Synthesis and Structure-Activity Relationship Studies of C(13)-Desmethylene-(-)-Zampanolide Analogs.
medicinal chemistry
natural products
structure-activity relationships
total synthesis
zampanolide
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
27 Jun 2023
27 Jun 2023
Historique:
received:
04
03
2023
medline:
30
6
2023
pubmed:
15
4
2023
entrez:
14
4
2023
Statut:
ppublish
Résumé
We describe the synthesis and biochemical and cellular profiling of five partially reduced or demethylated analogs of the marine macrolide (-)-zampanolide (ZMP). These analogs were derived from 13-desmethylene-(-)-zampanolide (DM-ZMP), which is an equally potent cancer cell growth inhibitor as ZMP. Key steps in the synthesis of all compounds were the formation of the dioxabicyclo[15.3.1]heneicosane core by an intramolecular HWE reaction (67-95 % yield) and a stereoselective aza-aldol reaction with an (S)-BINOL-derived sorbamide transfer complex, to establish the C(20) stereocenter (24-71 % yield). As the sole exception, for the 5-desmethyl macrocycle, ring-closure relied on macrolactonization; however, elaboration of the macrocyclization product into the corresponding zampanolide analog was unsuccessful. All modifications led to reduced cellular activity and lowered microtubule-binding affinity compared to DM-ZMP, albeit to a different extent. For compounds incorporating the reactive enone moiety of ZMP, IC
Identifiants
pubmed: 37057902
doi: 10.1002/chem.202300703
doi:
Substances chimiques
zampanolide
0
Macrolides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300703Subventions
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : 200021_149253)
Organisme : Eidgenössische Technische Hochschule Zürich
ID : Insitutional fundig
Organisme : Ministerio de Ciencia e Innovación
ID : PID2019-104545RBI00 /AEI/10.13039/501100011033
Organisme : European Commission-NextGenerationsEU
ID : Regulation EU 2020/2094
Organisme : Fundación Tatiana Pérez de Guzmán el Bueno
Organisme : Victoria University Strategic Investment Fund
Organisme : Cancer Society of New Zealand
Organisme : Wellington Medical Research Foundation
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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