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

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 increa...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2006-09, Vol.16 (17), p.4612-4615
Hauptverfasser:	Nchinda, Aloysius T., Chibale, Kelly, Redelinghuys, Pierre, Sturrock, Edward D.
Format:	Artikel
Sprache:	eng
Schlagworte:	ACE inhibitor Angiotensin-Converting Enzyme Inhibitors - chemical synthesis Angiotensin-Converting Enzyme Inhibitors - chemistry Angiotensin-Converting Enzyme Inhibitors - pharmacology Antihypertensive agents Biological and medical sciences Cardiovascular system Horner–Emmons Keto-ACE Medical sciences Molecular Structure Olefination Peptidyl-Dipeptidase A - metabolism Pharmacology. Drug treatments Structure-Activity Relationship
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Beschreibung
Zusammenfassung:	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.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2006.06.003