کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1258064 | 971599 | 2009 | 4 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Synthesis and cytotoxicity of 28-carboxymethoxy lupane triterpenoids. Preference of 28-O-acylation over 28-O-alkylation of betulin by ethyl bromoacetate
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی (عمومی)
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
28-Carboxymethoxy lupane tritepenoids 3 and 4 were synthesized by alkylation of betulin with the THP protected 2-hydroxyethyl iodide followed by oxidation and reduction. Direct reaction of betulin (5) or betulone (10) with ethyl bromoacetate led to 28-O-acylation, instead of 28-O-alkylation. The targeted compounds 3 and 4 were not cytotoxic at the highest concentration tested (75 μmol/L), suggesting that elongation of the chain length at the 28-position in both betulinic acid (1) and betulonic acid (2) was detrimental to the cytotoxicity. The acylation products 28-O-bromoacetates (8a, 8b and 11) and 28-O-methoxyacetate 13 exhibited cytotoxicity against several cancer cell lines tested.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Chinese Chemical Letters - Volume 20, Issue 10, October 2009, Pages 1141-1144
Journal: Chinese Chemical Letters - Volume 20, Issue 10, October 2009, Pages 1141-1144
نویسندگان
Aye Aye Mar, Ali Koohang, Nathan D. Majewski, Erika L. Szotek, David A. Eiznhamer, Michael T. Flavin, Ze Qi Xu,