Synthesis of 6‐ and 8‐Halogenosubstituted 3‐Quinoline‐Sulfonic Acid Derivatives[1]

Marciniec, Krzysztof; Maślankiewicz, Andrzej; Maślankiewicz, Maria J.

doi:10.1002/jhet.2079

Cited by 7 publications

(4 citation statements)

References 17 publications

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“…This process proceeded stepwise by halogen substitution resulting in 3,6-dimethylthioquinoline (not shown in Scheme 2 ), which was then S-dealkylated to respective azinedithiolate 8 . This can be trapped by alkylation with propargyl bromide to produce dipropargylthioquinoline 11, or oxidtively chlorinated to 3,6-dichlorosulfonylquinoline 9 as described previously [ 34 ].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Anti-Breast Cancer Activity, and Molecular Docking Study of a New Group of Acetylenic Quinolinesulfonamide Derivatives

et al. 2017

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In this study, a series of regioisomeric acetylenic sulfamoylquinolines are designed, synthesized, and tested in vitro for their antiproliferative activity against three human breast cacer cell lines (T47D, MCF-7, and MDA-MB-231) and a human normal fibroblast (HFF-1) by 4-[3-(4-iodophenyl)-2-(4-nitrophenyl)-2H-5-tetrazolio]-1,3-benzene disulfonate (WST-1) assay. The antiproliferative activity of the tested acetylenic quinolinesulfonamides is comparable to that of cisplatin. The bioassay results demonstrate that most of the tested compounds show potent antitumor activities, and that some compounds exhibit better effects than the positive control cisplatin against various cancer cell lines. Among these compounds, 4-(3-propynylthio)-7-[N-methyl-N-(3-propynyl)sulfamoyl]quinoline shows significant antiprolierative activity against T47D cells with IC50 values of 0.07 µM. In addition, 2-(3-Propynylthio)-6-[N-methyl-N-(3-propynyl)sulfa-moyl]quinoline and 2-(3-propynylseleno)-6-[N-methyl-N-(3-propynyl)sulfamoyl]quinoline display highly effective atitumor activity against MDA-MB-231 cells, with IC50 values of 0.09 and 0.50 µM, respectively. Furthermore, most of the tested compounds show a weak cytotoxic effect against the normal HFF-1 cell line. Additionally, in order to suggest a mechanism of action for their activity, all compounds are docked into the binding site of two human cytochrome P450 (CYP) isoenzymes. These data indicate that some of the title compounds display significant cytotoxic activity, possibly targeting the CYPs pathways.

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Section: Resultsmentioning

confidence: 99%

“…Silica gel 60 was used as a solid phase, and ethyl acetate was used as the eluent. The starting compounds, chloro-quinolinesulfochlorides 1a – f and 3,6-dichlorosulfonylquinoline 9 , were obtained according to previously described methods [ 32 , 33 , 34 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Anti-Breast Cancer Activity, and Molecular Docking Study of a New Group of Acetylenic Quinolinesulfonamide Derivatives

et al. 2017

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“…To illustrate the practicability of the developed strategy, we applied bromination for the modification of quinoline derivatives containing biomolecular fragments, such as terpene, protected sugar, and steroid, to yield the desired products in moderate to good yields ( 42–46 , 41–89%). Additionally, the constructed C–Br bond can be easily transformed into other useful C–X bonds, such as C–O, C–S, C–B, C–CCR, and C–P bonds ( 47 – 55 ) using common methods. Notably, most cases displayed selective monofunctionalization and retained the other halogen site.…”

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confidence: 99%

Radical meta-C–H Halogenation of Azines via N-Benzyl Activation Strategy

Tang,

Li,

et al. 2024

Org. Lett.

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Regioselective halogenation of six-membered N-heteroarenes is crucial for precise functional derivatization. We present a meta-selective halogenation method for pyridines, quinolines, and isoquinolines via electrophilic halogen radical addition utilizing an N-benzyl activation strategy. This method achieves C3-and C5-dihalogenation in pyridines, C3-and C6-dihalogenation in quinolines, and C3-monohalogenation in isoquinolines. The feasibility and potential applications of this method were validated through scale-up reactions and the bromination of quinoline derivatives with biomolecular fragments.

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“…[5] The synthesis of sulfides with as aturated carbon skeleton receives increasing attention, [6] especially in pharmaceutical areas, due in part to higher hydrophilic nature of alkyl groups than aromatic groups. [6d-f] Conventional approaches for alkyl-sulfur bond formation are mainly based on substitution reactions of nucleophilic sulfur reagents such as metal sulfides, [7] thiosulfates, [8] thiourea, [9] thiol derivatives [10] with electrophilic alkylating reagents. The reactions of inverse polarity,i .e .b etween electrophilic sulfuration reagents such as sulfenyl halides, [11] or disulfides [12] and alkyl nucleophiles or olefins also make convenient routes.…”

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confidence: 99%

Alkyl Sulfides as Promising Sulfur Sources: Metal‐Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides

Liu

Qiu

Zhu

et al. 2018

Chemistry An Asian Journal

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Synthesis of 6‐ and 8‐Halogenosubstituted 3‐Quinoline‐Sulfonic Acid Derivatives[1]

Cited by 7 publications

References 17 publications

Synthesis, Anti-Breast Cancer Activity, and Molecular Docking Study of a New Group of Acetylenic Quinolinesulfonamide Derivatives

Synthesis, Anti-Breast Cancer Activity, and Molecular Docking Study of a New Group of Acetylenic Quinolinesulfonamide Derivatives

Radical meta-C–H Halogenation of Azines via N-Benzyl Activation Strategy

Alkyl Sulfides as Promising Sulfur Sources: Metal‐Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides

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