858366-85-5

Upstream product

• 73-32-5 L-isoleucine 
• 488-15-3 (2S,3S)-2-Hydroxy-3-methylpentanoic acid 
• 56577-28-7 methyl (2S,3S)-2-hydroxy-3-methylpentanoate 
• 858366-75-3 methyl (2S,3S)-2-(benzyloxy)-3-methylpentanoate 

Downstream Products

• 858366-80-0 (2S,3S)-2-(benzyloxy)-3-methylpentanal 
• 1420778-38-6 methyl 5-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}pentanoate 
• 936712-88-8 methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-4-nitro-5-phenyl-prolylamino}hexanoate 
• 936712-91-3 methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate 
• 936712-94-6 [(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolyl]-β-alanine 
• 936712-97-9 methyl 4-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]butanoate 
• 1420778-40-0 methyl 5-[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolylamino]pentanoate 
• 936712-57-1 5-{(2S,3R,4S,5S)-3-[(2S)-1-(benzyloxy)-2-methylbutyl]-4-nitro-5-phenylpyrrolidine-2-carboxamido}pentanoic acid 
• 1420778-37-5 methyl 5-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-4-nitro-5-phenyl-prolylamino}pentanoate 
• 1207955-33-6 methyl 4-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}butanoate 
• 1420778-36-4 methyl 4-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-4-nitro-5-phenyl-prolylamino}butanoate 
• 936712-85-5 methyl {(2S,3R,4S,5S)-3-[(1S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl}prolyl-β-alaninate 
• 1420778-34-2 methyl {(2S,3R,4S,5S)-3-[(1S)-1-benzyloxy-2-methylbutyl]-4-nitro-5-phenyl}prolyl-β-alaninate 
• 1420778-41-1 6-[(2S,3R,4S,5S)-1-(2-aminoacetyl)-3-[(2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylprolylamino]pentanoic acid 

Relevant academic research and scientific papers

Design, synthesis, and functional evaluation of leukocyte function associated antigen-1 antagonists in early and late stages of cancer development

The integrin leukocyte function associated antigen 1 (LFA-1) binds the intercellular adhesion molecule 1 (ICAM-1) by its αL-chain inserted domain (I-domain). This interaction plays a key role in cancer and other diseases. We report the structure-based design, small-scale synthesis, and biological activity evaluation of a novel family of LFA-1 antagonists. The design led to the synthesis of a family of highly substituted homochiral pyrrolidines with antiproliferative and antimetastatic activity in a murine model of colon carcinoma, as well as potent antiadhesive properties in several cancer cell lines in the low micromolar range. NMR analysis of their binding to the isolated I-domain shows that they bind to the I-domain allosteric site (IDAS), the binding site of other allosteric LFA-1 inhibitors. These results provide evidence of the potential therapeutic value of a new set of LFA-1 inhibitors, whose further development is facilitated by a synthetic strategy that is versatile and fully stereocontrolled.

Application of stereocontrolled stepwise [3+2] cycloadditions to the preparation of inhibitors of α4β1-integrin- mediated hepatic melanoma metastasis

(Chemical Equation Presented) Inhibitors of the interaction between protein VLA-4 and its natural ligand VCAM-1 have been designed, even though the structure of the protein remains unresolved. The rational design relied on the simulation of the steric and electronic properties of the active loop of VCAM-1, whose structure is known (see picture), and the inhibitors were readily prepared by stereoselective stepwise [3+2] cycloadditions.