Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54
Quinones and quinols are secondary metabolites of higher plants that are associated with many biological activities. The oxidative dearomatization of phenols induced by hypervalent iodine(III) reagents has proven to be a very useful synthetic approach for the preparation of these compounds, which ar...
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| Format: | Article |
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/19/6559 |
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| author | Nina Scheiber Gregor Blaser Eva-Maria Pferschy-Wenzig Marcel Kaiser Pascal Mäser Armin Presser |
| author_facet | Nina Scheiber Gregor Blaser Eva-Maria Pferschy-Wenzig Marcel Kaiser Pascal Mäser Armin Presser |
| author_sort | Nina Scheiber |
| collection | DOAJ |
| description | Quinones and quinols are secondary metabolites of higher plants that are associated with many biological activities. The oxidative dearomatization of phenols induced by hypervalent iodine(III) reagents has proven to be a very useful synthetic approach for the preparation of these compounds, which are also widely used in organic synthesis and medicinal chemistry. Starting from several substituted phenols and naphthols, a series of cyclohexadienone and naphthoquinone derivatives were synthesized using different hypervalent iodine(III) reagents and evaluated for their in vitro antiprotozoal activity. Antiprotozoal activity was assessed against <i>Plasmodium falciparum</i> NF54 and <i>Trypanosoma brucei rhodesiense</i> STIB900. Cytotoxicity of all compounds towards L6 cells was evaluated and the respective selectivity indices (SI) were calculated. We found that benzyl naphthoquinone <b>5c</b> was the most active and selective molecule against <i>T. brucei rhodesiense</i> (IC<sub>50</sub> = 0.08 μM, SI = 275). Furthermore, the antiprotozoal assays revealed no specific effects. In addition, some key physicochemical parameters of the synthesised compounds were calculated. |
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| format | Article |
| id | doaj.art-1f327826012141e9b9075e3ef67e8f7a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T21:23:24Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-1f327826012141e9b9075e3ef67e8f7a2023-11-23T21:13:24ZengMDPI AGMolecules1420-30492022-10-012719655910.3390/molecules27196559Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54Nina Scheiber0Gregor Blaser1Eva-Maria Pferschy-Wenzig2Marcel Kaiser3Pascal Mäser4Armin Presser5Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, AustriaInstitute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, AustriaInstitute of Pharmaceutical Sciences, Pharmacognosy, University of Graz, Beethovenstrasse 8, 8010 Graz, AustriaSwiss Tropical and Public Health Institute, Kreuzstrasse 2, 4123 Allschwil, SwitzerlandSwiss Tropical and Public Health Institute, Kreuzstrasse 2, 4123 Allschwil, SwitzerlandInstitute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, AustriaQuinones and quinols are secondary metabolites of higher plants that are associated with many biological activities. The oxidative dearomatization of phenols induced by hypervalent iodine(III) reagents has proven to be a very useful synthetic approach for the preparation of these compounds, which are also widely used in organic synthesis and medicinal chemistry. Starting from several substituted phenols and naphthols, a series of cyclohexadienone and naphthoquinone derivatives were synthesized using different hypervalent iodine(III) reagents and evaluated for their in vitro antiprotozoal activity. Antiprotozoal activity was assessed against <i>Plasmodium falciparum</i> NF54 and <i>Trypanosoma brucei rhodesiense</i> STIB900. Cytotoxicity of all compounds towards L6 cells was evaluated and the respective selectivity indices (SI) were calculated. We found that benzyl naphthoquinone <b>5c</b> was the most active and selective molecule against <i>T. brucei rhodesiense</i> (IC<sub>50</sub> = 0.08 μM, SI = 275). Furthermore, the antiprotozoal assays revealed no specific effects. In addition, some key physicochemical parameters of the synthesised compounds were calculated.https://www.mdpi.com/1420-3049/27/19/6559oxidative dearomatizationhypervalent iodinecyclohexadienonesantiprotozoal activityphysicochemical parameters |
| spellingShingle | Nina Scheiber Gregor Blaser Eva-Maria Pferschy-Wenzig Marcel Kaiser Pascal Mäser Armin Presser Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54 Molecules oxidative dearomatization hypervalent iodine cyclohexadienones antiprotozoal activity physicochemical parameters |
| title | Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54 |
| title_full | Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54 |
| title_fullStr | Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54 |
| title_full_unstemmed | Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54 |
| title_short | Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54 |
| title_sort | efficient oxidative dearomatisations of substituted phenols using hypervalent iodine iii reagents and antiprotozoal evaluation of the resulting cyclohexadienones against i t b rhodesiense i and i p falciparum i strain nf54 |
| topic | oxidative dearomatization hypervalent iodine cyclohexadienones antiprotozoal activity physicochemical parameters |
| url | https://www.mdpi.com/1420-3049/27/19/6559 |
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