Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes

• Krzysztof M. Zwoliński and
• Julita Eilmes

Beilstein J. Org. Chem. 2019, 15, 617–622, doi:10.3762/bjoc.15.57

• , were synthesized in satisfactory 26–28% isolated yields. Direct N-alkylation of 1,4,10-trioxa-7,13-diazacyclopentadecane by symmetric DBTAA derivatives bearing bromoalkoxy pendants proceed smoothly at a reasonable level of dilution (1.25 mM). The structures were fully characterized by HR-ESIMS, FTIR

• -ATR, 1H and 13C NMR spectroscopy and elemental analysis. Keywords: crown ether; dibenzotetraaza[14]annulene; DBTAA; macrocycle; Schiff base; Introduction The design and synthesis of novel polycyclic receptor architecture is of fundamental importance, since model recognition studies contribute to

• showed cation and solvent-induced dimerisation. More recently, Raston et al. reported the synthesis of Goedken’s macrocycle tmtaa nickel(II) complex featuring a single oligo(ethylene glycol) chain strapped across the face of the DBTAA macrocyclic core [28]. However, to the best of our knowledge, there

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

• Marijana Radić Stojković,
• Marko Škugor,
• Łukasz Dudek,
• Jarosław Grolik,
• Julita Eilmes and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

• of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, Poland 10.3762/bjoc.10.225 Abstract An investigation of the interactions of two novel and several known DBTAA–adenine conjugates with double-stranded DNA and RNA has revealed the DNA/RNA groove as the dominant binding site, which is

• in contrast to the majority of previously studied DBTAA analogues (DNA/RNA intercalators). Only DBTAA–propyladenine conjugates revealed the molecular recognition of AT-DNA by an ICD band pattern > 300 nm, whereas significant ICD bands did not appear for other ds-DNA/RNA. A structure–activity relation

• for the studied series of compounds showed that the essential structural features for the ICD recognition are a) the presence of DNA-binding appendages (adenine side chain and positively charged side chain) on both DBTAA side chains, and b) the presence of a short propyl linker, which does not support