Abstract
Two different approaches are offered for the synthesis under mild conditions of disubstituted phenazinium and benzo[a]phenazinium salts. Direct nucleophilic substitutions by primary and secondary amines in quaternary phenazinium salts containing an additional positive charge in the aliphatic part of the molecule were carried out. The substitution proceeds successively in positions 2 and 7, which allows selective introduction of different substituents into the heterocycle. Direct nucleophilic substitution in quaternary 2-N-alkyl-acetamidophenazinium and 5-alkoxy-benzo[a]phenazinium salts with different amines can also serve as a convenient method for the introduction of two different substituents.
Highlights
Phenazine and phenazine-like molecules have a wide spectrum of biological activity [1,2]
Some phenazine derivatives are capable of generating hydroxyl radicals under mild conditions, which enables them to be used as reagents for site-directed DNA scission [6]
The addition of phenazine at 3'- and/or 5'-terminal phosphates of oligonucleotides bearing alkylating groups significantly enhances the stability of oligonucleotide duplexes [7]
Summary
Phenazine and phenazine-like molecules have a wide spectrum of biological activity [1,2]. To estimate the relative reactivity of substituted quaternary phenazinium salts, we calculated the charge distribution for positions 2 and 7 in compounds 1-3,7 and 8 and for positions 5 and 8 in benzo[a]phenazinium derivatives 4-6 (Figure 1). 7-[2-(Methoxycarbonyl)ethyl]amino-9-methyl-2-methylaminophenazinium perchlorate (15) was obtained by reaction of methyl ester of β-alanine with acetamide or of methylamine with acetamide in 51 and 46 % yields, respectively.
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