ArticleBioorganic & medicinal chemistry letters2008
Synthesis and anti-breast cancer activities of substituted quinolines.
Article in Bioorganic & medicinal chemistry letters, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 93 citations in OpenAlex.
- Progress in Heterocyclic Hybrids for Breast Cancer Therapy: Emerging Trends, Hybridization Techniques, Mechanistic Pathways and SAR Insights.Mini reviews in medicinal chemistry · 2026Review
- Synthesis, DFT studies on a series of tunable quinoline derivatives.RSC advances · 2024Article
- Quinoline as a Privileged Structure: A Recent Update on Synthesis and Biological Activities.Current topics in medicinal chemistry · 2024Review
- Article
- Facile synthesis andHeliyon · 2021Article
- Recent Advances in the Synthesis and Biological Activity of 8-Hydroxyquinolines.Molecules (Basel, Switzerland) · 2020Review
- An efficient and green reaction of isatins, 3-amino-1-phenyl-2-pyrazolin-5-one (3-amine-1H-pyrazole), and β-diketone in aqueous medium.Molecular diversity · 2017Article
- Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety.Molecules (Basel, Switzerland) · 2016Article
- Induction of Apoptosis by PQ1, a Gap Junction Enhancer that Upregulates Connexin 43 and Activates the MAPK Signaling Pathway in Mammary Carcinoma Cells.International journal of molecular sciences · 2016Article
- Biocide effects of volatile organic compounds produced by potential biocontrol rhizobacteria on Sclerotinia sclerotiorum.Frontiers in microbiology · 2015Article
- Syntheses, neural protective activities, and inhibition of glycogen synthase kinase-3β of substituted quinolines.Bioorganic & medicinal chemistry letters · 2014Article
- The anticancer effect of PQ1 in the MMTV-PyVT mouse model.International journal of cancer · 2014Article
- PQ1, a quinoline derivative, induces apoptosis in T47D breast cancer cells through activation of caspase-8 and caspase-9.Apoptosis : an international journal on programmed cell death · 2013Article
- Design, synthesis, and evaluation of bioactive small molecules.Chemical record (New York, N.Y.) · 2013Article
- Bioavailability and efficacy of a gap junction enhancer (PQ7) in a mouse mammary tumor model.PloS one · 2013Article
- Synthesis of methyl ketones by metabolically engineered Escherichia coli.Journal of industrial microbiology & biotechnology · 2012Article
- Gap Junction Enhancer Potentiates Cytotoxicity of Cisplatin in Breast Cancer Cells.Journal of cancer science & therapy · 2012Article
- The effect of the PQ1 anti-breast cancer agent on normal tissues.Anti-cancer drugs · 2012Article
- Microwave-assisted synthesis of new substituted anilides of quinaldic acid.Molecules (Basel, Switzerland) · 2012Article
- Gap junction enhancer increases efficacy of cisplatin to attenuate mammary tumor growth.PloS one · 2012Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Promising anti-breast cancer agents derived from substituted quinolines were discovered. The quinolines were readily synthesized in a large scale from a sequence of reactions starting from 4-acetamidoanisole. The Michael addition product was isolated as the reaction intermediate in the ring closing reaction of 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy)anisole with methyl vinyl ketone leading to 6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenyloxy)quinoline (14). The amino function of 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline, prepared from 14, was connected to various side chains via alkylation with N-(3-iodopropyl)phthalimide, Michael addition with acrylonitrile, and reductive amination with various heterocycle carboxaldehydes, such as imidazole-4-carboxaldehyde, thiophene-2-carboxaldehyde, and 2-furaldehyde. Effects of the substituted quinolines on cell viability of T47D breast cancer cells using trypan blue exclusion assay were examined. The results showed that the IC(50) value of 6-methoxy-8-[(2-furanylmethyl)amino]-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline is 16+/-3nM, the lowest IC(50) out of all the quinolines tested. IC(50) values of three other quinolines are in the nanomolar range, a desirable range for pharmacological testing.
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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.