74075-31-3

Upstream product

• 83646-23-5 2-((S)-1-Benzyl-2-oxo-hex-5-enyl)-isoindole-1,3-dione 
• 74075-27-7 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<(1S)-1-phthalimido-2-phenylethyl>-1,3-dioxolane 
• 74075-26-6 2-(3-oxo-5-phenyl-(4S)-4-phthalimidopentyl)-1,3-dioxolane 
• 74075-29-9 2-<2-(1,3-dioxolan-2-yl)ethyl>-2-<(1S)-1-benzamido-2-phenylethyl>-1,3-dioxolane 
• 74075-28-8 (S)-1-[2-(2-[1,3]Dioxolan-2-yl-ethyl)-[1,3]dioxolan-2-yl]-2-phenyl-ethylamine 
• 33861-65-3 N-phthaloyl-L-phenylalanine-2-mercaptopyridyl thioester 
• 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 
• 83646-28-0 N-[(S)-1-(2-But-3-enyl-[1,3]dioxolan-2-yl)-2-phenyl-ethyl]-benzamide 

Downstream Products

• 96792-07-3 N-<5(S)-benzamido-4-oxo-6-phenylhexanoyl>-2-(diethoxyphosphinyl)pyrrolidine 
• 74075-32-4 (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenyl-hexanoyl-L-proline benzyl ester 
• 910316-87-9 (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenyl-hexanoyl-L-phenylalanine methyl ester 
• 910316-85-7 (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenyl-hexanoyl-L-tryptophan methyl ester 
• 96792-02-8 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-proline hydroxylamide 
• 96792-01-7 N-<5(S)-benzamido-4-oxo-6-phenylhexanoyl>-2-phosphonopyrrolidine 
• 77921-67-6 (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenylhexanoyl-L-phenylalanine 
• 74075-33-5 SRI-20 
• 96792-03-9 5-<1-<5(S)-benzamido-4-oxo-6-phenylhexanoyl>pyrrolidin-2-yl>tetrazole 
• 96792-05-1 succinimidyl 5(S)-benzamido-4-oxo-6-phenylhexanoate 

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 OF KETOMETHYLENE ANALOGS OF DIPEPTIDES

A convenient method of synthesizing ketomethylene dipeptides by using homoallylic Grignard reagents as amino acid analog synthons is described.

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.