Synthesis of highly functionalized oligobenzamide proteomimetic foldamers by late stage introduction of sensitive groups

Abstract

New routes are developed to allow introduction of sensitive side-chains and synthesis of challenging proteomimetic sequences.

Hypoxia inducible factor (HIF) as a model for studying inhibition of protein–protein interactions

“… 126 Subsequently our group applied this approach to the design of dimeric 3- O -alkylated aromatic oligoamide mimetics of the helix 2 sequence ( Fig. 9a ), 127 however these compounds did not act as inhibitors in fluorescence competition anisotropy assays.…”

A catalytic protein–proteomimetic complex: using aromatic oligoamide foldamers as activators of RNase S

“…The assay relies upon binding of ethidium bromide to unhydrolysed RNA 48. Using the remaining fluorescence as an approximation of activity, we used the assay to screen libraries of previously prepared aromatic oligoamide helix-mimetics (see ESI for structures; ESI Tables S1 and S2†) derived from O -alkylated,44,49,50 N -alkylated14 and hybrid scaffolds,43,51 for reactivation of the S-protein (ESI Fig. S1†).…”

High yield synthesis of trans-azoxybenzene versus 2-isopropoxy-4-nitrobenzoic acid: influence of temperature and base concentration

“…Two more synthetic protocols to prepare 1 have been reported in the literature posterior to Adler's work. 6,26,27 These three-steps syntheses consist in the protection of 2-hydroxy-4-nitrobenzoic acid as methyl ester followed by alkylation of the 2-OH group with 2-propanol under Mitsunobu conditions 26 or with 2bromopropane in the presence of base (e.g. K2CO3).…”

“…K2CO3). 27 Then, the methyl ester is hydrolysed with aqueous NaOH working at room temperature or 65 C to give the desired product 1 with 63% and 82% overall yields, respectively. These synthetic protocols, which use lower temperature for the hydrolysis step with aqueous NaOH, are consistent with our own observations.…”