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Tripodal trisamides based on nicotinic and picolinic acid derivatives

TitleTripodal trisamides based on nicotinic and picolinic acid derivatives
Publication TypeJournal Article
Year of Publication1998
AuthorsHoveyda, HR, Karunaratne, V, Nichols, CJ, Rettig, SJ, Stephens, AKW, Orvig, C
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume76
Pagination414-425
Date PublishedApr
Type of ArticleArticle
ISBN Number0008-4042
Keywordsaluminum, arylamide, CHELATE COMPLEXES, COORDINATION CHEMISTRY, DISTANCES, ENTEROBACTIN ANALOGS, FERRIC ENTEROBACTIN, gallium, hydrogen bonding, MICROBIAL IRON TRANSPORT, NEUTRAL WATER, preorganization, STABILITY
Abstract

{A number of polydentate arylamide ligands have been prepared by coupling various acyclic tripodal or linear polyamines with derivatives of nicotinic and picolinic acids. Two synthetic procedures were utilized; tris {[(2-hydroxynicotinyl)carbonyl]-2-aminoethyl} (H3NICTREN) was prepared by Method A, the HOSu/DCC method, and the other arylamides in this study were prepared by Method B, the CDI method. Method A involved the reaction of N-hydroxysuccinimide with 2-hydroxynicotinic acid (in the presence of dicyclohexylcarbodiimide (DCC) as a dehydrative coupling reagent) to form the succinimide ester, followed by reaction with TREN to yield H3NICTREN. Method B involved reaction of a carboxylic acid (2-hydroxynicotinic, 3-hydroxypicolinic, nicotinic, or picolinic acids) with carbonyldiimidazole (CDI) to form the N-acylimidazolide, followed by reaction with the amine (TREN, TAME, spermidine, or TRPN) to yield the desired arylamide. The X-ray structure of 1,1,1-tris{[(3 -hydroxypicolinyl) carbonyl] -2-aminomethyl} ethane (H3PICTBME) was determined; crystals of H(3)PICTAME are monoclinic

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