60939-22-2

Upstream product

• 1629-58-9 4-penten-3-one 
• 103-49-1 dibenzylamine 

Downstream Products

• 252353-76-7 C₄₁H₇₁N₇O₉ 
• 252353-72-3 {4-[benzyl-(3-tert-butoxycarbonylamino-pentyl)-amino]-butylcarbamoyloxy}-acetic acid 
• 252353-66-5 {4-[benzyl-(3-tert-butoxycarbonylamino-pentyl)-amino]-butylcarbamoyloxy}-acetic acid methyl ester 
• 177550-51-5 {3-[(4-amino-butyl)-benzyl-amino]-1-ethyl-propyl}-carbamic acid tert-butyl ester 
• 177550-50-4 {3-[benzyl-(3-cyano-propyl)-amino]-1-ethyl-propyl}-carbamic acid tert-butyl ester 
• 177550-48-0 methanesulfonic acid 3-[benzyl-(3-cyano-propyl)-amino]-1-ethyl-propyl ester 
• 177550-49-1 4-[(3-azido-pentyl)-benzyl-amino]-butyronitrile 
• 252353-58-5 4-[benzyl-(3-hydroxy-pentyl)-amino]-butyronitrile 
• 252353-57-4 1-benzylamino-pentan-3-ol 
• 252353-56-3 1-dibenzylamino-pentan-3-ol 

Relevant academic research and scientific papers

Understanding water mediated proton migration in conversion of π-bond in olefinic carbon atoms into C–N bond to form β-amino adducts

The aza-Michael reactions with a variety of substrates were conducted in water affording the quantitative yields without any external catalyst, which is contrary to that published in literature. A more rational approach to analyze this problem was by conducting this conspicuous reaction with a variety of substrates in water and the results were analyzed using advanced theoretical calculations. Our investigation on the role of water in the reaction proposed a mechanism wherein water plays dual role both as medium as well as catalyst to facilitate the C–N bond formation using powerful tool in its armory, the “H-bonding”. Reactions were conducted in the absence of an external catalyst or co-solvents and, hence, are a greener approach in organic synthesis. The reactions of 15 examples were conducted with a variety of substrates to afford the addition products in the range of 70–95% yield. Theoretical studies on the transition state analysis suggested that it was the assistance of water, through H-bonding, that facilitated the conjugate addition of amine and proton transfer from ammonium ion, which could happen through two equally possible pathways.

Structure - Immunosuppressive activity relationships of new analogues of 15-deoxyspergualin. 2. Structural modifications of the spermidine moiety

A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine 'D' region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene α to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60c which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

Oxy-alkylamino carboxylic esters

Compounds of formula (I): STR1 wherein: X is CO, protected CO, CROH in which R is hydrogen or C1-4 alkyl and in which the OH moiety may be protected; Y is CH2 CH2 or CH=CH; Z is CO or CH2 ; n is 1 to 8; m is 1,