The Synthesis, Characterization, and Electrochemical Investigation of Novel Thio- and Alkoxy-Substituted Benzoquinone Derivatives

Ibis, Cemil; Ayla, Sibel Sahınler; Yavuz, Şenol

doi:10.1080/10426507.2013.829833

Cited by 5 publications

(2 citation statements)

References 17 publications

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“…12,26,27 Antimalarial and trypanocidal activities for this class of hybrid compounds were also reported. 22,28,29 Up to our knowledge, there are few electrochemical reports on thionaphthoquinones, 15,19,28,[30][31][32][33] especially in aprotic medium. 19,28,[32][33][34] Most of the quinones and their intermediates, as well as reduced forms, exist inside hydrophobic cell membranes.…”

Section: Introductionmentioning

confidence: 99%

Relationship between Electrochemical Parameters, Cytotoxicity Data against Cancer Cells of 3-Thio-Substituted Nor-Beta-Lapachone Derivatives. Implications for Cancer Therapy

Paiva¹,

Silva²,

Xavier³

et al. 2019

J. Braz. Chem. Soc.

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Electrochemical methods are powerful in the characterization and design of redox-modulating agents. We, herein, report the electrochemical investigation, in aprotic medium, of eleven synthetic 3-thio-substituted-nor-beta-lapachones, along with the determination of cytotoxic activity and correspondent selectivity index, against several cancer cell lines and one normal cell. Four of the quinones are novel compounds. The redox behavior is representative of two independent systems: the easy reduction of the quinone moiety and, at far more negative potential, the reductive cleavage of the C−S−C bonding; and the anodic part controlled by the oxidation of the sulfur moiety. The compounds have shown relevant cytotoxic activity, with emphasis on 3-phenyl-thio-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione (compound 2), which mechanism of molecular action was shown to be related to reactive oxygen species (ROS) release. Despite the absence of a linear correlation, there is a trend: the majority of the thionaphthoquinones, with values of first wave reduction potential, less negative than −0.65 V, were active. The less electrophilic compound (3-(cyclohexylthio)-2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione, cyclohexyl derivative) is also the less cytotoxic toward cancer cells. Agents containing chalcogens and quinones can be used to attack entities with a disturbed redox balance.

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Section: Introductionmentioning

confidence: 99%

Relationship between Electrochemical Parameters, Cytotoxicity Data against Cancer Cells of 3-Thio-Substituted Nor-Beta-Lapachone Derivatives. Implications for Cancer Therapy

Paiva¹,

Silva²,

Xavier³

et al. 2019

J. Braz. Chem. Soc.

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“…[1][2][3] Growing attention has been given to the quinone moiety because of important biologic activity properties such as anticoagulant, [4] antitumor, [5,6] and anticancer [7] activities. Another application area for p-chloranil derivatives is acceptors in charge-transfer complexes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel N-, S-, O-Substituted P-Chloranil Derivatives

Ibis

Ayla

Dogan

et al. 2014

Synthetic Communications

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Reactions of quinones with some aryl phenols and synthesis of new quinone derivatives

Ibis

Ayla

Yavuz

2019

Synthetic Communications

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The Synthesis, Characterization, and Electrochemical Investigation of Novel Thio- and Alkoxy-Substituted Benzoquinone Derivatives

Cited by 5 publications

References 17 publications

Relationship between Electrochemical Parameters, Cytotoxicity Data against Cancer Cells of 3-Thio-Substituted Nor-Beta-Lapachone Derivatives. Implications for Cancer Therapy

Relationship between Electrochemical Parameters, Cytotoxicity Data against Cancer Cells of 3-Thio-Substituted Nor-Beta-Lapachone Derivatives. Implications for Cancer Therapy

Synthesis and Characterization of Novel N-, S-, O-Substituted P-Chloranil Derivatives

Reactions of quinones with some aryl phenols and synthesis of new quinone derivatives

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