Parallel synthesis of an imidazole-4,5-dicarboxamide library bearing amino acid esters and alkanamines.
The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters and alkanamines to afford compounds with intramolecularly hydrogen bonded conformations that mimic substituted purines and therefore are hypothesized to be potential inhibitors of kinases through competitive binding to the ATP site. In this work, a total of 126 dissymmetrically disubstituted imidazole-4,5-dicarboxamides with amino acid ester and alkanamide substituents were prepared by parallel synthesis. The library members were purified by column chromatography on silica gel and the purified compounds characterized by LC-MS with LC detection at 214 nm. A selection of the final compounds was also analyzed by (1)H-NMR spectroscopy. The analytically pure final products have been submitted to the Molecular Library Small Molecule Repository (MLSMR) for screening in the Molecular Library Screening Center Network (MLSCN) as part of the NIH Roadmap.
Solinas
Rosanna
R
Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, OK 74104, USA. rosannasolinas@yahoo.it
DiCesare
John C
JC
Baures
Paul W
PW
D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D000620:Aminoimidazole Carboxamide / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011719:Pyrazines / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D000596:Amino Acids; D004952:Esters; D007093:Imidazoles; D011719:Pyrazines; D054852:Small Molecule Libraries; D000620:Aminoimidazole Carboxamide; C029899:imidazole; C031340:imidazolecarboxamide