Publications by authors named "Toni Smeilus"
Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin.
Beilstein J Org Chem
February 2019
Herein, we describe a biomimetic entry to (+)-3-hydroxymethylartemisinin () as well as to the artemisinin derivatives (+)-3-hydroxymethyl-9-desmethylartemisinin () and (+)-3-hydroxymethyl-9--artemisinin (), starting from the known and readily available chiral aldehyde and alkyne . Subsequently, the synthesized compounds have been evaluated for their antimalarial activity against the drug-sensitive NF54 strain. All of them were inactive.
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- The research presents a new, efficient method to synthesize both (-)-artemisinin and its natural counterpart (+)-artemisinin using common chemicals extracted from citronellene.
- The team investigated the action of artemisinin against the Plasmodium falciparum malaria parasite, finding that its antimalarial activity is not dependent on its molecular stereochemistry.
- This innovative approach to synthesizing artemisinin derivatives could lead to new treatments, particularly in the fight against the growing resistance of malaria parasites to existing artemisinin therapies.
Article Synopsis
- A new method for synthesizing C-nor-D-homo steroids is presented, using (+)-Wieland-Miescher ketone as the starting material.
- This technique employs a scalable, selective Nazarov cyclization on chiral aryl vinyl ketones, which simplifies the subsequent functionalization process.
- The ability to perform this reaction on a larger scale allows for the creation of new types of C-nor-D-homo steroids, eliminating the need for traditional methods like steroid rearrangements or lengthy linear reactions.
Several artemisinin derivatives carrying several groups (alkyl, hydroxyalkyl, allyl or azide) at position 9 have been synthesized starting from artemisinin via enolate formation and subsequent reaction with appropriate electrophiles.
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