector. Preventing transmission of malaria through the mosquito is necessary for the control of the disease; nevertheless, the vast majority of drugs in use act primarily against the blood stages. The study described herein focuses on the assessment of the transmission-blocking activities of potent antierythrocytic stage agents derived from the 4(1H)-quinolone scaffold. In particular, three 3-alkyl- or 3-phenyl-4(1H)-quinolones (P4Qs), one 7-(2-phenoxyethoxy)-4(1H)-quinolone (PEQ), and one 1,2,3,4-tetrahydroacridin-9(10H)-one (THA) were assessed for their transmission-blocking activity against the mosquito stages of the human malaria parasite (Plasmodium falciparum) and the rodent parasite (P. berghei). Results showed that all of the experimental compounds reduced or prevented the exflagellation of male gametocytes and, more importantly, prevented parasite transmission to the mosquito vector. Additionally, treatment with ICI 56,780 reduced the number of sporozoites that reached theAnophelessalivary glands. These findings suggest that 4(1H)-quinolones, which have activity against the blood stages, can also prevent the transmission ofPlasmodiumto the mosquito and, hence, are potentially important drug candidates to eradicate malaria.

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19

Barr, H., A. Fogarty, N. Halliday, et al. "P92 Systemic alkyl quinolones as novel biomarkers for pulmonary exacerbations in cystic fibrosis: a validation study." Thorax 71, Suppl 3 (2016): A133.2—A134. http://dx.doi.org/10.1136/thoraxjnl-2016-209333.235.

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20

Xu, Bin, Jun Shao, Xiaomei Huang, Xiaohu Hong, and Bingxin Liu. "Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation." Synthesis 44, no. 12 (2012): 1798–805. http://dx.doi.org/10.1055/s-0031-1290775.

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21

Li, Jianye, Weiwei Sun, Muhammad Saalim, Guixiang Wei, Diana A. Zaleta-Pinet, and Benjamin R. Clark. "Isolation of 2-Alkyl-4-quinolones with Unusual Side Chains from a Chinese Pseudomonas aeruginosa Isolate." Journal of Natural Products 83, no. 7 (2020): 2294–98. http://dx.doi.org/10.1021/acs.jnatprod.0c00026.

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22

Legendre, Claire, F. Jerry Reen, Marlies J. Mooij, Gerard P. McGlacken, Claire Adams та Fergal O'Gara. "Pseudomonas aeruginosa Alkyl Quinolones Repress Hypoxia-Inducible Factor 1 (HIF-1) Signaling through HIF-1α Degradation". Infection and Immunity 80, № 11 (2012): 3985–92. http://dx.doi.org/10.1128/iai.00554-12.

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ABSTRACTThe transcription factor hypoxia-inducible factor 1 (HIF-1) has recently emerged to be a crucial regulator of the immune response following pathogen perception, including the response to the important human pathogenPseudomonas aeruginosa. However, as mechanisms involved in HIF-1 activation by bacterial pathogens are not fully characterized, understanding how bacteria and bacterial compounds impact on HIF-1α stabilization remains a major challenge. In this context, we have focused on the effect of secreted factors ofP. aeruginosaon HIF-1 regulation. Surprisingly, we found thatP. aeruginosacell-free supernatant significantly repressed HIF-1α protein levels. Further characterization revealed that HIF-1α downregulation was dependent on a subset of key secreted factors involved inP. aeruginosapathogenesis, the 2-alkyl-4-quinolone (AQ) quorum sensing (QS) signaling molecules, and in particular the pseudomonas quinolone signal (PQS). Under hypoxic conditions, the AQ-dependent downregulation of HIF-1α was linked to the suppressed induction of the important HIF-1 target gene hexokinase II. Furthermore, we demonstrated that AQ molecules directly target HIF-1α protein degradation through the 26S-proteasome proteolytic pathway but independently of the prolyl hydroxylase domain (PHD). In conclusion, this is the first report showing that bacterial molecules can repress HIF-1α protein levels. Manipulation of HIF-1 signaling byP. aeruginosaAQs could have major consequences for the host response to infection and may facilitate the infective properties of this pathogen.

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23

Pistorius, Dominik, Angelika Ullrich, Simon Lucas, Rolf W. Hartmann, Uli Kazmaier, and Rolf Müller. "Biosynthesis of 2-Alkyl-4(1H)-Quinolones in Pseudomonas aeruginosa: Potential for Therapeutic Interference with Pathogenicity." ChemBioChem 12, no. 6 (2011): 850–53. http://dx.doi.org/10.1002/cbic.201100014.

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24

Shui, Hongling, Yuhong Zhong, Renshi Luo, et al. "Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities." Beilstein Journal of Organic Chemistry 18 (October 27, 2022): 1507–17. http://dx.doi.org/10.3762/bjoc.18.159.

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The acceptorless dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols and aryl/heteroaryl/alkyl secondary alcohols in one pot via a cyclometalated iridium-catalyzed ADC reaction. This method has some advantages, such as easy availability of raw materials, mild reaction conditions, wide range of substrates, and environmental friendliness which conforms to the principles of green chemistry. Furthermore, a gram-scale experiment with low catalyst loading offers the potential to access the aryl/heteroaryl quinolones in suitable amounts. In addition, the antibacterial and antifungal activities of the synthesized quinolines were evaluated in vitro, and the experimental results showed that the antibacterial activities of compounds 3ab, 3ad, and 3ah against Gram-positive bacteria and compound 3ck against C. albicans were better than the reference drug norfloxacin.

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25

Barr, Helen L., Nigel Halliday, David A. Barrett, et al. "Diagnostic and prognostic significance of systemic alkyl quinolones for P. aeruginosa in cystic fibrosis: A longitudinal study." Journal of Cystic Fibrosis 16, no. 2 (2017): 230–38. http://dx.doi.org/10.1016/j.jcf.2016.10.005.

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26

Song, Yoon Ju, Jin Sun Choi, and Jae In Lee. "ChemInform Abstract: An Efficient Synthesis of 1-Alkyl-2-phenyl-4-quinolones (VII) from 2-Halobenzoic Acids." ChemInform 45, no. 9 (2014): no. http://dx.doi.org/10.1002/chin.201409173.

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27

Wube, Abraham, Juan-David Guzman, Antje Hüfner, et al. "Synthesis and Antibacterial Evaluation of a New Series of N-Alkyl-2-alkynyl/(E)-alkenyl-4-(1H)-quinolones." Molecules 17, no. 7 (2012): 8217–40. http://dx.doi.org/10.3390/molecules17078217.

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28

Shao, Jun, Xiaomei Huang, Xiaohu Hong, Bingxin Liu, and Bin Xu. "ChemInform Abstract: Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation." ChemInform 43, no. 41 (2012): no. http://dx.doi.org/10.1002/chin.201241156.

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29

Rampioni, Giordano, Marilena Falcone, Stephan Heeb, et al. "Unravelling the Genome-Wide Contributions of Specific 2-Alkyl-4-Quinolones and PqsE to Quorum Sensing in Pseudomonas aeruginosa." PLOS Pathogens 12, no. 11 (2016): e1006029. http://dx.doi.org/10.1371/journal.ppat.1006029.

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30

Lin, San San, Stefan Kerscher, Ahmad Saleh, Ulrich Brandt, Uwe Groß, and Wolfgang Bohne. "The Toxoplasma gondii type-II NADH dehydrogenase TgNDH2-I is inhibited by 1-hydroxy-2-alkyl-4(1H)quinolones." Biochimica et Biophysica Acta (BBA) - Bioenergetics 1777, no. 11 (2008): 1455–62. http://dx.doi.org/10.1016/j.bbabio.2008.08.006.

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31

Barr, H. L., N. Halliday, D. A. Barrett, et al. "Diagnostic and prognostic significance of systemic alkyl quinolones for P. aeruginosa in cystic fibrosis: A longitudinal study; response to comments." Journal of Cystic Fibrosis 16, no. 6 (2017): e21. http://dx.doi.org/10.1016/j.jcf.2017.09.008.

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32

Ayubi, Erfan, Jamal Hallajzadeh, and Saeid Safiri. "Comment on data sparsity - Diagnostic and prognostic significance of systemic alkyl quinolones for P. aeruginosa in cystic fibrosis: A longitudinal study." Journal of Cystic Fibrosis 16, no. 6 (2017): e19-e20. http://dx.doi.org/10.1016/j.jcf.2017.07.012.

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33

Ukrainets, L. V., O. V. Gorokhova, S. G. Taran, et al. "4-hydroxy-2-quinolones. 22.* Synthesis and biological properties of 1-alkyl(aryl)-2-oxo-3-carbethoxy-4-hydroxyquinolines and their derivatives." Chemistry of Heterocyclic Compounds 30, no. 7 (1994): 829–36. http://dx.doi.org/10.1007/bf01169641.

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34

Seppänen, Otto, Mikko Muuronen, and Juho Helaja. "Gold-Catalyzed Conversion of Aryl- and Alkyl-Substituted 1-(o-Aminophenyl)-2-propyn-1-ones to the Corresponding 2-Substituted 4-Quinolones." European Journal of Organic Chemistry 2014, no. 19 (2014): 4044–52. http://dx.doi.org/10.1002/ejoc.201402224.

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35

Kilani-Feki, Olfa, Gérald Culioli, Annick Ortalo-Magné, Nabil Zouari, Yves Blache, and Samir Jaoua. "Environmental Burkholderia cepacia Strain Cs5 Acting by Two Analogous Alkyl-Quinolones and a Didecyl-Phthalate Against a Broad Spectrum of Phytopathogens Fungi." Current Microbiology 62, no. 5 (2011): 1490–95. http://dx.doi.org/10.1007/s00284-011-9892-6.

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36

Sciscenko, Iván, Paula García-Negueroles, Ana María Amat, et al. "Use of Fluorescence Spectroscopy and Chemometrics to Visualise Fluoroquinolones Photodegradation Major Trends: A Confirmation Study with Mass Spectrometry." Molecules 28, no. 2 (2023): 777. http://dx.doi.org/10.3390/molecules28020777.

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In this work, we employed EEM-PARAFAC (fluorescence excitation-emission matrices-parallel factor analysis) as a low-cost tool to study the oxidation pathways of (fluoro)quinolones. Amounts of 12.5 μM of enrofloxacin (ENR), ciprofloxacin (CIP), ofloxacin (OFL), oxolinic acid (OA), and flumequine (FLU), as individual solutions, were irradiated under UVA light. A 5-component PARAFAC model was obtained, four of them related to the parent pollutants, named as ENR-like (including CIP), OFL-like, OA-like, and FLU-like, and an additional one related to photoproducts, called ENRox-like (with an emission red-shift with respect to the ENR-like component). Mass spectrometry was employed to correlate the five PARAFAC components with their plausible molecular structures. Results indicated that photoproducts presenting: (i) hydroxylation or alkyl cleavages exhibited fingerprints analogous to those of the parent pollutants; (ii) defluorination and hydroxylation emitted within the ENRox-like region; iii) the aforementioned changes plus piperazine ring cleavage emitted within the OA-like region. Afterwards, the five antibiotics were mixed in a single solution (each at a concentration of 0.25 μM) in seawater, PARAFAC being also able to deconvolute the fingerprint of humic-like substances. This approach could be a potential game changer in the analysis of (fluorescent) contaminants of emerging concern removals in complex matrices, giving rapid visual insights into the degradation pathways.

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37

Ukrainets, I. V., N. L. Bereznyakova, V. A. Parshikov, and O. V. Gorokhova. "4-Hydroxy-2-quinolones 150*. Efficient synthesis, structure, and biological activities of 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkyl amides." Chemistry of Heterocyclic Compounds 44, no. 12 (2008): 1493–99. http://dx.doi.org/10.1007/s10593-009-0209-7.

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38

Dow, Lachlan. "How Do Quorum-Sensing Signals Mediate Algae–Bacteria Interactions?" Microorganisms 9, no. 7 (2021): 1391. http://dx.doi.org/10.3390/microorganisms9071391.

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Quorum sensing (QS) describes a process by which bacteria can sense the local cell density of their own species, thus enabling them to coordinate gene expression and physiological processes on a community-wide scale. Small molecules called autoinducers or QS signals, which act as intraspecies signals, mediate quorum sensing. As our knowledge of QS has progressed, so too has our understanding of the structural diversity of QS signals, along with the diversity of bacteria conducting QS and the range of ecosystems in which QS takes place. It is now also clear that QS signals are more than just intraspecies signals. QS signals mediate interactions between species of prokaryotes, and between prokaryotes and eukaryotes. In recent years, our understanding of QS signals as mediators of algae–bacteria interactions has advanced such that we are beginning to develop a mechanistic understanding of their effects. This review will summarize the recent efforts to understand how different classes of QS signals contribute to the interactions between planktonic microalgae and bacteria in our oceans, primarily N-acyl-homoserine lactones, their degradation products of tetramic acids, and 2-alkyl-4-quinolones. In particular, this review will discuss the ways in which QS signals alter microalgae growth and metabolism, namely as direct effectors of photosynthesis, regulators of the cell cycle, and as modulators of other algicidal mechanisms. Furthermore, the contribution of QS signals to nutrient acquisition is discussed, and finally, how microalgae can modulate these small molecules to dampen their effects.

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39

Seppaenen, Otto, Mikko Muuronen, and Juho Helaja. "ChemInform Abstract: Gold-Catalyzed Conversion of Aryl- and Alkyl-Substituted 1-(o-Aminophenyl)-2-propyn-1-ones to the Corresponding 2-Substituted 4-Quinolones." ChemInform 46, no. 8 (2015): no. http://dx.doi.org/10.1002/chin.201508224.

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40

Ukrainets, I. V., N. L. Bereznyakova, A. A. Davidenko, and S. V. Slobodzian. "4-Hydroxy-2-quinolones. 167*. Study of the reaction of ethyl 1-alkyl-substituted 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylates with phosphorus oxychloride." Chemistry of Heterocyclic Compounds 45, no. 8 (2009): 952–56. http://dx.doi.org/10.1007/s10593-009-0367-7.

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41

Depke, Tobias, Janne Gesine Thöming, Adrian Kordes, Susanne Häussler, and Mark Brönstrup. "Untargeted LC-MS Metabolomics Differentiates Between Virulent and Avirulent Clinical Strains of Pseudomonas aeruginosa." Biomolecules 10, no. 7 (2020): 1041. http://dx.doi.org/10.3390/biom10071041.

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Pseudomonas aeruginosa is a facultative pathogen that can cause, inter alia, acute or chronic pneumonia in predisposed individuals. The gram-negative bacterium displays considerable genomic and phenotypic diversity that is also shaped by small molecule secondary metabolites. The discrimination of virulence phenotypes is highly relevant to the diagnosis and prognosis of P. aeruginosa infections. In order to discover small molecule metabolites that distinguish different virulence phenotypes of P. aeruginosa, 35 clinical strains were cultivated under standard conditions, characterized in terms of virulence and biofilm phenotype, and their metabolomes were investigated by untargeted liquid chromatography—mass spectrometry. The data was both mined for individual candidate markers as well as used to construct statistical models to infer the virulence phenotype from metabolomics data. We found that clinical strains that differed in their virulence and biofilm phenotype also had pronounced divergence in their metabolomes, as underlined by 332 features that were significantly differentially abundant with fold changes greater than 1.5 in both directions. Important virulence-associated secondary metabolites like rhamnolipids, alkyl quinolones or phenazines were found to be strongly upregulated in virulent strains. In contrast, we observed little change in primary metabolism. A hitherto novel cationic metabolite with a sum formula of C12H15N2 could be identified as a candidate biomarker. A random forest model was able to classify strains according to their virulence and biofilm phenotype with an area under the Receiver Operation Characteristics curve of 0.84. These findings demonstrate that untargeted metabolomics is a valuable tool to characterize P. aeruginosa virulence, and to explore interrelations between clinically important phenotypic traits and the bacterial metabolome.

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Singh, Shweta, Sharanya Nerella, Srihari Pabbaraja, and Goverdhan Mehta. "Access to 2-Alkyl/Aryl-4-(1H)-Quinolones via Orthogonal “NH3” Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F." Organic Letters 22, no. 4 (2020): 1575–79. http://dx.doi.org/10.1021/acs.orglett.0c00172.

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Ukrainets, I. V., I. A. Tugaibei, N. L. Bereznyakova, V. N. Kravchenko, and A. V. Turov. "4-Hydroxy-2-quinolones 144. Alkyl-, arylalkyl-, and arylamides of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and their diuretic properties." Chemistry of Heterocyclic Compounds 44, no. 5 (2008): 565–75. http://dx.doi.org/10.1007/s10593-008-0076-7.

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UKRAINETS, I. V., O. V. GOROKHOVA, S. G. TARAN, et al. "ChemInform Abstract: 4-Hydroxy-2-quinolones. Part 22. Synthesis and Biological Properties of 1-Alkyl(aryl)-2-oxo-3-carboethoxy-4-hydroxy-quinolines and Their Derivatives." ChemInform 26, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199518153.

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Nguyen, Angela T., Jace W. Jones, Max A. Ruge, Maureen A. Kane, and Amanda G. Oglesby-Sherrouse. "Iron Depletion Enhances Production of Antimicrobials by Pseudomonas aeruginosa." Journal of Bacteriology 197, no. 14 (2015): 2265–75. http://dx.doi.org/10.1128/jb.00072-15.

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ABSTRACTCystic fibrosis (CF) is a heritable disease characterized by chronic, polymicrobial lung infections. WhileStaphylococcus aureusis the dominant lung pathogen in young CF patients,Pseudomonas aeruginosabecomes predominant by adulthood.P. aeruginosaproduces a variety of antimicrobials that likely contribute to this shift in microbial populations. In particular, secretion of 2-alkyl-4(1H)-quinolones (AQs) contributes to lysis ofS. aureusin coculture, providing an iron source toP. aeruginosabothin vitroandin vivo. We previously showed that production of one such AQ, thePseudomonasquinolone signal (PQS), is enhanced by iron depletion and that this induction is dependent upon the iron-responsive PrrF small RNAs (sRNAs). Here, we demonstrate that antimicrobial activity againstS. aureusduring coculture is also enhanced by iron depletion, and we provide evidence that multiple AQs contribute to this activity. Strikingly, aP. aeruginosaΔprrFmutant, which produces very little PQS in monoculture, was capable of mediating iron-regulated growth suppression ofS. aureus. We show that the presence ofS. aureussuppresses the ΔprrF1,2mutant's defect in iron-regulated PQS production, indicating that a PrrF-independent iron regulatory pathway mediates AQ production in coculture. We further demonstrate that iron-regulated antimicrobial production is conserved in multipleP. aeruginosastrains, including clinical isolates from CF patients. These results demonstrate that iron plays a central role in modulating interactions ofP. aeruginosawithS. aureus. Moreover, our studies suggest that established iron regulatory pathways of these pathogens are significantly altered during polymicrobial infections.IMPORTANCEChronic polymicrobial infections involvingPseudomonas aeruginosaandStaphylococcus aureusare a significant cause of morbidity and mortality, as the interplay between these two organisms exacerbates infection. This is in part due to enhanced production of antimicrobial metabolites byP. aeruginosawhen these two species are cocultured. Using both established and newly developed coculture techniques, this report demonstrates that iron depletion increasesP. aeruginosa's ability to suppress growth ofS. aureus. These findings present a novel role for iron in modulating microbial interaction and provide the basis for understanding how essential nutrients drive polymicrobial infections.

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Brewer, Luke K., Jace W. Jones, Catherine B. Blackwood, Mariette Barbier, Amanda Oglesby-Sherrouse, and Maureen A. Kane. "Development and bioanalytical method validation of an LC-MS/MS assay for simultaneous quantitation of 2-alkyl-4(1H)-quinolones for application in bacterial cell culture and lung tissue." Analytical and Bioanalytical Chemistry 412, no. 7 (2020): 1521–34. http://dx.doi.org/10.1007/s00216-019-02374-0.

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Ukrainets, I. V., L. V. Sidorenko, A. A. Davidenko, and A. K. Yarosh. "4-Hydroxy-2-quinolones. 174.* Hydrochlorides of [(alkylamino)alkyl]amides of 1-allyl- 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydro- quinoline-3-carboxylic acid – a new class of opioid receptor antagonists." Chemistry of Heterocyclic Compounds 46, no. 4 (2010): 445–51. http://dx.doi.org/10.1007/s10593-010-0529-7.

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Ukrainets, I. V., L. V. Sidorenko, A. A. Davidenko, and A. K. Yarosh. "ChemInform Abstract: 4-Hydroxy-2-quinolones. Part 174. Hydrochlorides of [(Alkylamino)alkyl]amides of 1-Allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid - A New Class of Opiod Receptor Antagonists." ChemInform 42, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.201104152.

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Huang, Bin, Yaqiu Long, Li-Rui Song, He Li, Shen-Feng Wang, and Jian-Ping Lin. "Metal-free Hypervalent Iodine-promoted Tandem Carbonyl Migration and Unactivated C(Ph)-C(Alkyl) Bond Cleavage for Quinolone Scaffold Synthesis." Chemical Communications, 2022. http://dx.doi.org/10.1039/d2cc02245a.

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An unexpected iodine(III)-mediated C(sp3)-C(sp2) bond cleavage of 3-(methylamino)-2-(2-substitutedbenzoyl)acrylates for efficient synthesis of privileged scaffold 4-quinolones was described. Notably, a wide range of alkyl groups (e.g. methyl, tert-butyl or alkyl chain)...

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Park, Cheol-Min, Jaehee Bae, and Jiyoung Chae. "Synthesis of 2‐Quinolones based on Visible Light‐Catalyzed Annulation of Diazo compounds." Advanced Synthesis & Catalysis, February 7, 2024. http://dx.doi.org/10.1002/adsc.202301220.

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Herein, we report a photocatalytic method for the synthesis of 2‐quinolones under mild conditions by employing α‐diazo acetamide as substrates. The use of Eosin Y as a photocatalyst allows an economical and environmentally benign synthetic method. The process involves the generation of radicals from diazo compounds promoted by a visible‐light‐induced proton‐coupled electron transfer (PCET) mechanism. The method demonstrates a broad substrate scope to provide various aryl‐ and alkyl‐substituted 2‐quinolones. To support the proposed mechanism, a series of mechanistic experiments were conducted.

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