ArticleAngewandte Chemie (International ed. in English)2021
Limonin as a Starting Point for the Construction of Compounds with High Scaffold Diversity.
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 13 papers.
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Who cites it
13 citing papers in PubMed, 30 citations in OpenAlex.
- Random Forest Modeling to Predict Small Molecule Accumulation in Gram-Negative Bacteria.ACS infectious diseases · 2026Article
- An Overview of Limonoids and Other Natural Products Isolated from the Medicinal PlantPlants (Basel, Switzerland) · 2026Review
- Identification of a Selective Anticancer Agent from a Collection of Complex-And-Diverse Compounds Synthesized from Stevioside.Journal of the American Chemical Society · 2025Article
- Raptinal: a powerful tool for rapid induction of apoptotic cell death.Cell death discovery · 2024Review
- Asymmetric total syntheses of sarglamides A, C, D, E, and F.Chemical science · 2024Article
- Enhancing structural diversity through chemical engineering of Ambrosia tenuifolia extract for novel anti-glioblastoma compounds.Scientific reports · 2024Article
- Medium-Sized Ring Expansion Strategies: Enhancing Small-Molecule Library Development.Molecules (Basel, Switzerland) · 2024Review
- Insights into the Mechanism of Action of the Degraded Limonoid Prieurianin.International journal of molecular sciences · 2024Review
- Scaffold Remodelling of Diazaspirotricycles Enables Synthesis of Diverse spChemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Post-Cyclization Skeletal Rearrangements in Plant Triterpenoid Biosynthesis by a Pair of Branchpoint Isomerases.Journal of the American Chemical Society · 2023Article
- Target-Agnostic P-Glycoprotein Assessment Yields Strategies to Evade Efflux, Leading to a BRAF Inhibitor with Intracranial Efficacy.Journal of the American Chemical Society · 2022Article
- Recent Advances in Divergent Synthetic Strategies for Indole-Based Natural Product Libraries.Molecules (Basel, Switzerland) · 2022Review
- 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
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Structurally complex natural products have been a fruitful source for the discovery and development of new drugs. In an effort to construct a compound collection populated by architecturally complex members with unique scaffolds, we have used the natural product limonin as a starting point. Limonin is an abundant triterpenoid natural product and, through alteration of its heptacyclic core ring system using short synthetic sequences, a collection of 98 compounds was created, including multiple members with novel ring systems. The reactions leveraged in the construction of these compounds include novel ring cleavage, rearrangements, and cyclizations, and this work is highlighted by the discovery of a novel B-ring cleavage reaction, a unique B/C-ring rearrangement, an atypical D-ring cyclization, among others. Computational analysis shows that 52 different scaffolds/ring systems were produced during the course of this work, of which 36 are unprecedented. Phenotypic screening and structure-activity relationships identified compounds with activity against a panel of cancer cell lines.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.