A1 Refereed original research article in a scientific journal
Solid-Phase Synthesis of 4(5),1 ',5 '-Trisubstituted 2,4 '-Biimidazoles
Authors: Karskela T, Lonnberg H
Publisher: AMER CHEMICAL SOC
Publication year: 2009
Journal:: Journal of Organic Chemistry
Journal name in source: JOURNAL OF ORGANIC CHEMISTRY
Journal acronym: J ORG CHEM
Volume: 74
Issue: 24
First page : 9446
Last page: 9451
Number of pages: 6
ISSN: 0022-3263
DOI: https://doi.org/10.1021/jo902122e
Abstract
A method for the synthesis of libraries of 4(5), 1',5'-tri substituted 2,4'-biimidazoles on a solid support was developed.(1) A trivalent scaffold, 2-(5'-amino-4(5)-formyl-1H,1'H-2,4'-biimidazol-1'-yl)acetic acid, was first prepared in solution by a two-step synthesis from ethyl adenin-9-ylacetate and bromomalonaldehyde. The product was coupled to an amino acid loaded Wang resin and the formyl group was subsequently derivatized either by reductive amination, oximation, or hydrazone formation. The 5'-amino group of the resin-bound biimidazole was then acylated and the products were finally released from the resin and purified. 5'-Amino-2,4'-biimidazole offers a scaffold for lead compounds of drug discovery, possibly useful in finding leads for protein kinase inhibitors.
A method for the synthesis of libraries of 4(5), 1',5'-tri substituted 2,4'-biimidazoles on a solid support was developed.(1) A trivalent scaffold, 2-(5'-amino-4(5)-formyl-1H,1'H-2,4'-biimidazol-1'-yl)acetic acid, was first prepared in solution by a two-step synthesis from ethyl adenin-9-ylacetate and bromomalonaldehyde. The product was coupled to an amino acid loaded Wang resin and the formyl group was subsequently derivatized either by reductive amination, oximation, or hydrazone formation. The 5'-amino group of the resin-bound biimidazole was then acylated and the products were finally released from the resin and purified. 5'-Amino-2,4'-biimidazole offers a scaffold for lead compounds of drug discovery, possibly useful in finding leads for protein kinase inhibitors.
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