2-(N-acyl) and 2-N-acyl-N(6)-substituted analogues of adenosine and
their affinity at the human adenosine receptors
P. Jagtap, Z. Chen, C. Szabo, und K. Klotz. Bioorg Med Chem Lett, 14 (6):
1495-8(März 2004)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..
Zusammenfassung
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.
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.
%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
}