247202-80-8

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 3017-32-1 (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate 
• 370108-19-3 (S)-6-tert-Butoxycarbonylamino-2-[(E)-3-(4-nitro-phenyl)-allylamino]-hexanoic acid methyl ester 

Downstream Products

• 247203-80-1 2-[bis-(4-benzyloxy-benzyl)-amino]-6-tert-butoxycarbonylamino-hexanoic acid methyl ester 

Relevant academic research and scientific papers

Compounds and compositions for treating obesity

Described herein are novel and useful compounds of the general formula Compounds of this invention can advantageously exhibit melanocortin receptor agonist activity. New and useful compounds comprising such a chemical structure and methods of modulating melanocortin receptor activity in a subject (and promoting, inducing, and/or enhancing the treatment or prevention of related diseases) by administering such a compound or composition also are described.

COMPOUNDS FOR USE IN TREATING OBESITY

The present invention relates to novel compounds of the general formula (I) as well as any optical or geometric isomer or tautomer form thereof, or a pharmaceutically acceptable salt thereof, as agonists of melanocortin receptors, such as agonists of the MC4 receptor. The compounds may for instance be used in the treatment of obesity.

Solid-phase synthesis of N(α)-benzyl-N(α)-cinnamyl lysine and glutamic acid derivatives

Several variations of a solid-phase strategy for the synthesis of N(α)- benzyl-N(α)-cinnamyl lysine and glutamic acid derivatives are presented. Starting from the corresponding N(α)-Fmoc amino acids on Wang resin, reductive alkylation using nitrocinnamaldehyde or a substituted benzaldehyde was followed by nucleophilic displacement of a substituted benzyl halide or nitrocinnamyl bromide to provide resin-bound intermediates. Diversity was added by reduction of the nitro group and derivatization of the resulting aminocinnamyl moiety with a variety of acylating or sulfonylating reagents. Using an orthogonal protecting group strategy, N(ε)-Dde-protected lysine derivatives were further functionalized at the side-chain amino group prior to cleavage from resin. This method allows for the preparation of analog libraries having up to four points of diversity. (C) 2000 Elsevier Science Ltd.

Synthesis and erythropoietin receptor binding affinities of N, N-disubstituted amino acids

N,N-Dicinnamyl, N-benzyl-N-cinnamyl, and N,N-dibenzyl amino acids were prepared and evaluated in an EPO binding assay. Several derivatives of aspartic acid, glutamic acid, and lysine exhibited moderate (10-50 μM) affinity for EBP; 'dimerization' of the most potent analogues by coupling with linear diamines led to EPO competitors having 1-2 μM binding affinities. (C) 2000 Elsevier Science Ltd.