کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
2027712 1542704 2015 10 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Total synthesis of biologically active 20S-hydroxyvitamin D3
موضوعات مرتبط
علوم زیستی و بیوفناوری بیوشیمی، ژنتیک و زیست شناسی مولکولی زیست شیمی
پیش نمایش صفحه اول مقاله
Total synthesis of biologically active 20S-hydroxyvitamin D3
چکیده انگلیسی


• Key intermediates 7 and 12 were generated in parallel via modified synthetic ways.
• Simultaneous removal of EOM and TBS was completed using camphorsulfonic acid.
• 20S-Hydroxyvitamin D3 was synthesized in 16 steps with an overall yield of 0.4%.
• Synthetic 20S-(OH)D3 activated VDR and initiated expression of downstream genes.
• 20S-(OH)D3 was potent in inhibition of melanoma cells proliferation.

A total synthetic strategy of 20S-hydroxyvitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig–Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated vitamin D receptor (VDR) and initiated the expression of downstream genes. In addition, 20S-(OH)D3 showed similar inhibitory potency as calcitriol [1,25(OH)2D3] on proliferation of melanoma cells.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Steroids - Volume 104, December 2015, Pages 153–162
نویسندگان
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