Synthesis and DNA-Binding Properties of 9-Formylacridine and 9-Formylanthracene Aminoacetylhydrazones

Abstract

The dependence of the affinity of compounds to DNA on the structure of their fragments intercalating into the double helix was studied in a series of aminoacetylhydrazones of 9-formylacridine and 9-formylanthracene. The synthesized compounds were characterized by the intercalating properties and the ability to inhibit the polymerase chain reaction (PCR). The affinity to DNA was found to be higher for acridine derivatives (log K a = 7.37 -8.04) than for anthracene derivatives (log K a = 5.37 -6.12). At the same time, both acridines and anthracenes showed insignificant ability to inhibit PCR. Thus, no correlation between the affinity to DNA and the ability to inhibit DNA replication was observed for the compounds studied. 183 0091-150X/05/3904-0183

A Wittig-olefination–Claisen-rearrangement approach to the 3-methylquinoline-4-carbaldehyde synthesis

“…3-Substituted quinoline-4-carbaldehyde derivatives are used in the development of molecular probes for the identification of extra interaction sites in the midgorge and peripheral sites of butyrylcholinesterase (BuChE) [7]. These derivatives are also exploited in the synthesis of DNA binders [8], macrolides [9], antitumor agents [10] and for the treatment of viral and parasitic infections [11]. …”