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

(1997) JOURNAL OF MEDICINAL CHEMISTRY. 40(23). p.3765-3772
Author
Organization
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.
Keywords
DEHYDROGENASE, 2'-DEOXY-2'-(3-METHOXYBENZAMIDO)ADENOSINE, NUCLEOSIDES, INHIBITOR, POTENTIAL PARTIAL AGONISTS, ACID RELATED-COMPOUNDS, RAT-BRAIN, ANALOGS

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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.
@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},
}

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