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Journal articles on the topic 'Quinoline carboxylic acid'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Öhlinger, Stefan Holger. "AN EFFICIENT SYNTHESIS OF β-(3-QUINOLINYL)-α-ALANINE". SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 17, № 17 (2009): 1–8. http://dx.doi.org/10.48141/sbjchem.v17.n17.209.4_2009.pdf.

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A convenient synthesis for β-(3-quinolinyl)-α-alanine (4) is presented. Condensation of 2-chloro-3-chloromethylquinoline (5) with diethyl acetamidomalonate (2) gave high yield of diethyl 2-acetylamino-2-(2-chloro-3-quinolinylmethyl)- propanedionate (6), which was dehalogenated in the presence of ammonium formate and palladium/charcoal. Diethyl 2-acetamido-2-(3-quinolinylmethyl)-malonate (3) was easily converted to the amino acid. The condensation reaction between 2 and 6 is also useful for the construction of (1H)-2,3-dihydropyrrolo[2,3-b]quinoline-2,2-bis(carboxylic acid) and pyrrolo[2,3-b]qu

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2

Gaber, Ahmed, Walaa F. Alsanie, Majid Alhomrani, Abdulhakeem S. Alamri, Ibrahim M. El-Deen, and Moamen S. Refat. "Synthesis and Characterization of Some New Coumarin Derivatives as Probable Breast Anticancer MCF-7 Drugs." Crystals 11, no. 5 (2021): 565. http://dx.doi.org/10.3390/cryst11050565.

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This study aimed to synthesize quinolinone derivatives and investigate their cytotoxic activity. The compound 1-azacoumarin-3-carboxylic acid (2-oxo-1H-quinoline-3-carboxylic acid) was obtained via the cyclocondensation of 2-hydroxybenzaldehyde with diethyl malonate in base catalyst to give ethyl coumarin-3-carboxylate, followed by the ammonolysis of ester (ethyl coumarin-3-carboxylate) with ammonia in the presence of anhydrous potassium carbonate. Treatment of 2-oxo-1H-quinoline-3-carboxylic acid with acetic anhydride, cinnamaldehyde, cinnamic acid and methyl 5-phenyl-2-cyano-2,4-pentadienoat

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3

Dobson, A. J., and R. E. Gerkin. "Quinoline-4-carboxylic Acid." Acta Crystallographica Section C Crystal Structure Communications 54, no. 12 (1998): 1883–85. http://dx.doi.org/10.1107/s0108270198009585.

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4

Yadav, Pradeep, and Y. C. Joshi. "Synthesis and Spectral Study of Novel Norfloxacin Derivatives." E-Journal of Chemistry 5, s2 (2008): 1154–58. http://dx.doi.org/10.1155/2008/357073.

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Reaction of [1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinolone-3-carboxylic acid (norfloxacin) with thiazole / benzothiazole diazonium chloride to get new piperazine substituted norfloxacin derivative. These norfloxacin derivatives were further condensed with variousβ-diketone to get novel acid derivatives of 1-Ethyl-6-fluoro-4-oxo-7- [4 (thiazol-2-yldiazenyl)-piperzin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid (6a-e) and 7-(4-(benzo[d]thiazol-2-yldiazenyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid (6 f-j). Structures of these compounds were

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5

Gauvreau, D., I. E. Swift, and M. J. Waring. "Studies on antibiotic biosynthesis by protoplasts and resting cells of Streptomyces echinatus. Part II. Effect of chromophore precursors." Canadian Journal of Microbiology 32, no. 5 (1986): 363–72. http://dx.doi.org/10.1139/m86-071.

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Washed cell and protoplast suspensions from Streptomyces echinatus A8331, which produces the quinoxaline antibiotic echinomycin, have been used to study the effects of analogues of the natural chromophore upon antibiotic biosynthesis. Addition of quinoline-2-carboxylic acid caused a decrease in the labelling of echinomycin from L-[methyl-14C]methionine and an increase in labelled chloroform-extractable material. Quinoxaline-2-carboxylic acid increased the incorporation of radioactivity into both fractions. Thieno[3,2-b]pyridine-5-carboxylic acid, 6-methylquinoline-2-carboxylic acid, and quinol

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6

Ng, Seik Weng. "(Quinoline-2-carboxylato-κO)(quinoline-2-carboxylic acid-κO)bis(quinoline-2-carboxylic acid-κ2N,O)potassium". Acta Crystallographica Section E Structure Reports Online 66, № 8 (2010): m948. http://dx.doi.org/10.1107/s1600536810027510.

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7

Abd El-Aal, Hassan A. K., and Talaat I. El-Emary. "Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence." Australian Journal of Chemistry 72, no. 12 (2019): 945. http://dx.doi.org/10.1071/ch19363.

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An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implicatio

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8

Abd El-Aal, Hassan A. K., and Talaat I. El-Emary. "Corrigendum to: Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence." Australian Journal of Chemistry 72, no. 12 (2019): 990. http://dx.doi.org/10.1071/ch19363_co.

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An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implicatio

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9

Zacharopoulos, Nikolaos, Gregor Schnakenburg, Eleni I. Panagopoulou, Nikolaos S. Thomaidis, and Athanassios I. Philippopoulos. "Pyridine–Quinoline and Biquinoline-Based Ruthenium p-Cymene Complexes as Efficient Catalysts for Transfer Hydrogenation Studies: Synthesis and Structural Characterization." Molecules 30, no. 14 (2025): 2945. https://doi.org/10.3390/molecules30142945.

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Searching for new and efficient transfer hydrogenation catalysts, a series of new organometallic ruthenium(II)-arene complexes of the formulae [Ru(η6-p-cymene)(L)Cl][PF6] (1–8) and [Ru(η6-p-cymene)(L)Cl][Ru(η6-p-cymene)Cl3] (9–11) were synthesized and fully characterized. These were prepared from the reaction of pyridine–quinoline and biquinoline-based ligands (L) with [Ru(η6-p-cymene)(μ-Cl)Cl]2, in 1:2 and 1:1, metal (M) to ligand (L) molar ratios. Characterization includes a combination of spectroscopic methods (FT-IR, UV-Vis, multi nuclear NMR), elemental analysis and single-crystal X-ray c

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10

Fang, Guiqian, Hao Wang, Zhancun Bian, et al. "2-(4-Boronophenyl)quinoline-4-carboxylic acid derivatives: Design and synthesis, aggregation-induced emission characteristics, and binding activity studies for D-ribose with long-wavelength emission." Journal of Chemical Research 44, no. 3-4 (2019): 152–60. http://dx.doi.org/10.1177/1747519819893642.

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Long-wavelength fluorescent sensors with large Stokes shifts show useful applications in chemical biology and clinical laboratory diagnosis. We have recently reported [4-(4-{[3-(4-boronobenzamido)propyl]carbamoyl}quinolin-2-yl)phenyl]boronic acid that can selectively recognize d-ribose in a buffer solution of pH 7.4. However, the short emission wavelength (395 nm) and aggregation-caused quenching effect are not conducive to applications as a sensor. Novel diboronic acid compounds are synthesized using 2-(4-boronophenyl)quinoline-4-carboxylic acid as the building block and p-phenylenediamine as

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11

Shabeeb, Ihsan, Luay Al-Essa, Majed Shtaiwi, et al. "New Hydrazide-hydrazone Derivatives of Quinoline 3-Carboxylic Acid Hydrazide: Synthesis, Theoretical Modeling and Antibacterial Evaluation." Letters in Organic Chemistry 16, no. 5 (2019): 430–36. http://dx.doi.org/10.2174/1570178616666181227122326.

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A series of biologically active 3-quinoline carboxylic acid hydrazide-hydrazones has been synthesized from 3-quinoline carboxylic acid hydrazide and a variety of aldehydes, with moderate to good yields. The chemical structures of the new products were confirmed by elemental analysis, IR, and 1H NMR, 13C NMR spectral data. The structural and frontier molecular orbital (FMO) properties and the density functional theory (DFT) calculations were conducted for the new compounds. The new hydrazide-hydrazones exhibited low to moderate antibacterial activity against Staphylococcus aureus and Esherichia

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12

Habashneh, Almeqdad Y., Mustafa M. El-Abadelah, Mohammad S. Mubarak, and Wolfgang Voelter. "Heterocycles [f]-Fused onto Quinolones. Synthesis of Novel Dioxo-Nethylpyrano[ 2,3-f ]- and [3,2-f ]quinoline-10-carboxylic Acids." Zeitschrift für Naturforschung B 68, no. 9 (2013): 1049–55. http://dx.doi.org/10.5560/znb.2013-3122.

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A model N-ethyl-1,10-dioxo-3-phenylpyrano[3,2- f ]quinoline-9-carboxylic acid (8) and the isomeric (2-substituted) pyrano[2,3- f ]quinoline-9-carboxylic acids (6 and 7) were prepared from the corresponding 6/7-aminochromen-4-ones via the Gould-Jacobs reaction. The new tricyclic heterocycles 6-8 exhibit moderate antibacterial activity (MIC=16 - 64 μgmL-1) against E. coli and S. aureus

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13

Fedorowicz, Joanna, Karol Gzella, Paulina Wiśniewska, and Jarosław Sączewski. "2,2′-((1,4-Dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene))bis(quinoline-3-carboxylic acid)." Molbank 2019, no. 4 (2019): M1093. http://dx.doi.org/10.3390/m1093.

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The title compound, 2,2′-((1,4-dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene))bis(quinoline-3-carboxylic acid) was synthesized from isoxazolo[3,4-b]quinolin-3(1H)-one and dimethyl acetylenedicarboxylate (DMAD) via a double aza-Michael addition followed by [1,3]-H shifts. The product was characterized by infrared and nuclear magnetic resonance spectroscopy, as well as elemental analysis and high-resolution mass spectrometry (HRMS). The proposed reaction mechanism was rationalized by density functional theory (DFT) calculations.

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14

Gao, Wentao, Guihai Lin, Yang Li, Xiyue Tao, Rui Liu, and Lianjie Sun. "An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives." Beilstein Journal of Organic Chemistry 8 (October 30, 2012): 1849–57. http://dx.doi.org/10.3762/bjoc.8.213.

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An efficient access to the tetracyclic-fused quinoline systems, 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives 4a–l, is described, involving the intramolecular Friedel–Crafts acylation reaction of 2-(phenoxymethyl)-4-phenylquinoline-3-carboxylic acid derivatives 3a–l aided by the treatment with PPA (polyphosphoric acid) or Eaton’s reagent. The required starting compound (2) was obtained by Friedländer reaction of 2-aminobenzophenone (1) with 4-chloroethylacetoacetate by using CAN (cerium ammonium nitrate, 10 mol %) as catalyst at room temperature. The substrates 3a–l were pre

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15

Li, Qian, Qitong Huang, Jie-Ji Zhu, Wen-Gang Ji, and Qing-Xiao Tong. "Carbon dots–quinoline derivative nanocomposite: facile synthesis and application as a “turn-off” fluorescent chemosensor for detection of Cu2+ ions in tap water." RSC Advances 6, no. 90 (2016): 87230–36. http://dx.doi.org/10.1039/c6ra21034a.

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In this paper, a novel quinoline derivative: 8-(pyridin-2-ylmethoxy)quinoline-2-carboxylic acid (Q) has been successfully synthesized, then it was coupled with carbon dots (CDs) to synthesize a CDs–Q nanocomposite by a simple and green method.

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16

Qin, Zengquan, Hilary A. Jenkins, Simon J. Coles, Kenneth W. Muir, and Richard J. Puddephatt. "Self-assembly of one-dimensional polymers by coordination and hydrogen bonding in palladium(II) complexes." Canadian Journal of Chemistry 77, no. 1 (1999): 155–57. http://dx.doi.org/10.1139/v99-027.

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The ligands L = pyridine- or quinoline-carboxylic acid easily give complexes trans-[PdCl2L2], which self-assemble through hydrogen bonding between carboxylic acid groups to give one-dimensional polymers, as proved by structure determinations when L = NC5H4COOH-4, NC5H4COOH-3, and 2-Ph-NC9H5COOH-4.Key words: polymer, hydrogen-bonding, palladium, coordination.

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17

Al-Qawasmeh, Raed A., Monther A. Khanfar, Musa H. Abu Zarga, and Murad A. AlDamen. "2-(4-Methylphenyl)quinoline-4-carboxylic acid." Acta Crystallographica Section E Structure Reports Online 68, no. 10 (2012): o2892. http://dx.doi.org/10.1107/s160053681203797x.

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18

Gurjar, Vinod Kumar. "Synthesis and ADMET Study of Some 1, 8-Naphthyidine and Quinoline 3-Carboxylic Acid Derivatives." International Journal for Research in Applied Science and Engineering Technology 9, no. 11 (2021): 1932–38. http://dx.doi.org/10.22214/ijraset.2021.39142.

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Abstract: The extremely drug resistant may be a worldwide public ill health in recent years. Molecules with newer targets and an alternate mechanism of action is an urgent requirement of improvement of latest drugs. The utilization of heterocyclic compounds has been increased dramatically over the last 70 years due to their wide selection of technical applications and their favorable environmental and toxicological properties The 1,8-naphthyridine and quinoline 3-carboxylic acid derivatives that we'll manufacture during this method will change the potency and specificity of fluoroquinolones. T

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19

Khan, Imtiaz, Syed Jawad Ali Shah, Syeda Abida Ejaz, et al. "Investigation of quinoline-4-carboxylic acid as a highly potent scaffold for the development of alkaline phosphatase inhibitors: synthesis, SAR analysis and molecular modelling studies." RSC Advances 5, no. 79 (2015): 64404–13. http://dx.doi.org/10.1039/c5ra12455g.

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20

Khidre, Rizk E., Tahah A. Ameen, and Mounir A. I. Salem. "Tetrazoloquinolines: Synthesis, Reactions, and Applications." Current Organic Chemistry 24, no. 4 (2020): 439–64. http://dx.doi.org/10.2174/1385272824666200217095341.

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This review summarizes the synthesis, reactions, and biological activities of tetrazolo[1,5-a]quinoline derivatives. These derivatives were synthesized by several methods such as i) from the reaction of 2-chloroquinoline with sodium azide ii) from diazotization 2-hydrazinylquinoline derivatives, and iii) from intramolecular cyclocondensation of 2-azidoarylidenes. Also, the chemical reactions and pharmacological activities of some tetrazoloquinolines such as tetrazolo[1,5-a]quinoline-4-carbaldehyde, 5-chlorotetrazolo[ 1,5-a]quinoline, 4-(chloromethyl)tetrazolo[1,5-a]quinoline, tetrazolo[1,5- a]

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21

Ishkov, Yurii V., Vira V. Veduta, Nadiia F. Fedko, and Natalia M. Bohdan. "A Simple Preparative Synthesis of Isomeric 2-Chloroquinolinecarboxylic Esters." Journal of Organic and Pharmaceutical Chemistry 21, no. 4 (2023): 11–17. http://dx.doi.org/10.24959/ophcj.23.298574.

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A simple two-stage method for the synthesis of isomeric esters of 2-chloroquinoline-5-, 6-, 7-carboxylic acids by successive oxidation and chlorination reactions of methyl quinoline-5-, 6-, 7-carboxylates has been developed. The target compounds have been obtained in acceptable yields using readily available reagents, simple transformations, and purification methods. Quinoline-8-carboxylic acid ester is unreactive under these conditions. The ester of 2-chloroquinoline-8-carboxylic acid has been obtained with an overall yield of 55%, starting from 8-methylquinoline. The multi-stage process is p

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22

Kochel, Andrzej, Małgorzata Hołyńska, Kamil Twaróg, Aneta Jezierska, Jarosław J. Panek, and Jacek Wojaczyński. "A new mixed-valence Cu^I/Cu^II three-dimensional coordination polymer constructed with an N,O-donor ligand generated via solvothermal synthesis: structural features and magnetic properties." Acta Crystallographica Section C Structural Chemistry 78, no. 7 (2022): 405–13. http://dx.doi.org/10.1107/s2053229622005812.

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A new mixed-valence CuI/CuII three-dimensional coordination polymer, poly[[diaquabis[μ4-2-(pyrazin-2-yl)quinoline-4-carboxylato]dicopper(I)copper(II)] bis(tetrafluoridoborate)], {[Cu3(C14H8N3O2)2(H2O)2](BF4)2} n , was synthesized and characterized, with 2-(pyrazin-2-yl)quinoline-4-carboxylic acid being employed as a linker ligand. The ligand was isolated as its hydrochloride salt, 4-carboxy-2-(pyrazin-2-yl)quinolin-1-ium chloride dihydrate, C14H10N3O2 +·Cl−·2H2O. The compounds show luminescence at 550 nm for the ligand and at 565 nm for the polymer at 297 K. The ligand structure was rationaliz

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23

Michalke, R., K. Taraz, and H. Budzikiewiez. "Azoverdin -an Isopyoverdin." Zeitschrift für Naturforschung C 51, no. 11-12 (1996): 772–80. http://dx.doi.org/10.1515/znc-1996-11-1202.

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For azoverdin, the siderophore of Azomonas macrocytogenes ATCC 12334, a pyoverdintype structure has been suggested. We now present evidence that it is actually an isopyoverdin. Also the sequence of the peptide chain has to be revised. Azoverdin comprises, therefore, the chromophore (3S)-5-amino-1,2-dihydro-8,9-dihydroxy-3H -pyrimido[1,2a]quinoline- 3-carboxylic acid whose amino group is bound to a succinamide residue while the carboxyl group is attached to the N -terminus of L-Hse-[2-(R-1-amino-3-hydroxypropyl)-3,4,5,6- tetrahydropyrimidine-65-carboxylic acid]-N5-acetyl-N5,-hydroxy-ᴅ-Orn-ᴅ-Ser

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24

Levendis, Demetrius C., Jeffrey Moffit, Benjamin Staskun, and Theodorus van Es. "Thionyl Chloride-induced Conversion of 1-Ethyl-1,4-dihydro-2-methyl-4-oxoquinoline-3-carboxylic Acids to Highly Functionalised Thieno[3,4-b]quinoline Derivatives." Journal of Chemical Research 23, no. 10 (1999): 614–15. http://dx.doi.org/10.1177/174751989902301014.

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Warming a title acid with SOCl2 gives the corresponding 3,3,9-trichlorothieno[3,4- b]quinolin-1 (3 H)-one whereas reaction at room temperature leads to the intermediate 3,3-dichloro-4-ethylthieno[3,4- b]quinoline-1(3 H),9(4 H)-dione product as established from the respective X-ray crystallographic determinations.

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25

El-Abadelah, Mustafa M., Mohammed M. Abadleh, Firas F. Awwadi, Salim S. Sabri, and Wolfgang Voelter. "Heterocycles [h]-fused onto 4-oxoquinoline-3-carboxylic acid. Part XII: synthesis of 5-fluoro-7-oxodihydo[1,3,4]thiadiazino [5,6-h]quinoline-8-carboxylic acid and ester." Zeitschrift für Naturforschung B 73, no. 1 (2018): 23–28. http://dx.doi.org/10.1515/znb-2017-0136.

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AbstractDirect interaction of dithizone with 7-chloro-6- fluoro-8-nitro-4-oxoquinoline-3-carboxylic acid or with its ester delivered the corresponding novel 1,3,4-thiadiazino [5,6-h]quinoline 3-carboxylic acid, or its ester which was then hydrolyzed to the respective acid. Structures of the latter tricyclic hybrids were deduced from analytical and spectral data and confirmed by single crystal X-ray structure determination of the ester derivative. The free acid showed moderate activity against Staphylococcus aureus with a MIC value of 25 μg mL−1.

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26

Al-As’ad, Randa M., Mustafa M. El-abadelah, Salim S. Sabri, Jalal A. Zahra, and Wolfgang Voelter. "Synthesis of 6-Ethyl-1,2,9-trioxopyrrolo[3,2-f ]quinoline-8-carboxylic Acid." Zeitschrift für Naturforschung B 68, no. 5-6 (2013): 700–706. http://dx.doi.org/10.5560/znb.2013-3009.

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Interaction of 6-amino-1-ethyl-4-oxoquinoline-3-carboxylic ester (7) with chloral hydrate and hydroxylamine hydrochloride gave the corresponding isonitroso-acetamido derivative 8 which, upon treatment with concentrated sulfuric acid, was converted regioselectively into 1,2,9-trioxopyrrolo[ 3,2- f ]quinoline-8-carboxylic acid (3). This novel tricyclic system was isolated in good yield as a stable hydrate 3H. Structural assignments of the new compounds are based on microanalytical and spectral (MS and NMR) data

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27

Nycz, Jacek E., Natalia Martsinovich, Jakub Wantulok, Tieqiao Chen, Maria Książek, and Joachim Kusz. "Synthesis and Spectroscopic Characterization of Selected Water-Soluble Ligands Based on 1,10-Phenanthroline Core." Molecules 29, no. 6 (2024): 1341. http://dx.doi.org/10.3390/molecules29061341.

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Water-soluble ligands based on a 1,10-phenanthroline core are relatively poorly studied compounds. Developing efficient and convenient syntheses of them would result in new interesting applications because of the importance of 1,10-phenanthrolines. In this manuscript, we describe novel and practical ways to introduce a carboxyl and, for the first time, a phenol and dithiocarboxyl group under mild reaction conditions. This strategy enables highly efficient and practical synthesis of suitable organosulfur compounds with high added value, high chemoselectivity, and a broad substrate range. We pre

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28

Brown, CL, MM Harding, GY Krippner, S. Rainone, and LK Webster. "Preparation and Biological Activity of Heteroaryl-Substituted Bile Steroids." Australian Journal of Chemistry 49, no. 1 (1996): 7. http://dx.doi.org/10.1071/ch9960007.

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The synthesis, and growth inhibition studies against the L1210 mouse leukaemia, �MCF-7 human breast cancer and SKOV-3 ovarian carcinoma cell lines, of derivatives of lithocholic acid and cholic acid in which quinoline-3-carboxylate and acridine-9-carboxylate are substituted at the 3 and/or the 24 position are reported. The 3α,24-diheteroaryl-substituted steroid systems, lithocholic acid, cholic acid, quinoline and acridine-9-carboxylic acid showed no significant biological activity against any of the cell lines. In contrast, when either a single quinoline-3-carboxylate or acridine-9-carboxylat

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29

Zozulynets, D. М., A. G. Kaplaushenko, and A. S. Korzhova. "The synthesis of 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol and its interaction with aldehydes." Journal of Organic and Pharmaceutical Chemistry 19, no. 1(73) (2021): 48–52. http://dx.doi.org/10.24959/ophcj.21.188137.

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Aim. To synthesize 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol and study its reactivity in the reactionwith aldehydes.Results and discussion. 4-Amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol was synthesized, and a number of 4-(ethyl, aryl)idenamino derivatives were obtained on its basis.Experimental part. Using a series of four successive reactions based on quinoline-2-carboxylic acid, 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol was synthesized; its interaction with aldehydes allowed to obtain a number of 4-(ethyl, aryl)idenamino derivatives. The structure of all compounds s

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30

Hajalsiddig, Tawassl Tajelsir Hassan, and Ahmed Elsadig Mohammed Saeed. "QSAR and molecular docking studies on 4-quinoline carboxylic acid derivatives as inhibition of vesicular stomatitis virus replication." European Journal of Chemistry 10, no. 1 (2019): 45–51. http://dx.doi.org/10.5155/eurjchem.10.1.45-51.1795.

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The current study describes the development of in silico models based on quantitative structure-activity relationship (QSAR) analysis has been performed on 4-quinoline carboxylic acid derivatives as inhibition capacity of vesicular stomatitis virus replication in Madin Darby canine kidney epithelial cells. A highly descriptive and predictive QSAR model was obtained through the calculation of alignment-independent descriptors using MOE 2009.10 software. For a training set of 20 compounds, the partial least squares analyses result in a model which displays a squared correlation coefficient (r2)

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31

RÃ¶ger, Petra, and Franz Lingens. "Degradation of quinoline-4-carboxylic acid by Microbacterium sp." FEMS Microbiology Letters 57, no. 3 (1989): 279–82. http://dx.doi.org/10.1111/j.1574-6968.1989.tb03349.x.

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32

Brasyunas, V. B., T. A. Andreyanova, T. S. Safonova, N. P. Solov'eva, K. F. Turchin, and Yu N. Sheinker. "Synthesis of quinoline-4-carboxylic acid and its derivatives." Chemistry of Heterocyclic Compounds 24, no. 6 (1988): 670–73. http://dx.doi.org/10.1007/bf00475605.

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Zhang, Liang, Priyabrata Das, Mirco Schmolke, et al. "Inhibition of pyrimidine synthesis reverses viral virulence factor-mediated block of mRNA nuclear export." Journal of Cell Biology 196, no. 3 (2012): 315–26. http://dx.doi.org/10.1083/jcb.201107058.

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The NS1 protein of influenza virus is a major virulence factor essential for virus replication, as it redirects the host cell to promote viral protein expression. NS1 inhibits cellular messenger ribonucleic acid (mRNA) processing and export, down-regulating host gene expression and enhancing viral gene expression. We report in this paper the identification of a nontoxic quinoline carboxylic acid that reverts the inhibition of mRNA nuclear export by NS1, in the absence or presence of the virus. This quinoline carboxylic acid directly inhibited dihydroorotate dehydrogenase (DHODH), a host enzyme

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34

Ouali, M., C. Laboulais, H. Leh, et al. "Tautomers of styrylquinoline derivatives containing a methoxy substituent: computation of their population in aqueous solution and their interaction with RSV integrase catalytic core." Acta Biochimica Polonica 47, no. 1 (2000): 11–22. http://dx.doi.org/10.18388/abp.2000_4058.

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8-Hydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-7-quinoline carboxylic acid and 8-hydroxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethenyl]-7-quinoline carboxylic acid inhibit the processing and strand transfer reactions catalyzed by HIV-1 integrase with an IC50 of 2 microM. Some of their spectral properties are briefly reported. Their fluorescence is so weak that it is of no use in an experimental determination of the binding to the protein and we resorted to computer simulation. Both styrylquinoline derivatives, in their monoanionic form, have several dozens of tautomers and each of these forms ha

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35

Strigáčová, J., D. Hudecová, L' Varečka, A. Lásiková, and D. Végh. "Some biological properties of new quinoline-4-carboxylic acid and quinoline-4-carboxamide derivatives." Folia Microbiologica 45, no. 4 (2000): 305–9. http://dx.doi.org/10.1007/bf02817551.

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36

Mohammed, Shireen. "A Novel Synthetic Route of Fused Tricyclic Framework Quinoline Derivatives from Readily Available Aliphatic Amino Carboxylic Acid Substrates." Oriental Journal of Chemistry 35, no. 2 (2019): 611–17. http://dx.doi.org/10.13005/ojc/350215.

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A novel and an efficient strategy of fused tricyclic quinoline heterocycle compounds from aliphatic amino carboxylic acid substrates is disclosed. The protocol here is proceed over main reaction processes including: cyclization, protection, amidine formation, further cyclization and finally coupling with boronic acid substrate through Suzuki reaction. These reactions afforded the corresponding products in high yields. Furthermore, all synthesized compounds were identiﬁed by spectral data.

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37

ND, Satyanarayan, Sakshith Prasad R, and Harishkumar S. "Design and Synthesis of some 1,3,4-Thiadiazol Amines: Molecular Docking, In-Silico Adme and Antioxidant Properties." Der Pharma Chemica 15, no. 2 (2023): 9. https://doi.org/10.5281/zenodo.13318834.

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Oxidative stress and associated diseases arising from the overproduction of free radicals can be counteracted by designing and creating novel antioxidative agents that can defend the human body against the damage caused by free radicals. In present study, 5-[2-(thiophen-2-yl)quinolin-4- yl]-1,3,4-thiadiazol-2-amine and its derivatives 5(a-e) were designed and synthesised using the 2-(thiophen-2-yl)quinoline-4-carboxylic acid and thiosemicarbazide. Designed targeted antioxidant compounds were docked against the protein PDB-ID: 3VB8 and evaluated the antioxidant activity using the DPPH assay. Th

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38

Satyanarayan, ND, and Prasad R. Sakshith. "Design and Synthesis of some 1,3,4-Thiadiazol Amines: Molecular Docking, In-Silico Adme and Antioxidant Properties." DER PHARMA CHEMICA 15, no. 2 (2023): 9. https://doi.org/10.4172/0975-413X.15.2.35-43.

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Oxidative stress and associated diseases arising from the overproduction of free radicals can be counteracted by designing and creating novel antioxidative agents that can defend the human body against the damage caused by free radicals. In present study, 5-[2-(thiophen-2-yl)quinolin-4- yl]-1,3,4-thiadiazol-2-amine and its derivatives 5(a-e) were designed and synthesised using the 2-(thiophen-2-yl)quinoline-4-carboxylic acid and thiosemicarbazide. Designed targeted antioxidant compounds were docked against the protein PDB-ID: 3VB8 and evaluated the antioxidant activity using the DPPH assay. Th

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39

ND, Satyanarayan, Sakshith Prasad R, and Harishkumar S. "Design and Synthesis of some 1,3,4-Thiadiazol Amines: Molecular Docking, In-Silico Adme and Antioxidant Properties." Der Pharma Chemica 15, no. 2 (2023): 9. https://doi.org/10.5281/zenodo.10934692.

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Oxidative stress and associated diseases arising from the overproduction of free radicals can be counteracted by designing and creating novel antioxidative agents that can defend the human body against the damage caused by free radicals. In present study, 5-[2-(thiophen-2-yl)quinolin-4- yl]-1,3,4-thiadiazol-2-amine and its derivatives 5(a-e) were designed and synthesised using the 2-(thiophen-2-yl)quinoline-4-carboxylic acid and thiosemicarbazide. Designed targeted antioxidant compounds were docked against the protein PDB-ID: 3VB8 and evaluated the antioxidant activity using the DPPH assay. Th

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40

Duduchava, M. R., P. B. Terent'ev, N. F. Piskunkova, and G. A. Bulakhov. "Transformations of quinoline-3-carboxylic acid by the bacteriumRhodococcus opacus." Chemistry of Heterocyclic Compounds 33, no. 10 (1997): 1236–37. http://dx.doi.org/10.1007/bf02290876.

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41

Zhou, Gang, Pauline C. Ting, Grant Wishart, et al. "Discovery of novel quinoline carboxylic acid series as DGAT1 inhibitors." Bioorganic & Medicinal Chemistry Letters 24, no. 7 (2014): 1790–94. http://dx.doi.org/10.1016/j.bmcl.2014.02.028.

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42

Dobrzyńska, Danuta, and Lucjan B. Jerzykiewicz. "Crystal structure of quinoline-2-carboxylic acid quinolinium-2-carboxylate." Journal of Chemical Crystallography 34, no. 1 (2004): 51–55. http://dx.doi.org/10.1023/b:jocc.0000014688.79954.ca.

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43

Hochegger, Patrick, Johanna Faist, Werner Seebacher, et al. "New derivatives of quinoline-4-carboxylic acid with antiplasmodial activity." Bioorganic & Medicinal Chemistry 25, no. 7 (2017): 2251–59. http://dx.doi.org/10.1016/j.bmc.2017.02.043.

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44

Hajalsiddig, Tawassl Tajelsir Hassan, and Ahmed Elsadig Mohammed Saeed. "Synthesis of new 6-substituent 2-phenyl and 2-(furan-2-yl)-3-phenyl-quinoline-4-carboxylic acid derivatives." European Journal of Chemistry 10, no. 1 (2019): 57–63. http://dx.doi.org/10.5155/eurjchem.10.1.57-63.1816.

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A synthesis of substituted quinolines has been achieved by the Doebner reaction which is a three component coupling of arylaldehyde, p-amino-acetophenone and phenyl pyruvic acid. The products of 2,3-diary-6-acetyl-quinoline-4-carboxylic acids were obtained by Claisen Schmidt condensation reaction with aldehydes in the presence of sodium hydroxide in order to give the corresponding α,β-unsaturated carbonyls. The substituted α,β-unsaturated carbonyls were condensed with urea, thiourea, hydrazine, phenyl hydrazine, semicarbazide hydrochloride and ethanolamine to synthesized 2-pyrimidinone, 2-pyri

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45

Abdelwahid, Mazin A. S., Tilal Elsaman, Malik S. Mohamed, Sara A. Latif, Moawia M. Mukhtar, and Magdi A. Mohamed. "Synthesis, Characterization, and Antileishmanial Activity of Certain Quinoline-4-carboxylic Acids." Journal of Chemistry 2019 (February 3, 2019): 1–9. http://dx.doi.org/10.1155/2019/2859637.

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Leishmaniasis is a fatal neglected parasitic disease caused by protozoa of the genusLeishmaniaand transmitted to humans by different species ofphlebotominesandflies. The disease incidence continues to increase due to lack of vaccines and prophylactic drugs. Drugs commonly used for the treatment are frequently toxic and highly expensive. The problem of these drugs is further complicated by the development of resistance. Thus, there is an urgent need to develop new antileishmanial drug candidates. The aim of this study was to synthesize certain quinoline-4-carboxylic acids, confirm their chemica

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Petersen, Jacob P., Ryan D. Brown, Angela M. Silski, Steven A. Corcelli, and S. Alex Kandel. "Complex Structures Resulting from Carboxylic Acid Self-Assembly: Comparison of 2-Naphthoic Acid to Quinaldic Acid and 3-Quinoline Carboxylic Acid." Journal of Physical Chemistry C 123, no. 22 (2019): 13610–14. http://dx.doi.org/10.1021/acs.jpcc.9b01817.

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47

Farrayeh, Batool A., Mustafa M. El-Abadelah, Jalal A. Zahra, Salim F. Haddad, and Wolfgang Voelte. "Heterocycles [h]-Fused onto 4-Oxoquinoline-3-carboxylic Acid. Part X [1]. Synthesis and X-Ray Structure of a Model 4- Oxo[1,4]benzoxazepino[2,3-h]quinoline-3-carboxylic Ester." Zeitschrift für Naturforschung B 68, no. 2 (2013): 187–94. http://dx.doi.org/10.5560/znb.2013-2270.

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Direct interaction of salicylaldehyde oxyanion with ethyl 7-chloro-8-nitro-4-oxoquinoline-3- carboxylate (2) delivered the respective 7-(2-formyl-phenoxy)-8-nitro-4-oxoquinoline-3-carboxylic ester 3. Reductive cyclization of 3 furnished the corresponding 4-oxo-[1,4]benzoxazepino[2,3- h]quinoline-3-carboxylic ester 5. Acid-catalyzed hydrolysis of the esters 3/5 produced the respective acids 4/6. Structural assignments for the new compounds 3 - 6 are supported by microanalytical and spectral (IR, HRMS, NMR) data and confirmed by X-ray structure determination for compound 5. Interestingly, compou

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48

Shen, Jin, Jing-Jing Qian, Jian-Ming Gu, and Xiu-Rong Hu. "Marbofloxacin." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o998—o999. http://dx.doi.org/10.1107/s1600536812009312.

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In the title compound, [systematic name: 9-fluoro-2,3-dihydro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-7H-pyrido[1,2,3-ij][1,2,4]benzoxadiazine-6-carboxylic acid], C17H19FN4O4, the carbonyl and carboxyl groups are coplanar with the quinoline ring, making a dihedral angle of 2.39 (2)°. The piperazine ring adopts a chair conformation and the oxadiazinane ring displays an envelope conformation with the CH2group at the flap displaced by 0.650 (2) Å from the plane through the other five atoms. The molecular structure exhibits anS(6) ring motif, owing to an intramolecular O—H...O hydrogen bond. In

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49

Nugraha, Yuda Prasetya, Haruki Sugiyama, and Hidehiro Uekusa. "Ciprofloxacin salt and salt co-crystal with dihydroxybenzoic acids." Acta Crystallographica Section E Crystallographic Communications 78, no. 3 (2022): 259–63. http://dx.doi.org/10.1107/s2056989022001177.

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The crystal structure of two multi-component crystals of ciprofloxacin [systematic name: 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid], a fluoroquinolone antibiotic, namely, ciprofloxacin 2,6-dihydroxybenzoate salt, C17H19FN3O3 +·C7H5O4 −, (I), and ciprofloxacin hydrochloride–3,5-dihydroxybenzoic–water (1/1/1), C17H19FN3O3 +·Cl−·C7H6O4·H2O, (II), were determined. In (I) and (II), the ciprofloxacin cations are connected via head-to-tail N—H...O hydrogen bonding. Both structures show an alternating layered arrangement between ciprofloxacin and dihydroxybenzoic acid.

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50

Martins, Maria F., Francisco Ribeiro, Ana Borges, et al. "Synthesis of Tricyclic and Tetracyclic Lactone Derivatives of Thieno[2,3-b]pyrazine or Thieno[2,3-b]quinoline: Preliminary Antitumor and Antiparasitic Activity Evaluation." Molecules 30, no. 9 (2025): 1999. https://doi.org/10.3390/molecules30091999.

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Tricyclic and tetracyclic lactone derivatives of thieno[2,3-b]pyrazine or thieno[2,3-b]quinoline, and 2H-pyrones were prepared using different methodologies. Pd/Cu-catalyzed Sonogashira coupling using Et3N as a base, of methyl 7-bromothieno[2,3-b]pyrazine-6-carboxylate and (het)arylalkynes to yield the Sonogashira ester products, gave also the corresponding tricyclic lactones as minor products. However, the major products did not cyclize with TFA. Tricyclic lactones were then obtained by a tandem one-pot Sonogashira coupling and 6-endo-dig lactonization of 7-bromothieno[2,3-b]pyrazine-6-carbox

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