Synthesis of 1,5-Anhydro-2-(N⁶-Cyclopentyladenin-9-Yl)-2-Deoxy-D-Altrohexitol

I. Verheggen Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000, Leuven, (Belgium)

A. Van Aerschot Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000, Leuven, (Belgium)

N. Pillet Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000, Leuven, (Belgium)

E. M. van der Wenden Center for Bio-pharmaceutical Sciences, Division of Medicinal Chemistry, Leiden University, 2300, RA, Leiden, (The Netherlands)

A. Ijzerman Center for Bio-pharmaceutical Sciences, Division of Medicinal Chemistry, Leiden University, 2300, RA, Leiden, (The Netherlands)

P. Herdewijn Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000, Leuven, (Belgium)

Abstract

The N ⁶-cyclopentyladenosine (CPA) analogue (4) was synthesized in 10 steps starting from glucose. The results of the radioligand binding assays are consistent with the thus far published findings that compounds containing a six-membered moiety at N ⁹ exhibit extremely weak affinity for adenosine receptors. Replacement of the ribofuranosyl moiety of CPA (2) by a 2-deoxy-D-altrohexitol moiety is sufficient to completely abolish its agonist activity.

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Synthesis of 1,5-Anhydro-2-(N⁶-Cyclopentyladenin-9-Yl)-2-Deoxy-D-Altrohexitol

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Synthesis of 1,5-Anhydro-2-(N6-Cyclopentyladenin-9-Yl)-2-Deoxy-D-Altrohexitol

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Synthesis of 1,5-Anhydro-2-(N⁶-Cyclopentyladenin-9-Yl)-2-Deoxy-D-Altrohexitol