N6-Cyclopentyladenosine

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 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 571479 ☒N
PubChem CID
  • 657378
UNII
  • 7LG47VG1ID checkY
CompTox Dashboard (EPA)
  • DTXSID80961807 Edit this at Wikidata
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
  • 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 checkY☒N ?)
Infobox references
Chemical compound

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]

See also

  • N6-Methyladenosine

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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Purine receptor modulators
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
See also: Receptor/signaling modulators


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