کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
10588533 | 981474 | 2010 | 7 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Design and synthesis of biphenyl derivatives as mushroom tyrosinase inhibitors
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Two new series of biphenyls, analogs of aglycone of natural product fortuneanoside E, were prepared using Suzuki-Miyaura cross-coupling and selective magnesium iodide demethylation/debenzylation, and their mushroom tyrosinase inhibitory activity was evaluated. Most of the 4-hydroxy-3,5-dimethoxyphenyl biphenyl compounds (series II, 20-36) were in general more active than 3,4,5-trimethoxyphenyl biphenyl compounds (series I, 1-19). Structure-activity relationships study showed that monosaccharide substituents, such as glucose, were not necessary and the presence of 4-hydroxy-3,5-dimethoxyphenyl moiety was crucial for inhibitory activity. Among the compounds synthesised, compound 21 (IC50 = 0.02 mM) was found to be the most active one, which exhibited an activity that was 7 times higher than that of fortuneanoside E (IC50 = 0.14 mM) and 10 times higher than that of arbutin (IC50 = 0.21 mM), known as potent tyrosinase inhibitors. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 21 was a competitive inhibitor (Ki = 0.015 mM).
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry - Volume 18, Issue 18, 15 September 2010, Pages 6708-6714
Journal: Bioorganic & Medicinal Chemistry - Volume 18, Issue 18, 15 September 2010, Pages 6708-6714
نویسندگان
Kai Bao, Yi Dai, Zhi-Bin Zhu, Feng-Juan Tu, Wei-Ge Zhang, Xin-Sheng Yao,