BAY 60–6583

BAY 60–6583 is a selective adenosine A2B receptor agonist.[1] It has been shown to provide protection from ischemia (lack of oxygen due to blocked blood supply) in both the heart and kidney of test animals,[2][3] and has also been shown to be beneficial in treatment of acute lung and brain injury,[4][5] as well as claimed anti-aging and anti-obesity effects,[6] showing a range of potential applications for selective A2B agonists.

BAY 60–6583
Names
Preferred IUPAC name
2-({6-Amino-3,5-dicyano-4-[4-(cyclopropylmethoxy)phenyl]pyridin-2-yl}sulfanyl)acetamide
Other names
BAY 60–6583
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C19H17N5O2S/c20-7-14-17(12-3-5-13(6-4-12)26-9-11-1-2-11)15(8-21)19(24-18(14)23)27-10-16(22)25/h3-6,11H,1-2,9-10H2,(H2,22,25)(H2,23,24)
    Key: ZTYHZMAZUWOXNC-UHFFFAOYSA-N
  • InChI=1/C19H17N5O2S/c20-7-14-17(12-3-5-13(6-4-12)26-9-11-1-2-11)15(8-21)19(24-18(14)23)27-10-16(22)25/h3-6,11H,1-2,9-10H2,(H2,22,25)(H2,23,24)
    Key: ZTYHZMAZUWOXNC-UHFFFAOYAY
SMILES
  • N#Cc1c(SCC(N)=O)nc(N)c(C#N)c1-c3ccc(cc3)OCC2CC2
Properties
Chemical formula
 C19H17N5O2S
Molar mass 379.435
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Baraldi PG, Tabrizi MA, Fruttarolo F, Romagnoli R, Preti D (December 2008). "Recent improvements in the development of A(2B) adenosine receptor agonists". Purinergic Signalling. 4 (4): 287–303. doi:10.1007/s11302-008-9097-z. PMC 2583210. PMID 18443746.
  2. Eckle T, Krahn T, Grenz A, Köhler D, Mittelbronn M, Ledent C, et al. (March 2007). "Cardioprotection by ecto-5'-nucleotidase (CD73) and A2B adenosine receptors". Circulation. 115 (12): 1581–90. doi:10.1161/CIRCULATIONAHA.106.669697. PMID 17353435.
  3. Grenz A, Osswald H, Eckle T, Yang D, Zhang H, Tran ZV, et al. (June 2008). "The reno-vascular A2B adenosine receptor protects the kidney from ischemia". PLoS Medicine. 5 (6): e137. doi:10.1371/journal.pmed.0050137. PMC 2504049. PMID 18578565.
  4. Eckle T, Grenz A, Laucher S, Eltzschig HK (October 2008). "A2B adenosine receptor signaling attenuates acute lung injury by enhancing alveolar fluid clearance in mice". The Journal of Clinical Investigation. 118 (10): 3301–15. doi:10.1172/JCI34203. PMID 18787641.
  5. Li Q, Han X, Lan X, Hong X, Li Q, Gao Y, et al. (December 2017). "Inhibition of tPA-induced hemorrhagic transformation involves adenosine A2b receptor activation after cerebral ischemia". Neurobiology of Disease. 108: 173–182. doi:10.1016/j.nbd.2017.08.011. PMC 5675803. PMID 28830843.
  6. Gnad T, Navarro G, Lahesmaa M, Reverte-Salisa L, Copperi F, Cordomi A, et al. (July 2020). "Adenosine/A2B Receptor Signaling Ameliorates the Effects of Aging and Counteracts Obesity". Cell Metabolism. 32 (1): 56–70.e7. doi:10.1016/j.cmet.2020.06.006. PMC 7437516. PMID 32589947.


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