کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1392754 1501150 2013 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Design and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A
کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Design and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A
چکیده انگلیسی


• Starting from spiromamakone, a more synthetically accessible template was designed.
• A total of 50 compounds were rapidly constructed and their cytotoxicity was evaluated.
• (±)-7d-II was discovered to be a 15-fold more cytotoxic agent than spiromamakone.
• (±)-7d-II appeared to act in a manner similar to spiromamakone.

The spirocycle is a key structure found in many bioactive compounds. From the cytotoxic and spirocyclic natural product, spiromamakone A (1) and its analogues, a more synthetically accessible spiroacetal template 4 was designed based on structural similarity analysis. A total of 50 compounds were rapidly synthesized in only one or two synthetic steps from the starting compound, and their cytotoxicity was evaluated. As a result, (±)-(2R*,5R*)-2-(4-iodophenyl)-7-chloro-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-one (7d-II) was discovered and found to be fifteen-fold more cytotoxic than 1. The easily accessible spiroacetal 7d-II appeared to act in a manner similar to the highly oxidized natural product, spiromamakone A (1).

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 66, August 2013, Pages 180–184
نویسندگان
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