Synthesis of somenew hybride molecules containing several azole moieties and investigation of their biological activities.

Bioorganicheskaia khimiia Pub Date : 2014-05-01
Sule Ceylan, Hacer Bayrak, Ahmet Demirbas, Serdar Ulker, Sengul Alpay-Karaoglu, Neslihan Demirbas
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Abstract

1,2,4-Triazole-3-one prepared from tryptamine was converted to the corresponding carbotioamides by several steps. Their treatment with ethyl bromoacetate or 4-chlorophenacyl bromide produced the corresponding 5-oxo-1,3-thiazolidine or 3-(4-chlorophenyl)-1,3-thiazole derivatives. Acetohydrazide derivative that was obtained starting from tryptamine, was converted to the corresponding Schiff basis and sulfonamide by the treatment with suitable aldehydes and benzensulphonyl chloride, respectively. 2-[(4-Amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-3-yl)methyl]-4-[2-(1H-indole-3-yl)ethyl]-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one was synthesized starting from hydrazide via the formation of the corresponding 1,3,4-oxadiazole compound, while the other bitriazole compounds were obtained by intramolecular cyclisation of carbothioamides in basic media. The treatment of 1,2,4-triazole or 1,3,4-oxadiazole compound with several amines generated the corresponding Mannich bases. Ethyl (2-amino-1,3-thiazole-4-yl)acetate was converted to the corresponding 1,3,4-oxadiazole derivative, arylidenehydrazides, 1,2,4-triazole-3-one and 5-oxo-1,3-oxazolidine derivatives by several steps. The structural assignments of new compounds were based on their elemental analysis and spectral (FT IR, 1H NMR, 13C NMR and LC-MS) data. The antimicrobial, antilipase and antiurease activity studies revealed that some of the synthesized compounds showed antimicrobial, antilipase and/or antiurease activity.

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几种含氮杂合分子的合成及其生物活性研究。
由色胺制备的1,2,4-三唑-3-酮经过几个步骤转化为相应的碳酰胺。用溴乙酸乙酯或4-氯苯酰溴处理后,可制得相应的5-氧-1,3-噻唑烷或3-(4-氯苯基)-1,3-噻唑衍生物。以色胺为原料得到的乙酰肼衍生物,经适当的醛和苯磺酰氯处理,分别转化为相应的希夫碱和磺胺。2-[(4-氨基-5-硫氧基-4,5-二氢- 1h -1,2,4-三唑-3-基)甲基]-4-[2-(1h -吲哚-3-基)乙基]-5-甲基-2,4-二氢- 3h -1,2,4-三唑-3-酮],其他双三唑化合物则是在碱性介质中通过碳硫酰胺分子内环化得到的。1,2,4-三唑或1,3,4-恶二唑化合物与几种胺处理后生成相应的Mannich碱。乙酸乙酯(2-氨基-1,3-噻唑-4-基)经几个步骤转化为相应的1,3,4-恶二唑衍生物、芳基肼、1,2,4-三唑-3- 1和5-氧-1,3-恶唑烷衍生物。根据元素分析和光谱(FT IR, 1H NMR, 13C NMR和LC-MS)数据确定了新化合物的结构。抗菌、抗脂肪酶和抗脲酶活性研究表明,部分合成的化合物具有抗菌、抗脂肪酶和/或抗脲酶活性。
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