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首页> 外文期刊>The Internet Journal of Pharmacology >Synthesis And Anti Microbial Studies Of Certain Schiff Bases Containing 1,8-Naphthyridine Moiety
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Synthesis And Anti Microbial Studies Of Certain Schiff Bases Containing 1,8-Naphthyridine Moiety

机译：某些含1,8-萘啶部分的席夫碱的合成及抗菌研究

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Keeping in view of the biological potential of Schiff bases attached to heterocyclic ring system the synthesis of certain Schiff bases containing 1,8-naphthyridines were undertaken.2-amino nicotinaldehyde on condensation with ethyl cyano acetate yielded 2-hydroxy-3-cyano-1,8-naphthyridine.(I) This upon treatment with 10% NaoH solution gave 2-hydroxy-1,8-naphthyridine-3-carboxylic acid. (II). Compound II on treatment with phosphorus oxy chloride gave 2-chloro-1,8-naphthyridine-3-carboxylic acid.(III). The compound (III) upon treatment with hydrazine hydrate in ethanol gave 2-hydrazido-1,8-naphthyridine-3-carboxylic acid. (Va-d) which are schiff’s bases. The schiff’s bases on treatment with trietyhl amine in dry 1,4-dioxan and mono chloro acetyl chloride yielded 3-chloro-4-(substituted phenyl)-1-(3-carboxy-1,8-naphthyridin-2-yl amino)-azetidin-2-one.(Via-d). The constitution of all compounds synthesized was established by elemental analysis and spectral studies. Allcompounds were evaluated for antibacterial and antifungal activites against different strains of bacterial and fungal organisms. Some of the compounds exhibited significant anti bacterial activity. Introduction Sciff bases are condensation products of primary amines and aromatic aldehydes. They are known to exhibit potent antibacterial , anticonvulsant, anti inflammatory activities1. In addition some Schiff bases show pharmacologically useful activities like anticancer2, anti hypertensive and hypnotic3 activities. Heterocyclic compounds like 1,8-naphthyridines arouse great interest due to diverse type of biological activity associated with it, viz. antimalarial, anticancer, anticonvulsant,4 antibacterial and diuretic. Combination of two or more moieties into one is a common procedure for manipulation in medicinal chemistry and this can possibly result in augmenting the activity, removal of untoward side effects and particularly prevent the development of resistance by infectious micro organisms. In view of these facts, synthesis of certain Schiff bases containing 1,8-naphthyridine moiety has been under taken in the hope of getting better bioactive agents. For the synthesis of such compounds, 2-amino nicotinaldehyde was treated with ethyl cyano acetate to get 2-hydroxy -3-cyano-1,8-naphtyridine. (I). This upon treatment with 10% NaoH solution gave 2-hydroxy-1,8-naphthyridine-3-carboxylic acid. (II). Compound II on treatment with phosphorus oxy chloride gave 2-chloro-1,8-naphthyridine-3-carboxylic acid.(III). The intermediate (III) upon treatment with hydrazine hydrate in ethanol gave 2-hydrzido-1,8-naphthyridine-3-carboxylic acid. (V). The constitution of all compounds synthesized was established by elemental analysis, UV, IR and NMR and mass spectral study. Selected compounds were evaluated for antibacterial and antifungal activites. Experimental Melting points were determined by open capillary tube method and are uncorrected. TLC was run on Silica gel G-plates using Benzene-Methanol as developing solvent. FTIR (cm1 and PMR spectra chemical shift in delta ppm downfield from TMS) were recorded on Jasco FTIR 410 spectrophotometer and AMX-400 MHz spectrophotometers respectively. Synthesis Of 3-Cyano-2-Hydroxy-1,8-Naphthyridine- (I) A mixture of 2-amino nicotinaldehyde7 (0.01mole ) and ethyl cyano acetate (0.01)was refluxed in ethanol containing a few drops piperidine for a period of six hours,cooled, the solid separated was separated was filtered and recrystallised from ethyl acetate-acetone solvent pair. Synthesis Of 2-Hydroxy-1,8-Naphthyridin-3-Carboxylic Acid-(Ii) A mixture of 2-hydroxy-3-cyano-1,8-naphthyridin (0.01mole),50 ml of 10% sodium hydroxide solution and 10 ml of alcohol was refluxed for one and a half hours. The solution was boiled in the open flask for a few minutes. The solution was cooled and conc. hydrochloric acid was added, till the precipitation was complete. The product was filtered and washed with water and recrystallised from methanol.Synthesis Of
机译：考虑到席夫碱与杂环系统连接的生物学潜力，进行了某些含有1,8-萘啶的席夫碱的合成。2-氨基烟醛与氰基乙酸乙酯缩合生成2-羟基-3-氰基-1 ，8-萘啶。（I）用10％NaoH溶液处理后得到2-羟基-1，8-萘啶-3-羧酸。 （II）。用氯氧化磷处理的化合物Ⅱ得到2-氯-1，8-萘啶-3-羧酸（Ⅲ）。用乙醇中的水合肼处理化合物（Ⅲ）后得到2-肼基-1，8-萘啶-3-羧酸。 （Va-d）是席夫的基地。席夫氏碱基于在干燥的1,4-二恶烷中用三苯乙胺处理和单氯乙酰氯得到3-氯-4-（取代的苯基）-1-（3-羧基-1,8-萘啶-2-基氨基） -氮杂环丁烷-2-酮（通过-d）。通过元素分析和光谱研究确定了所有合成化合物的组成。评价了所有化合物对不同菌株的细菌和真菌生物的抗菌和抗真菌活性。一些化合物表现出显着的抗细菌活性。简介Sciff碱是伯胺和芳香醛的缩合产物。已知它们具有有效的抗菌，抗惊厥，抗炎活性1。此外，一些席夫碱还显示出药理上有用的活性，例如抗癌，抗高血压和催眠活性。杂环化合物（例如1,8-萘啶）引起了极大的兴趣，因为与之相关的多种生物活性。抗疟疾，抗癌，抗惊厥，4抗菌和利尿剂。将两个或多个部分组合成一个是药物化学中常用的操作步骤，这可能导致活性增加，不良副作用消除，特别是防止传染性微生物产生耐药性。鉴于这些事实，已经进行了某些含有1，8-萘啶部分的席夫碱的合成，以期获得更好的生物活性剂。为了合成这种化合物，将2-氨基烟醛用氰基乙酸乙酯处理，得到2-羟基-3-氰基-1，8-萘啶。 （一世）。用10％NaoH溶液处理后得到2-羟基-1,8-萘啶-3-羧酸。 （II）。用氯氧化磷处理的化合物Ⅱ得到2-氯-1，8-萘啶-3-羧酸（Ⅲ）。在乙醇中用水合肼处理中间体（III）后得到2-肼基-1,8-萘啶-3-羧酸。 （V）。通过元素分析，UV，IR和NMR以及质谱研究确定了所有合成化合物的组成。评价所选化合物的抗菌和抗真菌活性。实验熔点是通过开放毛细管法测定的，未经校正。 TLC在硅胶G板上运行，使用苯甲醇作为展开剂。 FTIR（cm1和PMR光谱从TMS到低磁场的百万分率下场的化学位移）分别在Jasco FTIR 410分光光度计和AMX-400 MHz分光光度计上记录。 3-Cyano-2-Hydroxy-1,8-Naphthyridine-的合成（I）将2-氨基烟醛7（0.01mole）和氰基乙酸乙酯（0.01）的混合物在含有几滴哌啶的乙醇中回流一段时间。冷却六小时，分离出的固体经过滤并从乙酸乙酯-丙酮溶剂对中重结晶。 2-羟基-1,8-萘啶-3-羧酸的合成-（Ii）2-羟基-3-氰基-1,8-萘啶（0.01mole），50 ml 10％氢氧化钠溶液和将10ml的酒精回流一个半小时。将溶液在敞口烧瓶中煮沸几分钟。将溶液冷却并浓缩。加入盐酸，直到沉淀完全。过滤产物，用水洗涤，并从甲醇中重结晶。

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