GP3269

GP3269
Identifiers
	IUPAC name (2R,3R,4S,5R)-2-[4-(4-fluoroanilino)-5-phenylpyrrolo[2,3-d]pyrimidin-7-yl]-5-methyloxolane-3,4-diol;
CAS Number	186393-42-0;
PubChem CID	9802216;
ChemSpider	7977978;
ChEMBL	ChEMBL66277;
Chemical and physical data
Formula	C23H21FN4O3
Molar mass	420.444 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C3=C(N=CN=C32)NC4=CC=C(C=C4)F)C5=CC=CC=C5)O)O;
	InChI InChI=1S/C23H21FN4O3/c1-13-19(29)20(30)23(31-13)28-11-17(14-5-3-2-4-6-14)18-21(25-12-26-22(18)28)27-16-9-7-15(24)8-10-16/h2-13,19-20,23,29-30H,1H3,(H,25,26,27)/t13-,19-,20-,23-/m1/s1; Key:MULTXXBUCOCYME-HYYMDVBZSA-N;

GP3269 is an experimental drug that acts as a selective inhibitor of the enzyme adenosine kinase. In animal studies it has analgesic and anticonvulsant effects.^[1]^[2]^[3]

References

^ Erion MD, Ugarkar BG, DaRe J, Castellino AJ, Fujitaki JM, Dixon R, et al. (1997). "Design, Synthesis and Anticonvulsant Activity of the Potent Adenosine Kinase Inhibitor GP3269". Nucleosides and Nucleotides. 16 (7–9): 1013–1021. doi:10.1080/07328319708006124.
^ Bookser BC, Ugarkar BG, Matelich MC, Lemus RH, Allan M, Tsuchiya M, et al. (December 2005). "Adenosine kinase inhibitors. 6. Synthesis, water solubility, and antinociceptive activity of 5-phenyl-7-(5-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidines substituted at C4 with glycinamides and related compounds". Journal of Medicinal Chemistry. 48 (24): 7808–7820. doi:10.1021/jm050394a. PMID 16302820.
^ Szentmiklósi AJ, Cseppento A, Harmati G, Nánási PP (2011). "Novel trends in the treatment of cardiovascular disorders: site- and event- selective adenosinergic drugs". Current Medicinal Chemistry. 18 (8): 1164–1187. doi:10.2174/092986711795029753. PMID 21291368.

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