Parallel Synthesis of An Oligomeric Imidazole-4,5-dicarboxamide Library

Abstract

A library of oligomeric compounds was synthesized based on the imidazole-4,5-dicarboxylic acid scaffold along with amino acid esters and chiral diamines derived from amino acids. The final compounds incorporate non-polar amino acids (Leu, Phe, Trp), polar amino acids (Ser, Asp, Arg), and neutral amino acids (Gly, Ala), and where designed to be useful in screening for inhibitors of protein-protein interactions. Many of the protected and deprotected oligomers show evidence of conformational isomers persistent at room temperature in aqueous solution. A total of 317 final oligomers, out of 441 targeted compounds, were obtained in high analytical purity and of sufficient quantity in order to submit them for high-throughput screening as part of the NIH Roadmap.

Syntheses, structures and properties of four metal-organic frameworks from chlorophenyl imidazole dicarboxylates

“…In this context, the N-heterocyclic dicarboxylate ligands have been widely used to construct MOFs owing to various coordination modes, such as monodentate, bidentate chelating, monodentate and bidentate bridging [14][15][16][17]. Imidazole-4,5-dicarboxylic acid (H 3 IDC) having the above mentioned advantages has been explored to assemble MOFs [18][19][20][21][22][23], possessing six potential oxygen and nitrogen donors. Different substituents have also been introduced into the 2-position of H 3 IDC, such as ethyl, propyl, phenyl, hydroxymethyl, or pyridyl groups [24][25][26][27][28].…”

Copper(I)‐Mediated Denitrogenative Macrocyclization for the Synthesis of Cyclic α3β‐Tetrapeptide Analogues

“…The combined organic layers were dried over MgSO 4 ,f iltered, and concentrated under re-duced pressure to afford the crude product. The crude residue was purified by column chromatography on silica gel by using 20 % ethyl acetate in hexane as as olvent system to afford the desired product (4) Synthesis of 5 [38] Potassium carbonate (3160 mg, 22.84 mmol) was added to astirred solution of 1 (2000 mg, 11.42 mmol) in DMF (18 mL). As olution of iodomethane (6480 mg, 45.69 mmol) in DMF (20 mL) was added dropwise by means of an addition funnel.…”

Synthesis of novel cyclopeptides containing heterocyclic skeletons

“…84,85 Meanwhile, many reports investigated the importance of the imidazole-4,5-dicarboxylic acid scaffold in drug discovery. [86][87][88][89] To extend the library of peptide-macrocycles that contain imidazole-4,5-dicarboxylic acid, Baures and co-workers designed and synthesized a unique novel compound class inspired by macrocyclic natural products. The synthesized compounds are 14-membered macrocycles with differences in their stereochemistry and amino acid side chains.…”