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Literature DB >> 21607116

Structure-activity relationships of ustiloxin analogues.

Madeleine M Joullié¹, Simon Berritt, Ernest Hamel.

Abstract

Four novel ustiloxin D analogues were synthesized focusing on the size of the macrocyclic core, the stereochemistry at the bridgehead ether, and the enantiomer of ustiloxin D. All four were subjected to biological evaluation testing the inhibition of tubulin polymerization. Only 2,2-dimethyl-ustiloxin D retained any activity.

Entities: Chemical Disease Species

Year: 2011 PMID： 21607116 PMCID： PMC3098461 DOI： 10.1016/j.tetlet.2010.11.165

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

12 in total

Review 1. Antimitotic peptides and depsipeptides.

Authors: Ernest Hamel; David G Covell
Journal: Curr Med Chem Anticancer Agents Date: 2002-01

2. Enantioselective total synthesis of ustiloxin D.

Authors: Hiroko Tanaka; Andrew M Sawayama; Thomas J Wandless
Journal: J Am Chem Soc Date: 2003-06-11 Impact factor: 15.419

3. A convergent total synthesis of ustiloxin D via an unprecedented copper-catalyzed ethynyl aziridine ring-opening by phenol derivatives.

Authors: Pixu Li; Cory D Evans; Madeleine M Joullié
Journal: Org Lett Date: 2005-11-10 Impact factor: 6.005

4. Structural insight into the inhibition of tubulin by vinca domain peptide ligands.

Authors: Anthony Cormier; Matthieu Marchand; Raimond B G Ravelli; Marcel Knossow; Benoît Gigant
Journal: EMBO Rep Date: 2008-09-12 Impact factor: 8.807

Review 5. Antimitotic natural products and their interactions with tubulin.

Authors: E Hamel
Journal: Med Res Rev Date: 1996-03 Impact factor: 12.944

6. Total synthesis and biological evaluation of ustiloxin natural products and two analogs.

Authors: Pixu Li; Cory D Evans; Erin M Forbeck; Haengsoon Park; Ruoli Bai; Ernest Hamel; M M Joullié
Journal: Bioorg Med Chem Lett Date: 2006-07-11 Impact factor: 2.823

7. Chiral Salen-Aluminum Complexes as Catalysts for Enantioselective Aldol Reactions of Aldehydes and 5-Alkoxyoxazoles: An Efficient Approach to the Asymmetric Synthesis of syn and anti beta-Hydroxy-alpha-amino Acid Derivatives Financial support has been provided by the National Institutes of Health (GM 43912-11 and GM 33328-18).

Authors: David A. Evans; Jacob M. Janey; Nabi Magomedov; Jason S. Tedrow
Journal: Angew Chem Int Ed Engl Date: 2001-05-18 Impact factor: 15.336

Structure-activity relationships of ustiloxin analogues.

Review 1. Antimitotic peptides and depsipeptides.

2. Enantioselective total synthesis of ustiloxin D.

3. A convergent total synthesis of ustiloxin D via an unprecedented copper-catalyzed ethynyl aziridine ring-opening by phenol derivatives.

4. Structural insight into the inhibition of tubulin by vinca domain peptide ligands.

Review 5. Antimitotic natural products and their interactions with tubulin.

6. Total synthesis and biological evaluation of ustiloxin natural products and two analogs.

8. Total synthesis of ustiloxin D and considerations on the origin of selectivity of the asymmetric allylic alkylation.

9. A regio- and stereoselective approach to quaternary centers from chiral trisubstituted aziridines.

10. Evolution of the total syntheses of ustiloxin natural products and their analogues.

1. Synthesis and Structure-Activity Relationship Study of 1-Phenyl-1-(quinazolin-4-yl)ethanols as Anticancer Agents.

2. Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy.