کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
10587593 | 981431 | 2013 | 7 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Insight into dihalogenation of E-ring of podophyllotoxins, and their acyloxyation derivatives at the C4 position as insecticidal agents
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Unexpected sequential E-ring dihalogenation of podophyllotoxin analogues is reported. It demonstrated that a chlorine/bromine atom was prior introduced at the C2â² position of podophyllotoxin, and the corresponding free rotation of E-ring around the C1-C1â² bond of 2â²-chloro or 2â²-bromopodophyllotoxin was restricted. When 2â²-chloro or 2â²-bromopodophyllotoxin reacted with N-chlorosuccinimide (NCS), the chlorine atom was regioselectively introduced at their C6â² position on the E-ring. Whereas 2â²-chloro or 2â²-bromopodophyllotoxin reacted with NBS, the bromine atom was regioselectively introduced at their C5 position on the B-ring. When 2â²-chloropodophyllotoxin reacted with different carboxylic acids in the presence of BF3·Et2O, the steric effect of its E-ring for stereoselective synthesis of 4β-acyloxy-2â²-chloropodophyllotoxin derivatives was observed. The insecticidal activity of 2â²(2â²,6â²)-(di)halogen-substituted podophyllotoxin derivatives were evaluated with Mythimna separata Walker.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 23, Issue 20, 15 October 2013, Pages 5592-5598
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 23, Issue 20, 15 October 2013, Pages 5592-5598
نویسندگان
Zhiping Che, Xiang Yu, Lingling Fan, Hui Xu,