ArticleBioorganic & medicinal chemistry letters2011
Efficient synthesis and biological evaluation of epiceanothic acid and related compounds.
Article in Bioorganic & medicinal chemistry letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 19 citations in OpenAlex.
- A New Ceanothane-Type Triterpenoid Saponin Isolated fromJournal of microbiology and biotechnology · 2023Article
- Flavonoid Glycosides fromInternational journal of molecular sciences · 2021Article
- Recent advances in natural anti-HIV triterpenoids and analogs.Medicinal research reviews · 2020Review
- Synthesis of acyl oleanolic acid-uracil conjugates and their anti-tumor activity.Chemistry Central journal · 2016Article
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Authors and funding
7 authors at 3 institutions in 3 countries.
Funding
Abstract
Epiceanothic acid (1) is a naturally occurring, but very rare pentacyclic triterpene with a unique pentacyclic triterpene (PT) structure. An efficient synthesis of 1 starting from betulin (3) has been accomplished in 12-steps with a total yield of 10% in our study. Compound 1 and selected synthetic intermediates were further evaluated as anti-HIV-1 agents, inhibitors of glycogen phosphorylase (GP), and cytotoxic agents. Compound 1 exhibited moderate HIV-1 inhibition. Most importantly, compound 5, with an opened A-ring, showed significant GP inhibitory activity with an IC(50) of 0.21 μM, suggesting a potential for development as an anti-diabetic agent. On the other hand, compound 12, with a closed A-ring, showed potent cytotoxicity against A549 and MCF-7 human tumor cell lines, with IC(50) values of 0.89 and 0.33 μM, respectively. These results suggest that the A-ring of PTs is an important pharmacophore that could be modified to involve different biological activities.
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Registered trials
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