169701-40-0

Upstream product

• 21685-51-8 D-phenylalanine methyl ester 
• 598-21-0 2-Bromoacetyl bromide 
• 673-06-3 D-(R)-phenylalanine 
• 79-08-3 bromoacetic acid 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 

Downstream Products

• 556068-61-2 methyl (3R)-3-[(2-{[(1R)-1-benzyl-2-methoxy-2-oxoethyl]amino}-2-oxoethyl)amino]dodecanoate 
• 556068-60-1 methyl (3S)-3-[(2-{[(1R)-1-benzyl-2-methoxy-2-oxoethyl]amino}-2-oxoethyl)amino]dodecanoate 
• 556068-65-6 methyl (3R)-3-[(3R)-3-benzyl-2,5-dioxopiperazinyl]dodecanoate 
• 556068-64-5 methyl (3S)-3-[(3R)-3-benzyl-2,5-dioxopiperazinyl]dodecanoate 
• 1379456-33-3 Br^(1-)*C₁₆H₂₀N₃O₃⁽¹⁺⁾ 

Relevant academic research and scientific papers

Antimicrobial toxicity studies of ionic liquids leading to a 'hit' MRSA selective antibacterial imidazolium salt

Imidazolium salts can be classed as surfactants, detergents, ionic liquids, reagents, catalysts or solvents. A study of the toxicity and ecotoxicity of these salts yields valuable information for their use as pharmaceuticals as well as impact on the environment. Our approach to screen a series of chiral imidazolium salts for toxicity to bacteria and fungi, including clinical pathogen strains, has led to the identification of a 'hit' MRSA selective antimicrobial compound. Preliminary structure-activity-relationship (SAR) information (required position of l-phenylalanine and l-valine group) is also elucidated within this first generation of compounds. Conversely, most of the imidazolium salts were nontoxic (IC95 > 2 mM) to the 12 fungi strains and 8 bacteria strains screened, and we propose that they are suitable candidates for 'green chemistry' applications. Ecotoxicity studies (Biodegradation ISO 14593 'CO2 Headspace Test') of two bromide ionic liquids containing l-phenylalanine residues indicate that these ionic liquids passed the test (>60% in 28 days) and classed as readily biodegradable.

1,2,3-TRIAZOLE-BASED PEPTIDOMIMETIC INTEGRIN INHIBITORS FOR THE DIAGNOSIS AND THERAPY OF TUMORS

The present invention refers to the field of chemical compounds bearing a 1,2,3-triazole ring of formula (I) and possessing guanidino and carboxylic groups or their isosteres, their preparation by Cu-catalyzed "click-chemistry", and medical - diagnostic use in pathologies where angiogenesis is altered, for example pathologic conditions of tumor origin, tumor metastasis, osteoporosis, and rheumatoid arthritis.

Click-chemistry-derived triazole ligands of arginine-glycine-aspartate (RGD) integrins with a broad capacity to inhibit adhesion of melanoma cells and both in vitro and in vivo angiogenesis

A click chemistry approach was applied for the discovery of triazole-based arginine-glycine-aspartate (RGD) mimetics by Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction, which showed binding affinity properties toward αvβ3/αvβ5 integrins. Biological assays showed compound 18 capable of binding αvβ3 integrin with nanomolar affinity according to a two-sites model, and molecular modeling studies revealed a peculiar π-stacking interaction between the triazole ring and Tyr178 side chain. Accordingly, compound 18 inhibited the adhesion of integrin-expressing human melanoma cells to RGD-containing proteins of the extracellular matrix, such as vitronectin, fibronectin, and osteopontin, and also angiogenesis in in vitro and in vivo experimental models. The relevant biological effects exerted by compound 18 suggest its potential application as an antiangiogenic agent in the diagnosis and therapy of tumors where αvβ3 integrin expression is up-regulated.

Determination of the absolute stereochemistry of Etzionin

The absolute configuration of Etzionin, a marine peptide-like compound isolated in 1989 from a red tunicate collected from the Red Sea has been determined by a combination of synthetic and spectroscopic procedures. Finally, its absolute stereochemistry ha

Synthesis of Xaa-Gly-Xaa' Keto-Methylene Tri-peptide Isosteres Incorporating Phenylalanine, Tyrosine and Valine Units.

The utility of amino-acid derived β-ketosulfones in the synthesis of keto-methylene tri-peptide isosteres Xaa-Gly-Xaa', incorporating phenylalanine, tyrosine and valine units is reported.Both L,L andL,D forms of the tripeptide systems have been prepared using this methodology.