Shridhar D R, Sastry C V, Moorty S R, Vaidya N K, Reddy P G, Reddi G S, Thapar G S
J Med Chem. 1977 Jan;20(1):149-54. doi: 10.1021/jm00211a032.
A series of new N-(5-substituted 2-furfuryl)-N,N-dimethyl-N-aryloxyalkyl quaternary ammonium salts relating to general structure IV has been synthesized by reacting 5-substituted 2-(N,N-dimethylaminomethyl)furans IIa-d with appropriate aryloxyalkyl bromides III. The resulting compounds are tested for in vitro antimicrobial activity. A simpler synthesis of 5-nitro-2-(N,N-dimethylaminomethyl)furan (IId) involving the reduction of N,N-dimethyl-5-nitro-2-furamide (Ib) with diborane is described. A new compound, 5-bromo-2-(N,N-dimethylaminomethyl)furnan (IIc), is prepared in a similar way. Many of these compounds (22, 28, 34, 37-42, 44, and 45) indicate high activity against Staphylococcus aureus, Streptococcus faecalis, Klebsiella pneumoniae, and Pseudomonas aeruginosa and are more active than nitrofurantoin, Compounds 22, 34 and 41 exhibit the highest in vitro antibacterial activity in the series. Some of these quaternary salts (22, 25, 37, 37-41, and 60) possess appreciable activity against Mycobacterium tuberculosis H37Rv. None of these compounds show significant antifungal activity. Eight compounds (18, 21, 22, 26-28, 32, and 34) have high in vitro antibacterial activity were inactive when tested for anthelmintic activity in rats against Nippostrongylus brasiliensis and Hymenolepis nana.
通过使5-取代的2-(N,N-二甲基氨基甲基)呋喃IIa-d与适当的芳氧基烷基溴化物III反应，合成了一系列与通式IV相关的新型N-(5-取代的2-糠基)-N,N-二甲基-N-芳氧基烷基季铵盐。对所得化合物进行了体外抗菌活性测试。描述了一种更简单的合成5-硝基-2-(N,N-二甲基氨基甲基)呋喃(IId)的方法，该方法涉及用乙硼烷还原N,N-二甲基-5-硝基-2-呋喃甲酰胺(Ib)。以类似方式制备了一种新化合物5-溴-2-(N,N-二甲基氨基甲基)呋喃(IIc)。这些化合物中的许多(22、28、34、37 - 42、44和45)对金黄色葡萄球菌、粪肠球菌、肺炎克雷伯菌和铜绿假单胞菌显示出高活性，并且比呋喃妥因更具活性。化合物22、34和41在该系列中表现出最高的体外抗菌活性。这些季铵盐中的一些(22、25、37、37 - 41和60)对结核分枝杆菌H37Rv具有明显活性。这些化合物均未显示出显著的抗真菌活性。八种具有高体外抗菌活性的化合物(18、21、22、26 - 28、32和34)在大鼠体内针对巴西日圆线虫和微小膜壳绦虫进行驱虫活性测试时无活性。
