ArticleEuropean journal of medicinal chemistry2013
N-aryl-6-methoxy-1,2,3,4-tetrahydroquinolines: a novel class of antitumor agents targeting the colchicine site on tubulin.
Article in European journal of medicinal chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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The trial behind it
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Who cites it
20 citing papers in PubMed, 65 citations in OpenAlex.
- Novel Triazoloquinoxaline-Based Tubulin Polymerization Inhibitor Induces Necroptosis and Significantly Inhibits Metastatic Melanoma Tumor Growth.Journal of medicinal chemistry · 2026Article
- Discovery of novel quinazoline derivatives containing trifluoromethyl against cell proliferation by targeting werner helicase.Molecular diversity · 2026Article
- Site-Selective C6-β-Aminoalkylation of Tetrahydroquinolines withThe Journal of organic chemistry · 2026Article
- Synthesis of New Thiazole-Privileged Chalcones as Tubulin Polymerization Inhibitors with Potential Anticancer Activities.Pharmaceuticals (Basel, Switzerland) · 2024Article
- Verubulin (Azixa) Analogues with Increased Saturation: Synthesis, SAR and Encapsulation in Biocompatible Nanocontainers Based on CaPharmaceuticals (Basel, Switzerland) · 2023Article
- Advances in antitumor research of CA-4 analogs carrying quinoline scaffold.Frontiers in chemistry · 2022Review
- X-ray Crystallography-Guided Design, Antitumor Efficacy, and QSAR Analysis of Metabolically Stable Cyclopenta-Pyrimidinyl Dihydroquinoxalinone as a Potent Tubulin Polymerization Inhibitor.Journal of medicinal chemistry · 2021Article
- Discovery of Novel DiarylamideMolecules (Basel, Switzerland) · 2021Article
- Potential of substituted quinazolines to interact with multiple targets in the treatment of cancer.Bioorganic & medicinal chemistry · 2021Article
- Article
- Scaffold Hopping-Driven Optimization of 4-(Quinazolin-4-yl)-3,4-dihydroquinoxalin-2(1ACS medicinal chemistry letters · 2020Article
- In Vivo and Mechanistic Studies on Antitumor Lead 7-Methoxy-4-(2-methylquinazolin-4-yl)-3,4-dihydroquinoxalin-2(1H)-one and Its Modification as a Novel Class of Tubulin-Binding Tumor-Vascular Disrupting Agents.Journal of medicinal chemistry · 2017Article
- An insight into the therapeutic potential of quinazoline derivatives as anticancer agents.MedChemComm · 2017Review
- Crystal structure of 6,7-dimeth-oxy-1-(4-nitro-phen-yl)quinolin-4(1Acta crystallographica. Section E, Crystallographic communications · 2017Article
- Synthesis, biological evaluation, and physicochemical property assessment of 4-substituted 2-phenylaminoquinazolines as Mer tyrosine kinase inhibitors.Bioorganic & medicinal chemistry · 2016Article
- Optimization of N-aryl-6-methoxy-1,2,3,4-tetrahydroquinolines as tubulin polymerization inhibitors.Bioorganic & medicinal chemistry · 2015Article
- Synthesis, anticancer activity and molecular docking studies on a series of heterocyclic trans-cyanocombretastatin analogues as antitubulin agents.European journal of medicinal chemistry · 2015Article
- Tubulin inhibitors: pharmacophore modeling, virtual screening and molecular docking.Acta pharmacologica Sinica · 2014Article
- Optimization of 4-(N-cycloamino)phenylquinazolines as a novel class of tubulin-polymerization inhibitors targeting the colchicine site.Journal of medicinal chemistry · 2014Article
- Recent syntheses of 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions.Molecules (Basel, Switzerland) · 2013Review
Corrections and comments
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Authors and funding
9 authors at 3 institutions in 3 countries.
Funding
Abstract
Structural optimizations of the prior lead 1a led to the discovery of a series of N-aryl-6-methoxy-1,2,3,4-tetrahydroquinoline derivatives as a novel class of tubulin polymerization inhibitors targeted at the colchicine binding site. The most active compound 6d showed extremely high cytotoxicity against a human tumor cell line panel (A549, KB, KBvin, and DU145) with GI50 values ranging from 1.5 to 1.7 nM, significantly more potent than paclitaxel, especially against the drug-resistant KBvin cell line, in the same assays. Analogs 5f, 6b, 6c, and 6e were also quite potent, with a GI50 range of 0.011-0.19 μM. In further studies, active compounds 6b-e and 5f significantly inhibited tubulin assembly, with IC50 values of 0.92-1.0 μM and strongly inhibited colchicine binding to tubulin, with inhibition rates of 75-99% (at 5 μM), comparable with or more potent than combretastatin A-4 (IC50 0.96 μM). Current studies included design, synthesis, and biological evaluations of 24 new compounds (series 3-6). Related SAR analysis, molecular modeling, and evaluation of essential drug-like properties, i.e. water solubility, log P, and in vitro metabolic stability, were also performed.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.