Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin
Herein, we describe a biomimetic entry to (+)-3-hydroxymethylartemisinin (2) as well as to the artemisinin derivatives (+)-3-hydroxymethyl-9-desmethylartemisinin (16) and (+)-3-hydroxymethyl-9-epi-artemisinin (18), starting from the known and readily available chiral aldehyde 3 and alkyne 4. Subsequ...
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.15.51 |
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doaj-379503c580da47ac8e98c7bc3aade83b2021-02-02T06:39:55ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-02-0115156757010.3762/bjoc.15.511860-5397-15-51Synthesis and biological investigation of (+)-3-hydroxymethylartemisininToni Smeilus0Farnoush Mousavizadeh1Johannes Krieger2Xingzhao Tu3Marcel Kaiser4Athanassios Giannis5Faculty of Chemistry and Mineralogy, Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04301 Leipzig, GermanyFaculty of Chemistry and Mineralogy, Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04301 Leipzig, GermanyFaculty of Chemistry and Mineralogy, Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04301 Leipzig, GermanyFaculty of Chemistry and Mineralogy, Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04301 Leipzig, GermanyDr. M. Kaiser Swiss Tropical and Public Health Institute, Socinstrasse 57, 4051 Basel, SwitzerlandFaculty of Chemistry and Mineralogy, Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04301 Leipzig, GermanyHerein, we describe a biomimetic entry to (+)-3-hydroxymethylartemisinin (2) as well as to the artemisinin derivatives (+)-3-hydroxymethyl-9-desmethylartemisinin (16) and (+)-3-hydroxymethyl-9-epi-artemisinin (18), starting from the known and readily available chiral aldehyde 3 and alkyne 4. Subsequently, the synthesized compounds have been evaluated for their antimalarial activity against the drug-sensitive P. falciparum NF54 strain. All of them were inactive. In addition, they did not show any toxicity against L6 cells (a primary cell line derived from rat skeletal myoblasts). These results contribute to a better understanding of artemisinins mechanism of action.https://doi.org/10.3762/bjoc.15.51artemisininbiomimetic synthesisDiels–Alder reactionmalariaperoxides |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Toni Smeilus Farnoush Mousavizadeh Johannes Krieger Xingzhao Tu Marcel Kaiser Athanassios Giannis |
| spellingShingle |
Toni Smeilus Farnoush Mousavizadeh Johannes Krieger Xingzhao Tu Marcel Kaiser Athanassios Giannis Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin Beilstein Journal of Organic Chemistry artemisinin biomimetic synthesis Diels–Alder reaction malaria peroxides |
| author_facet |
Toni Smeilus Farnoush Mousavizadeh Johannes Krieger Xingzhao Tu Marcel Kaiser Athanassios Giannis |
| author_sort |
Toni Smeilus |
| title |
Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin |
| title_short |
Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin |
| title_full |
Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin |
| title_fullStr |
Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin |
| title_full_unstemmed |
Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin |
| title_sort |
synthesis and biological investigation of (+)-3-hydroxymethylartemisinin |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2019-02-01 |
| description |
Herein, we describe a biomimetic entry to (+)-3-hydroxymethylartemisinin (2) as well as to the artemisinin derivatives (+)-3-hydroxymethyl-9-desmethylartemisinin (16) and (+)-3-hydroxymethyl-9-epi-artemisinin (18), starting from the known and readily available chiral aldehyde 3 and alkyne 4. Subsequently, the synthesized compounds have been evaluated for their antimalarial activity against the drug-sensitive P. falciparum NF54 strain. All of them were inactive. In addition, they did not show any toxicity against L6 cells (a primary cell line derived from rat skeletal myoblasts). These results contribute to a better understanding of artemisinins mechanism of action. |
| topic |
artemisinin biomimetic synthesis Diels–Alder reaction malaria peroxides |
| url |
https://doi.org/10.3762/bjoc.15.51 |
| work_keys_str_mv |
AT tonismeilus synthesisandbiologicalinvestigationof3hydroxymethylartemisinin AT farnoushmousavizadeh synthesisandbiologicalinvestigationof3hydroxymethylartemisinin AT johanneskrieger synthesisandbiologicalinvestigationof3hydroxymethylartemisinin AT xingzhaotu synthesisandbiologicalinvestigationof3hydroxymethylartemisinin AT marcelkaiser synthesisandbiologicalinvestigationof3hydroxymethylartemisinin AT athanassiosgiannis synthesisandbiologicalinvestigationof3hydroxymethylartemisinin |
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