ArticleThe Journal of organic chemistry2013
Synthesis of indole analogues of the natural schweinfurthins.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Synthesis of a Coumarin-Based Analogue of Schweinfurthin F.The Journal of organic chemistry · 2021Article
- β-Indolyloxy Functionalized Aspartate Analogs as Inhibitors of the Excitatory Amino Acid Transporters (EAATs).ACS medicinal chemistry letters · 2020Article
- Synthesis of amide isosteres of schweinfurthin-based stilbenes.Bioorganic & medicinal chemistry · 2017Article
- Calcium and P-glycoprotein independent synergism between schweinfurthins and verapamil.Cancer biology & therapy · 2015Article
- Small molecule schweinfurthins selectively inhibit cancer cell proliferation and mTOR/AKT signaling by interfering with trans-Golgi-network trafficking.Cancer biology & therapy · 2015Article
- Synthesis and structure activity relationships of schweinfurthin indoles.Bioorganic & medicinal chemistry · 2014Article
- Article
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2 authors.
Funding
Abstract
An interest in the schweinfurthins, natural stilbenes with significant antiproliferative activity, has prompted efforts to prepare a set of indole analogues. To approach the desired compounds through a Horner-Wadsworth-Emmons condensation, new indole derivatives bearing a phosphonomethyl substituent in the B-ring were required. The parent indole system with the necessary substitution pattern was obtained through Stobbe condensation and cyclization. A prenyl substituent was incorporated at the C3 position of a 4,6-disubstituted indole through a highly regioselective electrophilic aromatic substitution reaction, while metalation and alkylation provided the C2-prenylated indole. After introduction of the phosphonate group through classical reactions, the new indole phosphonates were found to undergo the desired condensation with nonracemic aldehydes representing the schweinfurthin left half. This approach provides facile access to new heteroaromatic analogues of the natural schweinfurthins and should be applicable to many other natural stilbenes as well.
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