کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1393981 1501124 2015 12 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of functionalized 3-, 5-, 6- and 8-aminoquinolines via intermediate (3-pyrrolin-1-yl)- and (2-oxopyrrolidin-1-yl)quinolines and evaluation of their antiplasmodial and antifungal activity
ترجمه فارسی عنوان
سنتز 3، 5، 6 و 8-آمینوینولین های فعال شده با استفاده از 3-پریرولین-1-ییل- و (2-اکسپیررولیدین-1-ییل) کینولین ها و ارزیابی فعالیت ضد پلاسمودیومی و ضد قارچی آنها
کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی


• Synthetic exploration of 3-, 5-, 6- and 8-aminoquinolines.
• Novel (3-pyrrolin-1-yl)- and (2-oxopyrrolidin-1-yl)quinoline building blocks.
• Moderate antiplasmodial but significant antifungal activities.

(3-Pyrrolin-1-yl)- and (2-oxopyrrolidin-1-yl)quinolines were prepared via cyclization of diallylaminoquinolines and 4-chloro-N-quinolinylbutanamides, respectively, as novel synthetic intermediates en route to N-functionalized 3-, 5-, 6- and 8-aminoquinolines with potential biological activity. (3-Pyrrolin-1-yl)quinolines were subjected to bromination reactions, and the reactivity of (2-oxopyrrolidin-1-yl)quinolines toward lithium aluminum hydride and methyllithium was assessed, providing an entry into a broad range of novel functionalized (pyrrolidin-1-yl)- and (hydroxyalkylamino)quinolines. Antiplasmodial evaluation of these novel quinolines and their functionalized derivatives revealed moderate micromolar potency against a chloroquine-sensitive strain of the malaria parasite Plasmodium falciparum, and the two most potent compounds also showed micromolar activity against a chloroquine-resistant strain of P. falciparum. Antifungal assessment of (hydroxyalkylamino)quinolines revealed three compounds with promising MIC values against Rhodotorula bogoriensis and one compound with potent activity against Aspergillus flavus.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 92, 6 March 2015, Pages 91–102
نویسندگان
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