%0 Journal Article %1 Jagtap2004 %A Jagtap, P. G. %A Chen, Z. %A Szabo, C. %A Klotz, K. N. %D 2004 %J Bioorg Med Chem Lett %K & Adenosine/*analogs Binding/physiology Humans P1/*metabolism Protein Purinergic derivatives/*metabolism Receptor %N 6 %P 1495-8 %T 2-(N-acyl) and 2-N-acyl-N(6)-substituted analogues of adenosine and their affinity at the human adenosine receptors %U http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=15006389 %V 14 %X A series of 2-(N-acyl) and 2-(N-acyl)-N(6)-alkyladenosine analogues have been synthesized from the intermediate 2-amino-6-chloroadenosine derivatives (2b and 7) and evaluated for their affinity at the human A(1), A(2A), and A(3) receptors. We found that 2-(N-acyl) derivatives of adenosine showed relatively low affinity at A(2A) and A(3) receptors, while the N(6)-cyclopentyl substituent in 4h and 4i induced high potency A(1) (K(i))=20.7 and 31.8 nM respectively at the A(1) receptor and resulted therefore in increased selectivity for this subtype. The general synthetic methods and their binding studies are presented herein.

@article{Jagtap2004, abstract = {A series of 2-(N-acyl) and 2-(N-acyl)-N(6)-alkyladenosine analogues have been synthesized from the intermediate 2-amino-6-chloroadenosine derivatives (2b and 7) and evaluated for their affinity at the human A(1), A(2A), and A(3) receptors. We found that 2-(N-acyl) derivatives of adenosine showed relatively low affinity at A(2A) and A(3) receptors, while the N(6)-cyclopentyl substituent in 4h and 4i induced high potency [A(1) (K(i))=20.7 and 31.8 nM respectively] at the A(1) receptor and resulted therefore in increased selectivity for this subtype. The general synthetic methods and their binding studies are presented herein.}, added-at = {2010-12-14T18:12:02.000+0100}, author = {Jagtap, P. G. and Chen, Z. and Szabo, C. and Klotz, K. N.}, biburl = {https://www.bibsonomy.org/bibtex/2e5e896169177b545d350e7f011b4b7d0/pharmawuerz}, endnotereftype = {Journal Article}, interhash = {b3b7cc17b92037c54a88efd0d7ed1df0}, intrahash = {e5e896169177b545d350e7f011b4b7d0}, issn = {0960-894X (Print) 0960-894X (Linking)}, journal = {Bioorg Med Chem Lett}, keywords = {& Adenosine/*analogs Binding/physiology Humans P1/*metabolism Protein Purinergic derivatives/*metabolism Receptor}, month = {Mar 22}, note = {Jagtap, Prakash G Chen, Zhiyu Szabo, Csaba Klotz, Karl-Norbert R44AI46167/AI/NIAID NIH HHS/United States Research Support, U.S. Gov't, P.H.S. England Bioorganic \& medicinal chemistry letters Bioorg Med Chem Lett. 2004 Mar 22;14(6):1495-8.}, number = 6, pages = {1495-8}, shorttitle = {2-(N-acyl) and 2-N-acyl-N(6)-substituted analogues of adenosine and their affinity at the human adenosine receptors}, timestamp = {2010-12-14T18:20:04.000+0100}, title = {2-(N-acyl) and 2-N-acyl-N(6)-substituted analogues of adenosine and their affinity at the human adenosine receptors}, url = {http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=15006389}, volume = 14, year = 2004 }