Abstract
[reaction: see text] Propargylamines have been synthesized by a gold(III) salen complex-catalyzed three-component coupling reaction of aldehydes, amines, and alkynes in water in excellent yields at 40 degrees C. With chiral prolinol derivatives as the amine component, excellent diastereoselectivities (up to 99:1) have been attained. This coupling reaction has been applied to the synthesis of propargylamine-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. Cytotoxicities with IC(50) values up to 1.1 microM against a human hepatocellular carcinoma cell line (HepG2) were exhibited by these artemisinin derivatives.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Artemisinins / chemical synthesis
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Artemisinins / chemistry
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Artemisinins / pharmacology*
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Catalysis
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Cell Line, Tumor
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Drug Screening Assays, Antitumor
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Gold / chemistry*
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Humans
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Inhibitory Concentration 50
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Lactones / chemical synthesis
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Lactones / chemistry
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Lactones / pharmacology*
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Molecular Structure
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Pargyline / analogs & derivatives*
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Pargyline / chemical synthesis
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Pargyline / chemistry
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Propylamines / chemical synthesis*
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Propylamines / chemistry
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Sesquiterpenes / chemical synthesis
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Sesquiterpenes / chemistry
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Sesquiterpenes / pharmacology*
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Stereoisomerism
Substances
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Artemisinins
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Lactones
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Propylamines
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Sesquiterpenes
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propargylamine
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Gold
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Pargyline
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artemisin