Facile synthesis and in vitro anticancer evaluation of a new series of tetrahydroquinoline (original) (raw)
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Journal of Biochemical and Molecular Toxicology, 2018
Due to a great deal of biological activities, quinoline derivatives have drawn attention for synthesis and biological activities in the search for new anticancer drug development. In this work, a variety of substituted (phenyl, nitro, cyano, N-oxide, and methoxy) quinoline derivatives (3-13) were tested in vitro for their biological activity against cancer cell lines, including rat glioblastoma (C6), human cervical cancer cells (HeLa), and human adenocarcinoma (HT29). 6-Bromo-5-nitroquinoline (4), and 6,8-diphenylquinoline (compound 13) showed the greatest antiproliferative activity as compared with the reference drug, 5-fluorouracil (5-FU), while the other compounds showed low antiproliferative activity. 6-Bromo-5-nitroquinoline (4) possesses lower cytotoxic activity than 5-FU in HT29 cell line. Due to its the apoptotic activity 6-Bromo-5-nitroquinoline (4) has the potential to cause cancer cell death.
Acta Pharmaceutica, 2016
As a part of ongoing studies in developing new anticancer agents, novel 1,2-dihydropyridine 4, thienopyridine 5, isoquinolines 6-20, acrylamide 21, thiazolidine 22, thiazoles 23-29 and thiophenes 33-35 bearing a biologically active quinoline nucleus were synthesized. The structure of newly synthesized compounds was confirmed on the basis of elemental analyses and spectral data. All the newly synthesiz ed compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. 2,3-Dihydrothiazole-5-carboxamides 27, 25, 4,5,6,7-tetrahydrobenzo[b]thiophene-3carboxamide (34), 1,2-dihydroisoquinoline-7-carbonitrile (7), 5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide (35), 1,2-dihydroisoquinoline-7-carbonitrile (6), 2-cyano-3-(dimethylamino)-N-(quinolin-3-yl)acrylamide (21), 1,2-dihydroisoquinoline-7-carbonitriles (11) and (8) exhibited higher activity (IC 50 values of 27-45 μmol L-1) compared to doxorubicin (IC 50 47.9 μmol L-1). LQ quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (12), 2-thioxo-2,3-dihydrothiazole-5-carboxamide (28) and quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (15) show activity comparable to doxorubicin, while (quinolin-3-yl)-1,2-dihydroisoquinoline-7-carbonitrile (9), 2,3-dihydrothiazole-5-carboxamide (24), thieno [3,4-c] pyridine-4(5H)-one (5), cyclopenta[b]thiophene-3-carboxamide (33) and (quinolin-3-yl)-6-stryl-1,2dihydroisoquinoline-7-carbonitrile (10) exhibited moderate activity, lower than doxorubicin.
Journal of enzyme inhibition and medicinal chemistry, 2014
This study reports the synthesis of a series of new 2-amino-3-cyano-8-methyl-4-substituted-5,6,7,8-tetrahydroquinolines along with some derived fused-ring systems. Ten compounds have shown remarkable cytotoxic activity against human colon carcinoma HT29, hepatocellular carcinoma HepG2 and Caucasian breast adenocarcinoma MCF7 cell lines. Six compounds showed considerable broad-spectrum cytotoxic activity among which two proved to be the most active derivatives. Likewise, seven compounds from the series were found to exhibit significant antimicrobial activity and three of them proved to be the most active candidates. Two alkylthio-pyrimido quinolines are suggested as possible antimicrobial and anticancer candidates in the present series.
A new and potent class of quinoline derivatives against cancer
Monatshefte für Chemie - Chemical Monthly, 2015
A new class of 4-quinolinylhydrazone derivatives has been synthesized and evaluated for their cytotoxic potential against three cancer cell lines using the MTT assay. Compounds displaying more than 90 % of growth inhibition were evaluated for in vitro anticancer activities against four human cancer cell lines. The results were expressed as the concentrations that induce 50 % inhibition of cell growth (IC 50) in lg/cm 3. These compounds exhibited good cytotoxic activity against at least three cancer cell lines, with IC 50 values between 0.314 and 4.65 lg/ cm 3. These derivatives are useful starting points for further study for new anticancer drugs and confirm the potential of quinoline derivatives as lead compounds in anticancer drug discovery.
Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity
International Journal of Molecular Sciences
This study presents the synthesis, structural characterization, and in vitro evaluation of anticancer activity of some newly benzo[f]quinoline derivatives. The synthesis is facile and efficient, involving two steps: quaternization of nitrogen heterocycle followed by a [3+2] dipolar cycloaddition reaction. The synthesized compounds were characterized by FTIR, NMR, and X-ray diffraction on monocrystal in the case of compounds 6c and 7c. An in vitro single-dose anticancer assay of eighteen benzo[f]quinoline compounds, quaternary salts, and cycloadducts, was performed. The results showed that the most active compounds were quaternary salts 3d and 3f with aromatic R substituents. Quaternary salt 3d revealed non-selective activity against all types of cancer cells, while salt 3f exhibited a highly selective activity against leukemia cells. Compound 3d also presented remarkable cytotoxic efficiency against four distinct types of cancer cells—namely, non-small cell lung cancer HOP–92, melan...
Anticancer Activity of Quinoline Derivatives; An Overview
International Journal of Pharmaceutical Sciences Review and Research
Quinoline, 1-aza naphthalene/benzo pyridine, is nitrogen containing heterocyclic nucleus which is one of the major building blocks of many synthetic drugs. Quinoline derivatives have attracted many scholars’ attention because of their wide range of pharmacological activities such as antimalarial, anticancer, anti-inflammatory, antimicrobial etc. There are so many quinoline derivatives with anticancer activities were reported in various renowned journals. In this review, an attempt is made to compile the latest updates on anticancer activity of quinoline derivatives. Quinoline derivatives plays an important role in anticancer drug development through different mechanism of action like topoisomerase I and II inhibition, proteasome inhibition, antimitotic and tubulin polymerization inhibition etc.
Comprehensive review on current developments of quinoline-based anticancer agents
Arabian Journal of Chemistry, 2016
Among heterocyclic compounds, quinoline scaffold has become an important construction motif for the development of new drugs. Quinoline and its derivatives possess many types of biological activities and have been reported to show significant anticancer activity. Quinoline compounds play an important role in anticancer drug development as they have shown excellent results through different mechanism of action such as growth inhibitors by cell cycle arrest, apoptosis, inhibition of angiogenesis, disruption of cell migration and modulation. A number of quinoline derivatives have been reported till date for their anticancer activity. The present review, summarizes various mono-, di-, tri-, tetra-and heterocyclic substituent quinoline derivatives with potential anticancer activity. Their mechanism of action and possible structure activity relationship has also been discussed.
2022
Colorectal cancer (CRC) is the most commonly diagnosed cancer in Europe and the United States and the second leading cause of cancer related mortality. A therapeutic strategy used for the treatment of CRC involves targeting the intracellular levels of reactive oxygen species (ROS). In this study, we synthesized a series of novel tetrahydroquinolinones and assessed their ability to inhibit CRC growth and proliferation by evoking cellular stress through ROS. Our results revealed that (2-oxo-4-phenyl-5,6,7,8tetrahydroquinolin-8-yl) N-(3-uorophenyl)carbamate (20d) exhibited in vitro antiproliferative activity at micromolar concentrations. The compound also suppressed colony formation and the migration of HCT-116 cells, as well as deregulated the expression of several proteins involved in cell proliferation and metastasis. Furthermore, 20d induced massive oxidative stress by disrupting the balance of cells survival resulting in autophagy via the PI3K/AKT/mTOR signaling pathway. These ndings suggest that this tetrahydroquinolinone can be an ideal lead compound for drug discovery based on quinone derivatives.
American Journal of Applied Sciences, 2011
Problem statement: In continuation to our search for new heterocyclic chemistry based anticancer, the suggestion, synthesis, structure elucidation of some naphthalene, chromene and quinoline derivatives 3-7 were realized herein using 3-methylcyclohexanone 1 as a starting material. Approach: The antitumor activities of the newly synthesized compounds 4-7 were evaluated utilizing 60 different human tumor cell lines, representing leukemia, melanoma, lung, colon, brain, ovary, breast and prostate as well as kidney. Results: Some of the tested compounds exhibited better in vitro antitumor activities at low concentration (log10 GI 50 =-4.7) against the used human tumor cell lines. Conclusion: From the obtained results, we can conclude that cyanopyridine and pyrane moieties fused to 3-methycyclohexane ring are essential for antitumor activities. In the present work, we can suggest that the anticancer activity is due to the presence of nitrogen heterocyclic rings and the presence of the nitrile groups (CN) generally enhancing the activity.