1608150-75-9

Upstream product

• 1366595-48-3 C₁₈H₂₂N₂O₄ 
• 851544-48-4 (3aS,5R,7aS,9aS)-3-benzyl-4-oxo-decahydro-2-oxa-3,4a-diazacyclopenta[f]azulene-5-carboxylic acid tert-butyl ester 
• 1608150-79-3 (3S,6S,7R,9aS)-methyl 7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 
• 1412423-52-9 (3S,6S,7R,9aS)-methyl 6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-7-(cyanomethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 
• 1412423-66-5 (3S,6S,7R,9aS)-methyl 6-((tert-butoxycarbonyl)amino)-7-(cyanomethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 
• 1099616-09-7 C₁₉H₂₄N₂O₄ 
• 1366595-89-2 C₁₂H₂₀N₂O₄ 

Downstream Products

• 1608150-80-6 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tertbutoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoic acid 
• 1608150-84-0 methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((S)-2-(methylamino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate hydrochloride 
• 1608150-83-9 methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate 

Relevant academic research and scientific papers

Dual action Smac mimetics–zinc chelators as pro-apoptotic antitumoral agents

Dual action compounds (DACs) based on 4-substituted aza-bicyclo[5.3.0]decane Smac mimetic scaffolds (ABDs) linked to a Zn2+-chelating moiety (DPA, o-hydroxy, m-allyl, N-acyl (E)-phenylhydrazone) through their 10 position are reported and characterized. Their synthesis, their target affinity (XIAP BIR3, Zn2+) in cell-free assays, their pro-apoptotic effects and cytotoxicity in tumor cells with varying sensitivity to Smac mimetics are described. The results are interpreted to evaluate the influence of Zn2+chelators on cell-free potency and on cellular permeability of DACs, and to propose novel avenues towards more potent antitumoral DACs based on Smac mimetics and Zn2+chelation.

Synthesis and biological evaluation of dual action cyclo-RGD/SMAC mimetic conjugates targeting αvβ3/α vβ5 integrins and IAP proteins

The rational design, synthesis and in vitro biological evaluation of dual action conjugates 11-13, containing a tumour targeting, integrin αvβ3/αvβ5 ligand portion and a pro-apoptotic SMAC mimetic portion (cyclo-RGD/SMAC mimetic conjugates) are reported. The binding strength of the two separate units is generally maintained by these dual action conjugates. In particular, the connection between the separate units (anchor points on each unit; nature, length and stability of the linker) influences the activity of each portion against its molecular targets (integrins αvβ3/ αvβ5 for cyclo-RGD, IAP proteins for SMAC mimetics). Each conjugate portion tolerates different substitutions while preserving the binding affinity for each target.