N6-Cyclopentyladenosine

N⁶-Cyclopentyladenosine (CPA) is a drug which acts as a selective adenosine A₁ receptor agonist.^[1] It has mainly cardiovascular effects with only subtle alterations of behavior.^[2] CPA is widely used in scientific research into the adenosine receptors and has been used to derive a large family of derivatives.^[3]^[4]^[5]^[6]^[7]

Quick facts Names, Identifiers ...

N⁶-Cyclopentyladenosine
Names

IUPAC name N⁶-Cyclopentyladenosine
Systematic IUPAC name (2R,3R,4S,5R)-2-[6-(Cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Identifiers
CAS Number	41552-82-3^Y
3D model (JSmol)	Interactive image
ChemSpider	571479^N
PubChem CID	657378
UNII	7LG47VG1ID^Y
CompTox Dashboard (EPA)	DTXSID80961807
InChI InChI=1S/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1^N Key: SQMWSBKSHWARHU-SDBHATRESA-N^N InChI=1/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1 Key: SQMWSBKSHWARHU-SDBHATREBV
SMILES C1CCC(C1)NC2=NC=NC3=C2N=CN3[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
Properties
Chemical formula	C₁₅H₂₁N₅O₄
Molar mass	335.364 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

References

[1]
Williams M, Braunwalder A, Erickson TJ (February 1986). "Evaluation of the binding of the A-1 selective adenosine radioligand, cyclopentyladenosine (CPA), to rat brain tissue". Naunyn-Schmiedeberg's Archives of Pharmacology. 332 (2): 179–183. doi:10.1007/BF00511410. PMID 3703020. S2CID 10740635.
[2]
Coffin VL, Spealman RD (April 1987). "Behavioral and cardiovascular effects of analogs of adenosine in cynomolgus monkeys". The Journal of Pharmacology and Experimental Therapeutics. 241 (1): 76–83. PMID 3572798.
[3]
Zablocki JA, Wu L, Shryock J, Belardinelli L (2004). "Partial A(1) adenosine receptor agonists from a molecular perspective and their potential use as chronic ventricular rate control agents during atrial fibrillation (AF)". Current Topics in Medicinal Chemistry. 4 (8): 839–854. doi:10.2174/1568026043450998. PMID 15078215.
[4]
Hutchinson SA, Scammells PJ (2004). "A(1) adenosine receptor agonists: medicinal chemistry and therapeutic potential". Current Pharmaceutical Design. 10 (17): 2021–2039. doi:10.2174/1381612043384204. PMID 15279543.
[5]
Elzein E, Kalla R, Li X, Perry T, Marquart T, Micklatcher M, Li Y, Wu Y, Zeng D, Zablocki J (January 2007). "N6-Cycloalkyl-2-substituted adenosine derivatives as selective, high affinity adenosine A1 receptor agonists". Bioorganic & Medicinal Chemistry Letters. 17 (1): 161–166. doi:10.1016/j.bmcl.2006.09.065. PMID 17045477.
[6]
Elzein E, Zablocki J (December 2008). "A1 adenosine receptor agonists and their potential therapeutic applications". Expert Opinion on Investigational Drugs. 17 (12): 1901–1910. doi:10.1517/13543780802497284. PMID 19012505. S2CID 74182151.
[7]
Franchetti P, Cappellacci L, Vita P, Petrelli R, Lavecchia A, Kachler S, Klotz KN, Marabese I, Luongo L, Maione S, Grifantini M (April 2009). "N6-Cycloalkyl- and N6-bicycloalkyl-C5'(C2')-modified adenosine derivatives as high-affinity and selective agonists at the human A1 adenosine receptor with antinociceptive effects in mice". Journal of Medicinal Chemistry. 52 (8): 2393–2406. doi:10.1021/jm801456g. PMID 19317449.

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N6-Cyclopentyladenosine

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