کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1394990 1501192 2010 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Identification of benzofuro[2,3-b]quinoline derivatives as a new class of antituberculosis agents
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Identification of benzofuro[2,3-b]quinoline derivatives as a new class of antituberculosis agents
چکیده انگلیسی

A series of 11-alkoxylated and 11-aminated benzofuro[2,3-b]quinoline derivatives were designed, synthesized, and evaluated for their anti-TB and cytotoxic activities. The known 11-chlorobenzofuro[2,3-b]quinoline (3) was synthesized in a single step from anthranilic acid and 2-coumaranone in phosphorus oxychloride in 51% yield for the first time. Treatment of 3 with alcohols and amines gave 11-alkoxylated and 11-aminated benzofuro[2,3-b]quinoline derivatives respectively, which were evaluated for their anti-TB and cytotoxic activities. Our results indicated that 11-arylaminated derivatives were more active than their respective 11-aryloxylated isosteric isomers against Mycobacterium tuberculosis. Among the tested compounds, 11-methoxybenzofuro[2,3-b]quinoline (4), 11-methylamino- benzofuro[2,3-b]quinoline (9), and 11-dimethylaminobenzofuro[2,3-b]quinoline (14) exhibited significant activities against the growth of M. tuberculosis (MIC values of <0.20 μg/mL) and low cytotoxicities against VERO cell with IC50 values of 11.77, 5.55, and >30.00 μg/mL respectively. The selectivity index (SI = IC50/MIC) for 4, 9, and 14 was greater than 58.85, 27.75, and 150 respectively.

Compounds 4, 9, and 14 exhibited significant activities against the growth of M. tuberculosis with a selectivity index (SI) of greater than 58, 27, and 150 respectively.Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 45, Issue 2, February 2010, Pages 602–607
نویسندگان
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