74075-33-5

Usage

InChI:InChI=1/C24H26N2O5/c27-21(13-14-22(28)26-15-7-12-20(26)24(30)31)19(16-17-8-3-1-4-9-17)25-23(29)18-10-5-2-6-11-18/h1-6,8-11,19-20H,7,12-16H2,(H,25,29)(H,30,31)/t19-,20-/m0/s1

Upstream product

• 74075-32-4 (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenyl-hexanoyl-L-proline benzyl ester 
• 74075-27-7 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<(1S)-1-phthalimido-2-phenylethyl>-1,3-dioxolane 
• 74075-29-9 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<(1S)-1-benzamido-2-phenylethyl>-1,3-dioxolane 
• 33861-65-3 N-phthaloyl-L-phenylalanine-2-mercaptopyridyl thioester 
• 74075-31-3 (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenyl-hexanoic acid 
• 68709-76-2 5(S)-<(butyloxycarbonyl)amino>-6-phenyl-4-oxohexanoic acid 
• 910316-84-6 (5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoyl-L-proline benzyl ester 
• 910316-83-5 ethyl (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenyl-hexanoate 
• 74075-30-2 3-[2-((S)-1-Benzoylamino-2-phenyl-ethyl)-[1,3]dioxolan-2-yl]-propionic acid 
• 74075-28-8 (S)-1-[2-(2-[1,3]Dioxolan-2-yl-ethyl)-[1,3]dioxolan-2-yl]-2-phenyl-ethylamine 
• 74075-26-6 2-(3-oxo-5-phenyl-(4S)-4-phthalimidopentyl)-1,3-dioxolane 
• 68709-74-0 ethyl (5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-hexanoate 

Downstream Products

• 77921-47-2 (S)-1-<5-(benzoylamino)-4-(hydroxyimino)-1-oxo-6-phenylhexyl>-L-proline 

Relevant academic research and scientific papers

Angiotensin I-converting enzyme (ace) inhibitors

This invention relates to a process for the synthesis of ketomethylene derivatives of the tripeptide Phe-Gly-Pro (“keto-ACE”, compound 5a) and analogues thereof. The synthesis process proceeds via an α,β-unsaturated keto intermediate. A key feature of the process involves a Horner-Emmons olefination of the, -unsaturated keto-phosphonate with ethyl glyoxylate. Keto-ACE analogues produced by the process of the invention display C-domain selectivity.

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 P2

Synthesis and biological activity of a ketomethylene analogue of a tripeptide inhibitor of angiotensin converting enzyme

An analogue of a tripeptide inhibitor of angiotensin converting enzyme, Bz-Phe-Gly-Pro, has been synthesized in which the amide bond connecting phenylalanine and glycine has been replaced by a ketomethylene group. This nonpeptide analogue, 20, shows more potent converting enzyme inhibiting activity, I50=0.07 μM, than Bz-Phe-Gly-Pro, I50=9.4 μM, or than the orally active D-3-mercapto-2-methylpropanoyl-L-proline (captopril, 1)I50=0.30 μM. Compound 20 has a K(i)of 1.06 x 10-7 and either competitive or noncompetitive enzyme kinetics depending on what substrate is used in the converting enzyme assay. In tests for inhibition of angiotensin I induced contractions in the guinea pig ileum, 20 has one-tenth the activity of 1.