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



: Zhang ZB, Mikkola S, Lonnberg H

Publisher: VERLAG HELVETICA CHIMICA ACTA AG

: 2005

: Chemistry and Biodiversity

: CHEMISTRY & BIODIVERSITY

: CHEM BIODIVERS

: 2

: 8

: 1116

: 1126

: 11

: 1612-1872

DOI: https://doi.org/10.1002/cbdv.200590081(external)


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.



Last updated on 2024-26-11 at 10:23