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

IF 0.9 Q4 CHEMISTRY, MULTIDISCIPLINARY
V. Milata, Maroš Bella, Robert Kurinec
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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.
具有良好生物和络合活性的3-羟甲基-1,4-二氢-4-氧喹啉类化合物
羟甲基存在于许多有用的和具有生物效力的物质中,如糖、曲酸(Bajpai, 1982)、硝基醇(3-羟甲基吡啶)(Moncol, 2006;Broghammer, 1967)或羟基甲基苯酚-酚醛中间体(Baekeland, 1909)。另一方面,4-喹诺酮类药物如果取代第3位,则是一组具有各种生物活性的抗菌药物,如果取代第2位,则是抗中枢神经系统和类似疾病的药物(犬尿酸衍生物)(Turski, 2013;Szalardy, 2012;费洛浦用,2009)。考虑到这一点,我们对合成3-羟基甲基-1,4二氢-4-氧喹啉很感兴趣。4-喹诺酮类药物是一种众所周知的具有广谱活性的化疗药物(Andriole, 2000;Milata, 2000)基于抑制细菌拓扑异构酶II (DNA旋转酶)和拓扑异构酶IV在革兰氏阳性物种的酶,从而抑制细菌DNA的第三负超卷曲(Gellert, 1976;王,1985;Gootz, 1996),主要与融合吡啶-4- 1 -3-羧酸部分的第3位和第4位氧原子结合(Andriole, 2000)。因此,制备和评价相应的结构基序,即3-羟甲基喹啉- 1是一个值得关注的问题。数据库SciFinder中的亚结构搜索只提供了甲醛与4-喹诺酮类或其前体的各种应用(Goldsworthy, 1982),但没有真正的合成报道。因此,制备了这种具有良好结合和络合活性的化合物。
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来源期刊
Acta Chimica Slovaca
Acta Chimica Slovaca CHEMISTRY, MULTIDISCIPLINARY-
自引率
12.50%
发文量
11
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