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Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin.

ABSTRACT: 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.

SUBMITTER: Smeilus T

PROVIDER: S-EPMC6404461 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin.

Smeilus Toni T Mousavizadeh Farnoush F Krieger Johannes J Tu Xingzhao X Kaiser Marcel M Giannis Athanassios A

Beilstein journal of organic chemistry 20190227

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 ...[more]

PMID: 30873241

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