Ghent University Academic Bibliography

Advanced

N6-Cyclopentyl-3'-substituted-xylofuranosyladenosines: a new class of non-xanthine adenosine A1 receptor antagonists

Serge Van Calenbergh UGent, Jacobien K von Frijtag, Drabbe Künzel, Norbert M Blaton, Oswald M Peeters, Jef Rozenski, Arhtur Van Aerschot, André De Bruyn, Denis De Keukeleire, Adriaan P IJzeman, et al. (1997) JOURNAL OF MEDICINAL CHEMISTRY. 40(23). p.3765-3772
abstract
The present study explores the C-3' site of the 3-deoxy-3-xylofuranosyl ring of nucleoside analogues with an adenine or N-6-cyclopentyladenine (CPA) base moiety and evaluates the effect on adenosine receptor affinity. Two series of sugar-modified adenosines, i.e., 3'-amido-3'-deoxyadenosines and 3'-amidated 3'-deoxyxylofuranosyladenines, were synthesized and tested for their affinity at A(1) and A(2a) receptors in rat brain cortex and rat striatum, respectively. The modest affinity found in the ''xylo series'' prompted us to synthesize the corresponding N-6-cyclopentyl derivatives, which proved to be well accommodated by the A(1) receptors with potencies in the lower nanomolar range. This represents a new perspective in the purinergic field. The absence of a GTP-induced shift, i.e., the ratio between the affinities measured in the presence and absence of 1 mM GTP indicates an antagonistic behavior of this new class of CPA analogues.
Please use this url to cite or link to this publication:
author
organization
alternative title
N-6-Cyclopentyl-3'-substituted-xylofuranosyladenosines : a new class of non-xanthine adenosine A(1) receptor antagonists
year
type
journalArticle (original)
publication status
published
subject
keyword
DEHYDROGENASE, 2'-DEOXY-2'-(3-METHOXYBENZAMIDO)ADENOSINE, NUCLEOSIDES, INHIBITOR, POTENTIAL PARTIAL AGONISTS, ACID RELATED-COMPOUNDS, RAT-BRAIN, ANALOGS
journal title
JOURNAL OF MEDICINAL CHEMISTRY
J. Med. Chem.
volume
40
issue
23
pages
3765 - 3772
Web of Science type
Article
ISSN
0022-2623
DOI
10.1021/jm970176k
language
English
UGent publication?
yes
classification
A1
id
185749
handle
http://hdl.handle.net/1854/LU-185749
date created
2004-01-14 13:41:00
date last changed
2017-03-09 15:42:02
@article{185749,
  abstract     = {The present study explores the C-3' site of the 3-deoxy-3-xylofuranosyl ring of nucleoside analogues with an adenine or N-6-cyclopentyladenine (CPA) base moiety and evaluates the effect on adenosine receptor affinity. Two series of sugar-modified adenosines, i.e., 3'-amido-3'-deoxyadenosines and 3'-amidated 3'-deoxyxylofuranosyladenines, were synthesized and tested for their affinity at A(1) and A(2a) receptors in rat brain cortex and rat striatum, respectively. The modest affinity found in the ''xylo series'' prompted us to synthesize the corresponding N-6-cyclopentyl derivatives, which proved to be well accommodated by the A(1) receptors with potencies in the lower nanomolar range. This represents a new perspective in the purinergic field. The absence of a GTP-induced shift, i.e., the ratio between the affinities measured in the presence and absence of 1 mM GTP indicates an antagonistic behavior of this new class of CPA analogues.},
  author       = {Van Calenbergh, Serge and von Frijtag, Jacobien K and K{\"u}nzel, Drabbe  and Blaton, Norbert M and Peeters, Oswald M and Rozenski, Jef and Van Aerschot, Arhtur and De Bruyn, Andr{\'e} and De Keukeleire, Denis and IJzeman, Adriaan P and Herdewijn, Piet},
  issn         = {0022-2623},
  journal      = {JOURNAL OF MEDICINAL CHEMISTRY},
  keyword      = {DEHYDROGENASE,2'-DEOXY-2'-(3-METHOXYBENZAMIDO)ADENOSINE,NUCLEOSIDES,INHIBITOR,POTENTIAL PARTIAL AGONISTS,ACID RELATED-COMPOUNDS,RAT-BRAIN,ANALOGS},
  language     = {eng},
  number       = {23},
  pages        = {3765--3772},
  title        = {N6-Cyclopentyl-3'-substituted-xylofuranosyladenosines: a new class of non-xanthine adenosine A1 receptor antagonists},
  url          = {http://dx.doi.org/10.1021/jm970176k},
  volume       = {40},
  year         = {1997},
}

Chicago
Van Calenbergh, Serge, Jacobien K von Frijtag, Drabbe Künzel, Norbert M Blaton, Oswald M Peeters, Jef Rozenski, Arhtur Van Aerschot, et al. 1997. “N6-Cyclopentyl-3’-substituted-xylofuranosyladenosines: a New Class of Non-xanthine Adenosine A1 Receptor Antagonists.” Journal of Medicinal Chemistry 40 (23): 3765–3772.
APA
Van Calenbergh, S., von Frijtag, J. K., Künzel, D., Blaton, N. M., Peeters, O. M., Rozenski, J., Van Aerschot, A., et al. (1997). N6-Cyclopentyl-3’-substituted-xylofuranosyladenosines: a new class of non-xanthine adenosine A1 receptor antagonists. JOURNAL OF MEDICINAL CHEMISTRY, 40(23), 3765–3772.
Vancouver
1.
Van Calenbergh S, von Frijtag JK, Künzel D, Blaton NM, Peeters OM, Rozenski J, et al. N6-Cyclopentyl-3’-substituted-xylofuranosyladenosines: a new class of non-xanthine adenosine A1 receptor antagonists. JOURNAL OF MEDICINAL CHEMISTRY. 1997;40(23):3765–72.
MLA
Van Calenbergh, Serge, Jacobien K von Frijtag, Drabbe Künzel, et al. “N6-Cyclopentyl-3’-substituted-xylofuranosyladenosines: a New Class of Non-xanthine Adenosine A1 Receptor Antagonists.” JOURNAL OF MEDICINAL CHEMISTRY 40.23 (1997): 3765–3772. Print.