ArticleAngewandte Chemie (International ed. in English)2021
Combination of Pseudo-Natural Product Design and Formal Natural Product Ring Distortion Yields Stereochemically and Biologically Diverse Pseudo-Sesquiterpenoid Alkaloids.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 35 citations in OpenAlex.
- Manzamine-A: Unraveling the Chemical and Biological Tapestry of a Marine-Derived Drug Lead.Marine drugs · 2026Review
- Pseudonatural Products for Chemical Biology and Drug Discovery.Journal of medicinal chemistry · 2025Review
- Unifying principles for the design and evaluation of natural product-inspired compound collections.Chemical science · 2025Review
- Identification of readily available pseudo-natural products.RSC medicinal chemistry · 2024Article
- Scaffold Remodelling of Diazaspirotricycles Enables Synthesis of Diverse spChemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Unprecedented Combination of Polyketide Natural Product Fragments Identifies the New Hedgehog Signaling Pathway Inhibitor Grismonone.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- The Time and Place for Nature in Drug Discovery.JACS Au · 2022Review
- Synthesis of 20-Membered Macrocyclic Pseudo-Natural Products Yields Inducers of LC3 Lipidation.Angewandte Chemie (International ed. in English) · 2022Article
- Chemical Evolution of Natural Product Structure.Journal of the American Chemical Society · 2022Article
- Combination of Pseudo-Natural Product Design and Formal Natural Product Ring Distortion Yields Stereochemically and Biologically Diverse Pseudo-Sesquiterpenoid Alkaloids.Angewandte Chemie (International ed. in English) · 2021Article
- Dynamic Catalytic Highly Enantioselective 1,3-Dipolar Cycloadditions.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We describe the synthesis and biological evaluation of a new natural product-inspired compound class obtained by combining the conceptually complementary pseudo-natural product (pseudo-NP) design strategy and a formal adaptation of the complexity-to-diversity ring distortion approach. Fragment-sized α-methylene-sesquiterpene lactones, whose scaffolds can formally be viewed as related to each other or are obtained by ring distortion, were combined with alkaloid-derived pyrrolidine fragments by means of highly selective stereocomplementary 1,3-dipolar cycloaddition reactions. The resulting pseudo-sesquiterpenoid alkaloids were found to be both chemically and biologically diverse, and their biological performance distinctly depends on both the structure of the sesquiterpene lactone-derived scaffolds and the stereochemistry of the pyrrolidine fragment. Biological investigation of the compound collection led to the discovery of a novel chemotype inhibiting Hedgehog-dependent osteoblast differentiation.
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