Synthesis of novel keto-ACE analogues as domain-selective angiotensin I-converting enzyme inhibitors

Aloysius T Nchinda; Kelly Chibale; Pierre Redelinghuys; Edward D Sturrock

doi:10.1016/j.bmcl.2006.06.003

Synthesis of novel keto-ACE analogues as domain-selective angiotensin I-converting enzyme inhibitors

Bioorg Med Chem Lett. 2006 Sep 1;16(17):4612-5. doi: 10.1016/j.bmcl.2006.06.003. Epub 2006 Jun 19.

Authors

Aloysius T Nchinda¹, Kelly Chibale, Pierre Redelinghuys, Edward D Sturrock

Affiliation

¹ Institute of Infectious Disease and Molecular Medicine, University of Cape Town, Observatory 7925, South Africa.

PMID: 16784850
DOI: 10.1016/j.bmcl.2006.06.003

Abstract

Novel analogues of the angiotensin I-converting enzyme (ACE) inhibitor keto-ACE were synthesized via a facile Horner-Emmons olefination of a phosphonoketone precursor with ethyl glyoxylate. Introduction of a bulky aromatic tryptophan at the P(2)(') position of keto-ACE resulted in a significant increase in C-domain-selectivity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Angiotensin-Converting Enzyme Inhibitors / chemical synthesis*
Angiotensin-Converting Enzyme Inhibitors / chemistry
Angiotensin-Converting Enzyme Inhibitors / pharmacology*
Molecular Structure
Peptidyl-Dipeptidase A / metabolism*
Structure-Activity Relationship

Substances

Angiotensin-Converting Enzyme Inhibitors
Peptidyl-Dipeptidase A