3-Hydroxymethyl-1,4-dihydro-4-oxoquinoline like compound with promising biological and complexing activity

Abstract

Hydroxymethyl group is present in many useful and biologically potent substances like sugars, kojic acid (Bajpai, 1982), ronicol (3-hydroxymethylpyridine) (Moncol, 2006; Broghammer, 1967) or hydroxymethylphenol — intermediate for bakelite (Baekeland, 1909). On the other hand, 4-quinolones are a group of antibacterials with various biological activities if substituted in position 3and they are anti-CNS and similar diseases agents if substituted in position 2(kynurenic acid derivatives) (Turski, 2013; Szalardy, 2012; Fulop, 2009). Considering this, we were interested in the synthesis of 3-hydroxymethyl-1,4dihydro-4-oxoquinoline. 4-Quinolones are a well-known group of chemotherapeutics with a broad spectrum of activities (Andriole, 2000; Milata, 2000) based on inhibition of the enzyme of bacterial topoisomerase II (DNA gyrase) and topoisomerase IV in Gram-positive species, thus inhibiting tertiary negative supercoiling of bacterial DNA (Gellert, 1976; Wang, 1985; Gootz, 1996) mostly bound to oxygen atoms in positions 3and 4of the fused pyrid-4-one-3-carboxylic acid moiety (Andriole, 2000). Therefore, it should be interesting to prepare and evaluate the corresponding structural motif, namely 3-hydroxymethylquinol4-one. Substructural search in database SciFinder provided only various applications of formaldehyde with 4-quinolones or their precursors (Goldsworthy, 1982) but no true synthesis has been reported. Therefore, this compound with promising binding and complexing activity has been prepared.