ArticleJournal of the American Chemical Society2018
Total Synthesis, Biological Evaluation, and Target Identification of Rare Abies Sesquiterpenoids.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 46 citations in OpenAlex.
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- Total synthesis and target identification of marine cyclopiane diterpenes.Nature communications · 2024Article
- Ten-Step Total Synthesis of (±)-Phaeocaulisin A Enabled by Cyclopropanol Ring-Opening Carbonylation.Journal of the American Chemical Society · 2024Article
- Concise Total Syntheses of (Journal of the American Chemical Society · 2024Article
- Natural Product-Inspired Molecules for Covalent Inhibition of SHP2 Tyrosine Phosphatase.Tetrahedron · 2024Article
- Biomimetic Synthesis and Chemical Proteomics Reveal the Mechanism of Action and Functional Targets of Phloroglucinol Meroterpenoids.Journal of the American Chemical Society · 2024Article
- Convergent and Efficient Total Synthesis of (+)-Heilonine Enabled by C-H Functionalizations.Journal of the American Chemical Society · 2024Article
- Total Synthesis of Terpenes and Their Biological Significance: A Critical Review.Pharmaceuticals (Basel, Switzerland) · 2022Review
- Beshanzoides A-D, unprecedented cycloheptanone-containing polyketides fromRSC advances · 2021Article
- Flow Chemistry-Enabled Divergent and Enantioselective Total Syntheses of Massarinolin A, Purpurolides B, D, E, 2,3-Deoxypurpurolide C, and Structural Revision of Massarinolin A.Angewandte Chemie (International ed. in English) · 2021Article
- Total Synthesis and Target Identification of the Curcusone Diterpenes.Journal of the American Chemical Society · 2021Article
- BMPQ-1 binds selectively to (3+1) hybrid topologies in human telomeric G-quadruplex multimers.Nucleic acids research · 2020Article
- Total Synthesis of trans-Resorcylide via Macrocyclic Stille Carbonylation.The Journal of antibiotics · 2019Article
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
Abiespiroside A (1), beshanzuenone C (2), and beshanzuenone D (3) belong to the Abies sesquiterpenoid family. Beshanzuenones C (2) and D (3) are isolated from the critically endangered Chinese fir tree species Abies beshanzuensis and demonstrated weak inhibiting activity against protein tyrosine phosphatase 1B (PTP1B). We describe herein the first total syntheses of these Abies sesquiterpenoids relying on the sustainable and inexpensive chiral pool molecule (+)-carvone. The syntheses feature a palladium-catalyzed hydrocarbonylative lactonization to install the 6,6-fused bicyclic ring system and a Dreiding-Schmidt reaction to build the oxaspirolactone moiety of these target molecules. Our chemical total syntheses of these Abies sesquiterpenoids have enabled (i) the validation of beshanzuenone C's weak PTP1B inhibiting potency, (ii) identification of new synthetic analogs with promising and selective protein tyrosine phosphatase SHP2 inhibiting potency, and (iii) preparation of azide-tagged probe molecules for target identification via a chemoproteomic approach. The latter has resulted in the identification and evaluation of DNA polymerase epsilon subunit 3 (POLE3) as one of the novel cellular targets of these Abies sesquiterpenoids and their analogs. More importantly, via POLE3 inactivation by probe molecule 29 and knockdown experiment, we further demonstrated that targeting POLE3 with small molecules may be a novel strategy for chemosensitization to DNA damaging drugs such as etoposide in cancer.
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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 Socratic graph.