کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
10591342 | 981749 | 2013 | 5 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Design, synthesis and binding affinity of acetylcholine carbamoyl analogues
ترجمه فارسی عنوان
طراحی، ترکیب و وابستگی آنالوگهای استروئیدی کرباموییل استیل کولین
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
چکیده انگلیسی
A series of acetylcholine carbamoyl analogues, cyclised at the carbamate moiety or at the cationic head or at both, were tested for binding affinity at muscarinic and neuronal nicotinic receptors (nAChRs). While no muscarinic affinity was found, submicromolar Ki values, similar to that of carbachol, were measured at α4β2 nAChRs for the enantiomers of 5-dimethylaminomethyl- and 5-trimethylammoniomethyl-2-oxazolidinone, 2 and 2a, and for (S)-N-methylprolinol carbamate (S)-3. Methylation of oxazolidinone nitrogen of 2 and 2a and of N-methylprolinol nitrogen of (S)-3 and, even more, hybridization of cyclic carbamate substructure (oxazolidinone) with cyclic cationic head (N-methylpyrrolidine) markedly lower the nicotinic affinity. Docking results were consistent with SAR analysis highlighting the interaction capabilities of (R)-2a and (S)-3 and the negative effect of intracyclic nitrogen methylation and of double cyclisation.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 23, Issue 23, 1 December 2013, Pages 6481-6485
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 23, Issue 23, 1 December 2013, Pages 6481-6485
نویسندگان
Cristiano Bolchi, Ermanno Valoti, Matteo Binda, Francesca Fasoli, Rossana Ferrara, Laura Fumagalli, Cecilia Gotti, Rosanna Matucci, Giulio Vistoli, Marco Pallavicini,