{"title":"3-Hydroxymethyl-1,4-dihydro-4-oxoquinoline like compound with promising biological and complexing activity","authors":"V. Milata, Maroš Bella, Robert Kurinec","doi":"10.2478/acs-2019-0025","DOIUrl":null,"url":null,"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.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":"12 1","pages":"182 - 184"},"PeriodicalIF":0.9000,"publicationDate":"2019-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Chimica Slovaca","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2478/acs-2019-0025","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
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.