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Azumamides A-E: Isolation, Synthesis, Biological Activity, and Structure-Activity Relationship.
Molecules
December 2022
College of Pharmacy, Korea University, Sejong 30019, Republic of Korea.
Cyclic peptides are one of the important chemical groups in the HDAC inhibitor family. Following the success of romidepsin in the clinic, naturally occurring cyclic peptides with a hydrophilic moiety have been intensively studied to test their function as HDAC inhibitors. Azumamides A-E, isolated from , are one of the powerful HDAC inhibitor classes.
View Article and Find Full Text PDFTotal synthesis and full histone deacetylase inhibitory profiling of Azumamides A-E as well as β²- epi-Azumamide E and β³-epi-Azumamide E.
J Med Chem
August 2013
Department of Chemistry, Technical University of Denmark, Kemitorvet 207, Kongens Lyngby DK-2800, Denmark.
Cyclic tetrapeptide and depsipeptide natural products have proven useful as biological probes and drug candidates due to their potent activities as histone deacetylase (HDAC) inhibitors. Here, we present the syntheses of a class of cyclic tetrapeptide HDAC inhibitors, the azumamides, by a concise route in which the key step in preparation of the noncanonical disubstituted β-amino acid building block was an Ellman-type Mannich reaction. By tweaking the reaction conditions during this transformation, we gained access to the natural products as well as two epimeric homologues.
View Article and Find Full Text PDFAzumamides A-E: histone deacetylase inhibitory cyclic tetrapeptides from the marine sponge Mycale izuensis.
Angew Chem Int Ed Engl
November 2006
Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
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