Synthesis and pharmacological investigation of new N-hydroxyalkyl-2-aminophenothiazines exhibiting marked MDR inhibitory effect

Takács, Daniella; Egyed, Orsolya; Drahos, László; Szabó, Pál; Jemnitz, Katalin; Szabó, Mónika; Veres, Zsuzsa; Visy, Júlia; Molnár, J.; Riedl, Zsuzsanna; Hajós, György

doi:10.1016/j.bmc.2013.04.034

Cited by 12 publications

(8 citation statements)

References 29 publications

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“…In order to overcome multidrug resistance in cancer treatment, Hajós and colleagues developed a new class of morpholine-containing thiazine-based compounds ( Scheme 17 a). 105 Chlorothiazine 114 was transformed into intermediate amine 115 in excellent yield (92%) through the use of a Pd 2 (dba) 3 / L17 catalyst. Similarly, Pan and co-workers (Novartis) prepared a series of smoothened antagonists in search for a treatment of medulloblastoma and basal cell carcinoma by employing the Pd-catalyzed cross-coupling of morpholine 117 ( Scheme 17 b).…”

Section: Alkylaminesmentioning

confidence: 99%

“…Morpholine is the 17th most common N -heterocycle encountered in commercial pharmaceuticals and C–N cross-coupling is often used for its functionalization. In order to overcome multidrug resistance in cancer treatment, Hajós and colleagues developed a new class of morpholine-containing thiazine-based compounds (Scheme a) . Chlorothiazine 114 was transformed into intermediate amine 115 in excellent yield (92%) through the use of a Pd 2 (dba) 3 / L17 catalyst.…”

Section: Alkylaminesmentioning

confidence: 99%

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Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

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Section: Alkylaminesmentioning

confidence: 99%

Section: Alkylaminesmentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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“…Sulfur atom oxidation ( 7a , 8a and 8b ) significantly enhanced the potential of these compounds as P-glycoprotein inhibitors, with the sulfone derivative 8a exhibiting the greatest potency. Further, the new compounds were nontoxic to hepatocytes [ 28 ]. The antiproliferative activity of similar hybrids developed by the same research group, showed compounds 6c , 7a and 8a as the most active against multidrug-resistant COLO 320 colon adenocarcinoma cells, presenting antiproliferative and potent cytotoxic activity.…”

Section: Anticancer Hybridsmentioning

confidence: 99%

Development of Phenothiazine Hybrids with Potential Medicinal Interest: A Review

et al. 2022

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The molecular hybridization approach has been used to develop compounds with improved efficacy by combining two or more pharmacophores of bioactive scaffolds. In this context, hybridization of various relevant pharmacophores with phenothiazine derivatives has resulted in pertinent compounds with diverse biological activities, interacting with specific or multiple targets. In fact, the development of new drugs or drug candidates based on phenothiazine system has been a promising approach due to the diverse activities associated with this tricyclic system, traditionally present in compounds with antipsychotic, antihistaminic and antimuscarinic effects. Actually, the pharmacological actions of phenothiazine hybrids include promising antibacterial, antifungal, anticancer, anti-inflammatory, antimalarial, analgesic and multi-drug resistance reversal properties. The present review summarizes the progress in the development of phenothiazine hybrids and their biological activity.

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“…Alternatively, early mdr modulators have been derivatized to lower their former cellular toxicity. 25 …”

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confidence: 97%

Discovery of substituted 1,4-dihydroquinolines as novel class of ABCB1 modulators

Hemmer

Krawczyk

Simon

et al. 2015

Bioorganic & Medicinal Chemistry

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Synthesis and pharmacological investigation of new N-hydroxyalkyl-2-aminophenothiazines exhibiting marked MDR inhibitory effect

Cited by 12 publications

References 29 publications

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Development of Phenothiazine Hybrids with Potential Medicinal Interest: A Review

Discovery of substituted 1,4-dihydroquinolines as novel class of ABCB1 modulators

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