105259-96-9

Upstream product

• 13404-22-3 tert-butyl L-alaninate hydrochloride 
• 99198-61-5 ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate 
• 105259-95-8 L-alanine tert butyl ester 

Downstream Products

• 773808-70-1 4-[(R)-5-((S)-1-Carboxy-ethylamino)-5-ethoxycarbonyl-pentyl]-piperidine-1-carboxylic acid benzyl ester 
• 105259-81-2 tert-butyl N--L-alanyl>-N-(2-indanyl)glycinate 
• 120008-76-6 4-{(R)-5-[(S)-2-((S)-2-Benzyloxycarbonyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethylamino]-5-ethoxycarbonyl-pentyl}-piperidine-1-carboxylic acid benzyl ester 
• 120008-88-0 (2S,3aS,7aS)-1-{(S)-2-[(R)-5-(1-Benzyloxycarbonyl-piperidin-4-yl)-1-ethoxycarbonyl-pentylamino]-propionyl}-octahydro-indole-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis and angiotensin converting enzyme-inhibitory activity of N- [(1S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanine derivatives

As part of a search for potent and long-lasting angiotensin converting enzyme (ACE) inhibitors, various types of N-[(1S)-1-carboxy-5-(4- piperidyl)pentyl]-L-alanine derivatives (7a, 8-11) were prepared. The key synthetic intermediate, N-[(1S)-5-(1-benzyloxycarbonyl-4-piperidyl)-1- ethoxycarbonylpentyl]-L-alanine (17a), was synthesized by asymmetric reduction of the α-oxoester (13) with Lactobacillus paracasei subsp. paracasei followed by a substitution reaction with tert-butyl L-alanine (15) and subsequent treatment with hydrogen chloride. Compounds 7a and 8-11 showed potent and long-lasting ACE-inhibitory activity in rats.

Synthesis and angiotensin converting enzyme inhibitory activity of N-carboxymethyldipeptides with ω-(4-piperidyl)alkyl group

The synthesis of a series of novel, potent angiotensin converting enzyme (ACE) inhibitors containing 1(S)-carboxy-ω-(4-piperidyl)alkyl group at the N-terminal of the dipeptide is described. These 1-carboxy-ω-(4-piperidyl)alkyl derivatives possess greater or equivalent in vitro potency and in vivo efficacy than captopril and enalapril. The length (n) of the carbon chain in the ω-(4-piperidyl)alkyl moiety was varied from two to six to investigate the optimal structure for long-acting ACE inhibitors. 1-[N-[1(S)-Carboxy-6-(4-piperidyl)hexyl]-L-alanyl]-(2α,3aβ,7aβ)-oct ahydro-1H-indole-2-carboxylic acid, the most potent member of the series, had an in vivo area under the curve (AUC) of 685, which was calculated by the inhibition of angiotensin I-induced pressor response vs. time curves (0 to 8 h) after p.o. administration.

Piperidine derivatives

Novel Compounds of the formula: STR1 [wherein A is an α-amino acid residue; B is a group represented by the formula: STR2 (wherein R4 is hydrogen, lower alkyl, aralkyl or amino-lower alkyl), whereby the linkage between the symbols A and B desig