Cancer preventive agents, Part 2: Synthesis and evaluation of 2-phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives as novel antitumor promoters

Nakamura, Seikou; Kozuka, Mutsuo; Bastow, Kenneth F.; Tokuda, Harukuni; Nishino, Hoyoku; Suzuki, Madoka; Tatsuzaki, Jin; Natschke, Susan L. Morris; Kuo, Sheng Chu; Lee, Kuo Hsiung̀

doi:10.1016/j.bmc.2005.04.078

Cited by 44 publications

(18 citation statements)

References 13 publications

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“… a TPA concentration is 32 pmol/mL b logCureP represents a log10 transformed response fingerprint values, as described in reference 45 c Values in parentheses represent viability percentages of Raji cells. For the determination of cytotoxicity, the cell viability is required greater than 60 %…”

Section: Figmentioning

confidence: 99%

Design, synthesis and experimental validation of novel potential chemopreventive agents using random forest and support vector machine binary classifiers

Sprague

Shi

Kim

et al. 2014

J Comput Aided Mol Des

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Compared to the current knowledge on cancer chemotherapeutic agents, only limited information is available on the ability of organic compounds, such as drugs and/or natural products, to prevent or delay the onset of cancer. In order to evaluate chemical chemopreventive potentials and design novel chemopreventive agents with low to no toxicity, we developed predictive computational models for chemopreventive agents in this study. First, we curated a database containing over 400 organic compounds with known chemoprevention activities. Based on this database, various random forest and support vector machine binary classifiers were developed. All of the resulting models were validated by cross validation procedures. Then, the validated models were applied to virtually screen a chemical library containing around 23,000 natural products and derivatives. We selected a list of 148 novel chemopreventive compounds based on the consensus prediction of all validated models. We further analyzed the predicted active compounds by their ease of organic synthesis. Finally, 18 compounds were synthesized and experimentally validated for their chemopreventive activity. The experimental validation results paralleled the cross validation results, demonstrating the utility of the developed models. The predictive models developed in this study can be applied to virtually screen other chemical libraries to identify novel lead compounds for the chemo-prevention of cancers.

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Section: Figmentioning

confidence: 99%

Design, synthesis and experimental validation of novel potential chemopreventive agents using random forest and support vector machine binary classifiers

Sprague

Shi

Kim

et al. 2014

J Comput Aided Mol Des

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“…27 In other work on phenyl quinolines, 2-(4-phenylquinolin-2-yl)phenol derivatives produced significant anti-inflammatory, analgesic and antipyretic activities and demonstrated efficient inhibition of the COX-2 enzyme. 28 A number of substituted 2-phenylquinolines displayed superior ERβ affinity in a cellbased transcriptional assay, 29 potent antiplatelet activities, 30 antimitotic activity, [31][32][33] and antiproliferative activity against the growth of certain cancer cells such as HCT-116 (colon cancer), MCF7 (breast cancer), and MDA-MB-435 (breast cancer) with low GI 50 values. 34 Previously, we carried out the bromination of 1,2,3,4-tetrahydroquinoline (1) 15,35,36 with molecular bromine leading to the formation of polyfunctional quinoline derivatives, which was followed by transformation into their respective derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of aryl-substituted quinolines and tetrahydroquinolines through Suzuki–Miyaura coupling reactions

Ökten

2019

Journal of Chemical Research

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The synthesis and characterization of substituted (trifluoromethoxy, thiomethyl, and methoxy) phenyl quinolines is described. Dichlorobis(triphenylphosphine)palladium(II)-catalyzed Suzuki–Miyaura cross-coupling of 6-bromo- and 6,8-dibromo-1,2,3,4-tetrahydroquinolines, 5-bromo-8-methoxyquinoline, and 5,7-dibromo-8-methoxyquinoline with substituted phenylboronic acids affords the corresponding 6-aryl- (13a–d), 6,8-diaryl- (14a–c), 5-aryl- (15), and 5,7-diaryl- (16b, c) tetrahydroquinolines and quinolines in high yields (68%–82%). The structures of all the products are characterized by 1H NMR, 13C NMR,19F NMR, and Fourier transform infrared spectroscopy and by elemental analysis.

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“…The development of antibiotic quinolone begun in 1962 with the discovery of nalidixic acid which was used to treat urinary tract infections (Lesher et al, 1962). Many diversely substituted 4-quinolones have been extensively investigated as anti-tumour (Nakamura et al, 2005), anti-viral (Santos et al, 2009), anti-diabetic (Edmont et al, 2000), anti-trypanosomal (Wube et al, 2011) and anti-malarial agents (Vinayaka et al, 2014). As part of our studies in this area, the title compound was synthesized to study its crystal structure.…”

Section: Structure Descriptionmentioning

confidence: 99%

2-(2-Chlorobenzoyl)-1-(3,4-dimethoxyphenyl)-3-iodoquinolin-4(1H)-one

Shankar¹,

Chandra

Vinayaka

et al. 2017

IUCr Data

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In the title compound C 24 H 17 ClINO 4 , the iodoquinolinyl moiety (r.m.s. deviation = 0.044 Å ) makes dihedral angles of 87.44 (10) and 88.64 (10) with the chloro-and methoxy-substituted benzene rings, respectively. The methoxy groups are present in synperiplanar and antiperiplanar conformations with respect to the benzene ring they are bound to, as indicated by the C-C-O-C torsion angle values of À16.2 (3) and 177.6 (2) , respectively. The crystal structure features relatively strong methoxybenzene-C-HÁ Á ÁO(quinolinyl) hydrogen bonds, leading to helical supramolecular chains along the a-axis direction. Additional C-HÁ Á ÁO interactions along with -stacking [intercentroid distance = 3.6070 (16) Å between quinolyl-NC 5 and C 6 rings] consolidate the three-dimensional molecular packing.

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Cancer preventive agents, Part 2: Synthesis and evaluation of 2-phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives as novel antitumor promoters

Cited by 44 publications

References 13 publications

Design, synthesis and experimental validation of novel potential chemopreventive agents using random forest and support vector machine binary classifiers

Design, synthesis and experimental validation of novel potential chemopreventive agents using random forest and support vector machine binary classifiers

Synthesis of aryl-substituted quinolines and tetrahydroquinolines through Suzuki–Miyaura coupling reactions

2-(2-Chlorobenzoyl)-1-(3,4-dimethoxyphenyl)-3-iodoquinolin-4(1H)-one

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