A1 Refereed original research article in a scientific journal

Polyazacyclophanes incorporating two pyridine units and a heteroaromatic pendant group as potential cleaving agents of mRNA F '-cap structure




AuthorsZhang ZB, Mikkola S, Lonnberg H

PublisherVERLAG HELVETICA CHIMICA ACTA AG

Publication year2005

JournalChemistry and Biodiversity

Journal name in sourceCHEMISTRY & BIODIVERSITY

Journal acronymCHEM BIODIVERS

Volume2

Issue8

First page 1116

Last page1126

Number of pages11

ISSN1612-1872

DOIhttps://doi.org/10.1002/cbdv.200590081(external)


Abstract
Four hexaazacyclophanes, 16a-d, incorporating two pyridine units and a (pyridin-2-yl)methyl or (quinolin2-yl)methyl pendant group at one of the ring N-atoms have been prepared. The key step of the synthesis is an intermolecular cyclization of N,N-bis{[6-(tosyloxymethyl)pyridin-2-yl]methyl}-2-nitrobenzenesulfonamide (7) with either tert-butyl bis{2-[(2-nitrophenylsulfonyl)amino]ethyl}carbamate (2a) or tert-butyl bis[3-[(2-nitro-phenylsulfonyl)amino]propyl]carbamate (2b) in the presence of anhydrous CS2CO3. Removal of the acid-labile tert-butoxycarbonyl protection then allows attachment of the pendant group by reductive alkylation to the exposed secondary amino group, and deprotection of the remaining aliphatic ring N-atoms completes the synthesis. The ability of the cyclophanes and their dinuclear Cu2+ and Zn1+ complexes to cleave the mRNA cap structure, m(7)G(5 ')pppG(5 ') (1), has been studied.


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