Synthesis of 4-Hydroxyquinolines. VIII. Some Halogen Containing 4-Aminoquinoline Derivatives<sup>1</sup>

Snyder, H. R.; Freier, Herbert E.; Kovacic, Peter; Heyningen, E. M. Van

doi:10.1021/ja01194a061

Cited by 40 publications

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“…As shown in the Scheme 1, the derivatives were synthesized using a three-step procedure that involves the condensation of anilines 7 with diethyl ethoxymethylenemalonate (EMME)in refluxing ethanol followed by thermal cyclization of the aniline acrylate intermediates 8 , according to Gould-Jacobs methodology [17,18,19,20,21]. A nucleophilic substitution reaction between oxoquinolines 9 and the appropriate amines in diphenyl ether as solvent affords the respective carboxamides 10 – 18 (Table 1) in 30%–98% yields.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Cytotoxicity and Mechanistic Evaluation of 4-Oxoquinoline-3-carboxamide Derivatives: Finding New Potential Anticancer Drugs

et al. 2014

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As part of a continuing search for new potential anticancer candidates, we describe the synthesis, cytotoxicity and mechanistic evaluation of a series of 4-oxoquinoline-3-carboxamide derivatives as novel anticancer agents. The inhibitory activity of compounds 10-18 was determined against three cancer cell lines using the MTT colorimetric assay. The screening revealed that derivatives 16b and 17b exhibited significant cytotoxic activity against the gastric cancer cell line but was not active against a normal cell line, in contrast to doxorubicin, a standard chemotherapeutic drug in clinical use. Interestingly, no hemolytical activity was observed when the toxicity of 16b and 17b was tested against blood cells. The in silico and in vitro mechanistic evaluation indicated OPEN ACCESSMolecules 2014, 19 6652 the potential of 16b as a lead for the development of novel anticancer agents against gastric cancer cells.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Cytotoxicity and Mechanistic Evaluation of 4-Oxoquinoline-3-carboxamide Derivatives: Finding New Potential Anticancer Drugs

et al. 2014

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“…High-resolution mass (HRMS) spectral were performed on an Agilent Technologies 6530 Accurate-Mass Q-TOF Mass Spectrometer (Santa Clara, CA, USA). Compounds A ( A01 – A09 ), B (B01 – B09 ), C ( C01 – C09 ), D ( D01 – D09 ) and E ( E01 – E09 ) [ 19 , 21 , 47 , 48 , 49 , 50 , 51 ] were previously prepared.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Molecular Docking Analysis and Biological Evaluations of 4-[(Quinolin-4-yl)amino]benzamide Derivatives as Novel Anti-Influenza Virus Agents

Zhang

Tang

Meng

et al. 2022

IJMS

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In this study, a series of 4-[(quinolin-4-yl)amino]benzamide derivatives as the novel anti-influenza agents were designed and synthesized. Cytotoxicity assay, cytopathic effect assay and plaque inhibition assay were performed to evaluate the anti-influenza virus A/WSN/33 (H1N1) activity of the target compounds. The target compound G07 demonstrated significant anti-influenza virus A/WSN/33 (H1N1) activity both in cytopathic effect assay (EC50 = 11.38 ± 1.89 µM) and plaque inhibition assay (IC50 = 0.23 ± 0.15 µM). G07 also exhibited significant anti-influenza virus activities against other three different influenza virus strains A/PR/8 (H1N1), A/HK/68 (H3N2) and influenza B virus. According to the result of ribonucleoprotein reconstitution assay, G07 could interact well with ribonucleoprotein with an inhibition rate of 80.65% at 100 µM. Furthermore, G07 exhibited significant activity target PA−PB1 subunit of RNA polymerase according to the PA−PB1 inhibitory activity prediction by the best pharmacophore Hypo1. In addition, G07 was well drug-likeness based on the results of Lipinski’s rule and ADMET prediction. All the results proved that 4-[(quinolin-4-yl)amino]benzamide derivatives could generate potential candidates in discovery of anti-influenza virus agents.

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“…The compounds tested in the present study (4a-k) were previously synthesized through the Gould-Jacobs methodology [22–25], using a three-step procedure that involved the condensation of anilines 1a-k with diethyl ethoxymethylenemalonate (DEEMM) in refluxing ethanol followed by thermal cyclization of the aniline acrylate intermediates 2a-k, as shown in the Figure 1. The nucleophilic substitution reaction between oxoquinolines 3a-k and the benzylamine in diphenyl ether, according to our previous works [19,20] afforded the respective 4-oxoquinolines-3-carboxamides 4a-k (Table 1) in 98–55% yields.…”

Section: Methodsmentioning

confidence: 99%

Antiviral Activity of 4-Oxoquinoline-3 - Carboxamide Derivatives against Bovine Herpesvirus Type 5

et al. 2020

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Background Bovine herpesvirus type 5 is an important agent of meningoencephalitis in cattle and has been identified in outbreaks of bovine neurological disease in several Brazilian states. In recent years, oxoquinoline derivatives have become an important focus in antiviral drug research. Methods The cytotoxicity and anti BoHV-5RJ42/01 activity of a set of synthetic 4-oxoquinoline derivatives 4a-k were assayed on Madin–Darby Bovine Kidney cell and antiviral activity by plaque reduction assay. Results: The most promising substance (4h) exhibited CC50 and EC50 values of 1,239 μM ±5.5 and 6.0 μM ±1.5, respectively, with an SI =206. Two other compounds 4j (CC50 = 35 μM ±2 and EC50 = 24 μM ±7.0) and 4k (CC50= 55 μM ±2 and EC50 = 24 μM ±5.1) presented similar inhibitory profile and selectivity indexes of 1.4 and 2.9, respectively. The results of the time-of-addition studies revealed expressive reduction of virus production (≥80%) in different stages of virus replication cycle except for compound 4h that slightly inhibited virus yield in the first 2 h post infection, but it showed expressive virus inhibition after this time. Conclusions All three compounds slightly interact with the virus on the virucidal assay and they are not able to block virus attachment and penetration. Antiviral effect of oxoquinoline 4h was more prominent than acyclovir which leads us to suggest compound 4h as a promising molecule for further anti-BoHV-5 drug design.

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Synthesis of 4-Hydroxyquinolines. VIII. Some Halogen Containing 4-Aminoquinoline Derivatives¹

Cited by 40 publications

References 0 publications

Synthesis, Cytotoxicity and Mechanistic Evaluation of 4-Oxoquinoline-3-carboxamide Derivatives: Finding New Potential Anticancer Drugs

Synthesis, Cytotoxicity and Mechanistic Evaluation of 4-Oxoquinoline-3-carboxamide Derivatives: Finding New Potential Anticancer Drugs

Design, Synthesis, Molecular Docking Analysis and Biological Evaluations of 4-[(Quinolin-4-yl)amino]benzamide Derivatives as Novel Anti-Influenza Virus Agents

Antiviral Activity of 4-Oxoquinoline-3 - Carboxamide Derivatives against Bovine Herpesvirus Type 5

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Synthesis of 4-Hydroxyquinolines. VIII. Some Halogen Containing 4-Aminoquinoline Derivatives1

Cited by 40 publications

References 0 publications

Synthesis, Cytotoxicity and Mechanistic Evaluation of 4-Oxoquinoline-3-carboxamide Derivatives: Finding New Potential Anticancer Drugs

Synthesis, Cytotoxicity and Mechanistic Evaluation of 4-Oxoquinoline-3-carboxamide Derivatives: Finding New Potential Anticancer Drugs

Design, Synthesis, Molecular Docking Analysis and Biological Evaluations of 4-[(Quinolin-4-yl)amino]benzamide Derivatives as Novel Anti-Influenza Virus Agents

Antiviral Activity of 4-Oxoquinoline-3 - Carboxamide Derivatives against Bovine Herpesvirus Type 5

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Synthesis of 4-Hydroxyquinolines. VIII. Some Halogen Containing 4-Aminoquinoline Derivatives¹