Room temperature synthesis and antibacterial activity of new sulfonamides containing n,n-diethyl-substituted amido moieties.

International Journal of Medicinal Chemistry Pub Date : 2012-01-01 Epub Date: 2012-10-17 DOI:10.1155/2012/367815
Olayinka O Ajani, Oluwole B Familoni, Feipeng Wu, Johnbull O Echeme, Zheng Sujiang
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引用次数: 8

Abstract

Sulfonamide drugs which have brought about an antibiotic revolution in medicine are associated with a wide range of biological activities. We have synthesized a series of α-tolylsulfonamide, 1–11 and their substituted N,N-diethyl-2-(phenylmethylsulfonamido) alkanamide derivatives, 12–22 in improved and excellent yields in aqueous medium at room temperature through highly economical synthetic routes. The chemical structures of the synthesized compounds 1–22 were confirmed by analytical and spectral data such as IR, 1H- and 13C-NMR, and mass spectra. The in vitro antibacterial activity of these compounds along with standard clinical reference, streptomycin, was investigated on two key targeted organisms. It was observed that 1-(benzylsulfonyl)pyrrolidine-2-carboxylic acid, 2 emerged as the most active compound against Staphylococcus aureus at MIC value of 1.8 μg/mL while 4-(3-(diethylamino)-3-oxo-2-(phenylmethylsulfonamido) propyl)phenyl phenylmethanesulfonate, 22 was the most active sulfonamide scaffold on Escherichia coli at MIC value of 12.5 μg/mL.

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含n,n-二乙基取代氨基的新型磺胺类化合物的室温合成及其抗菌活性。
磺胺类药物引起了医学上的抗生素革命,它与广泛的生物活性有关。通过经济的合成路线,在室温条件下,以较好的收率合成了一系列α-甲磺酰胺、1-11及其取代的N,N-二乙基-2-(苯基甲基磺酰胺)烷酰胺衍生物、12-22。合成的化合物1-22的化学结构通过IR、(1)H-和(13)C-NMR以及质谱等分析和光谱数据得到了证实。研究了这些化合物与标准临床参考链霉素对两种关键目标生物的体外抗菌活性。结果表明,1-(苄基磺酰基)吡咯烷-2-羧酸,2对金黄色葡萄球菌的抑制活性最高,MIC值为1.8 μg/mL; 4-(3-(二乙胺)-3-氧基-2-(苯基甲基磺酰胺)丙基)苯基苯基甲基甲磺酸,22对大肠杆菌的抑制活性最高,MIC值为12.5 μg/mL。
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期刊介绍: International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis. International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis.
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