کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
2028504 1542732 2011 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Azido analogs of neuroactive steroids
موضوعات مرتبط
علوم زیستی و بیوفناوری بیوشیمی، ژنتیک و زیست شناسی مولکولی زیست شیمی
پیش نمایش صفحه اول مقاله
Azido analogs of neuroactive steroids
چکیده انگلیسی

Analogs of pregnanolone (3α-hydroxy-5β-pregnan-20-one), modified in position 17 were prepared. Compounds with 20-keto pregnane side chain replaced completely by azide (17α- and 17β-azido-5β-androstan-3α-ol), compounds with its part replaced (20-azido-21-nor-5β-pregnan-3α-ol), and compounds with keto group only replaced ((20R)- and (20S)-20-azido-5β-pregnan-3α-ol) were synthesized using tosylate displacements with sodium azide or Mitsunobu reaction with azoimide. All five azido steroids were converted into corresponding sulfates. Subsequent tests for inhibition of glutamate induced response on NMDA receptors revealed that modification of pregnanolone sulfate side chain with azide did not disturb the activity and some of sulfates tested were more active than parent compound.


► Azides in hindered position 17 of androstane skeleton were synthesized.
► Substitution of tosylate with azide and Mitsunobu reaction were compared.
► Five azido analogs of pregnanolone sulfate altered in 17 side chain were prepared.
► Azido analogs of pregnanolone sulfate inhibited NMDA receptor activity.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Steroids - Volume 76, Issues 10–11, September–October 2011, Pages 1043–1050
نویسندگان
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