Neolaxiflorin L (NL) is a low-abundant Isodon 7,20-epoxy- ent-kuarenoid and was found to be a promising anticancer drug candidate in our previous study. In order to study its structure-activity relationship (SAR), a diversity-oriented synthetic route toward two libraries of (±)-NL analogs, including analogs containing different functionalities in the same 7,20-epoxy- ent-kuarene skeleton and analogs with skeletal changes, has been developed. The results of this total synthesis-enabled SAR successfully led to a bioactive alkyne-tagged NL derivative, which could be a useful probe for proteomics studies.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.9b00748 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Total Syntheses and Stereochemical Assignment of Acremolides A and B.
Molecules
July 2024
State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
The absolute stereochemical configurations of acremolides A and B were predicted by a biochemistry-based rule and unambiguously confirmed through their total syntheses. The features of the total syntheses include sequential Krische's Ir-catalyzed crotylation, Brown's borane-mediated crotylation, Mitsunobu esterification reaction, and cross-metathesis reaction. The efficient total synthesis enabled clear validation of the predicted stereochemistry for acremolides A and B.
View Article and Find Full Text PDFTotal Synthesis and Antibacterial Activity of Marine Tris-indole Alkaloid Tulongicin A.
J Nat Prod
June 2024
Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.
Bis-indole alkaloids from marine sponges are an intriguing class of natural products with a variety of activities. However, only a preliminary biological study of tulongicin A (), a related previously isolated marine tris-indole alkaloid, has been conducted. In this study, we accomplished the first asymmetric total synthesis of via the construction of an imidazoline-linked bis-indolylmethane skeleton using a Friedel-Crafts-type reaction.
View Article and Find Full Text PDFTotal Synthesis of the Sesquiterpene (-)-Merrillianin.
Org Lett
April 2024
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
The first total synthesis of (-)-merrillianin (), which is a natural sesquiterpene with a tricyclic structure having a cyclopentane ring and five- and seven-membered lactone parts, is demonstrated. This asymmetric total synthesis enabled the absolute stereostructure determination of naturally occurring (-)-.
View Article and Find Full Text PDFSynthesis of portimines reveals the basis of their anti-cancer activity.
Nature
October 2023
Department of Chemistry, Scripps Research, La Jolla, CA, USA.
Marine-derived cyclic imine toxins, portimine A and portimine B, have attracted attention because of their chemical structure and notable anti-cancer therapeutic potential. However, access to large quantities of these toxins is currently not feasible, and the molecular mechanism underlying their potent activity remains unknown until now. To address this, a scalable and concise synthesis of portimines is presented, which benefits from the logic used in the two-phase terpenoid synthesis along with other tactics such as exploiting ring-chain tautomerization and skeletal reorganization to minimize protecting group chemistry through self-protection.
View Article and Find Full Text PDFThe role of early synthetic materials degradation in the downfall of the Ansaldo A.1, an Italian World War I biplane fighter.
Sci Rep
July 2023
Department of Chemistry and Industrial Chemistry, Via Giuseppe Moruzzi 13, 56124, Pisa, Italy.
From the Pioneer Era of the aviation to World War I the evolution of aircraft technology and chemical synthesis enabled a unique coexistence of traditional craftsmanship, artistic decoration practices, and technological advancements. The study of the materials used in these early years of aviation is still an uncharted territory: a vast portion of remaining planes has been partially or completely repaired and restored, usually by total replacement of the fabric. The Italian biplane Ansaldo A.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!