کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1370012 981802 2016 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of tetracyclic iminosugars fused benzo[e][1,3]thiazin-4-one and their HIV-RT inhibitory activity
ترجمه فارسی عنوان
سنتز آنزیم های گوگردی tetracyclic با ترکیب بنزو [e] [1،3] تیازین-4-one و فعالیت مهار کننده HIV-RT
کلمات کلیدی
آنزیم گوگرد tetracyclic؛ بنزو [e] [1،3] تیازین-4-one؛ آساز C-pseudonucleoside؛ یک واکنش سه جزء؛ فعالیت ضد HIV HIV RT
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی

Several aza-C-pseudonucleosides bearing 1,3-benzothiazin-4-one (6 and 7) were prepared by the one-pot three-component condensation from the iminosugar aldehyde 3, amino acid ethyl/methyl ester hydrochlorides 4(a–c), and 2-mercaptobenzoic acid 5. After removal of Boc and the isopropylidene groups, the target novel tetracyclic iminosugars fused benzo[e][1,3]thiazin-4-one 1(a–c) and 2(a–b) were first afforded by the intramolecular cyclo-amidation reaction. Their structures were determined by their 1H, 13C NMR, and HRMS (ESI) spectra and X-ray. The tetracyclic iminosugars 1(a–c) and 2(a–b) were examined for their HIV reverse transcriptase (RT) inhibitory activities. The result showed that all compounds could effectively inhibit RT activity. Among them, compound 2a was the best one with the IC50 value of RT inhibitory activity of 0.82 μM. Structure–activity relationship analysis suggested that 1′R configuration in the tetracyclic azasugars was of benefit to their anti-HIV RT activity.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 26, Issue 7, 1 April 2016, Pages 1738–1741
نویسندگان
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