BAY 60–6583

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	910487-58-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	9892551;
IUPHAR/BPS	3289;
PubChem CID	11717831;
UNII	UAT5472LHH ;
CompTox Dashboard (EPA)	DTXSID301028169 ;
	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

BAY 60–6583 is a selective adenosine A_2B receptor agonist. 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, and has also been shown to be beneficial in treatment of acute lung and brain injury, as well as claimed anti-aging and anti-obesity effects, showing a range of potential applications for selective A_2B agonists.

References

↑ 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.
↑ 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.
↑ 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.
↑ 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. PMC 2532979. PMID 18787641.
↑ 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.
↑ 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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[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. PMC 2532979. 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.