PSB-10

PSB-10
Clinical data
Other names	PSB-10
Identifiers
	IUPAC name (8R)-ethyl-4-methyl-2-(2,3,5-trichlorophenyl)-4,5,7,8-tetrahydro-1H-imidazo[2,1-i]purin-5-one;
CAS Number	439902-54-2 ; HCl: 591771-91-4 ;
PubChem CID	10318703;
IUPHAR/BPS	5619;
ChemSpider	8494167 ;
UNII	2DRZ23E4F7; HCl: C2R36CZP9N ;
ChEMBL	ChEMBL1562432 ;
Chemical and physical data
Formula	C16H14Cl3N5O
Molar mass	398.67 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc2cc(Cl)cc(c2Cl)C(=N3)NC1C3N(C)C(=O)N4C1=NC(C4)CC;
	InChI InChI=1S/C16H14Cl3N5O/c1-3-8-6-24-15(20-8)12-14(23(2)16(24)25)22-13(21-12)9-4-7(17)5-10(18)11(9)19/h4-5,8H,3,6H2,1-2H3,(H,21,22)/t8-/m1/s1 ; Key:YYDHUJWLNPIBDS-MRVPVSSYSA-N ;
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PSB-10 is a drug which acts as a selective antagonist^[1] for the adenosine A₃ receptor (k_i value at human A₃ receptor is 0.44 nM), with high selectivity over the other three adenosine receptor subtypes (k_i values at human A₁, A_2A and A_2B receptors are 4.1, 3.3 and 30 μM). Further pharmacological experiments in a [³⁵S]GTPγS binding assay using hA₃-CHO-cells indicated that PSB-10 acts as an inverse agonist (IC₅₀ = 4 nM). It has been shown to produce antiinflammatory effects in animal studies.^[2] Simple xanthine derivatives such as caffeine and DPCPX have generally low affinity for the A₃ subtype and must be extended by expanding the ring system and adding an aromatic group to give high A₃ affinity and selectivity.^[3] The affinity towards adenosine A₃ subtype was measured against the radioligand PSB-11.^[4]

References

^ Ozola V, Thorand M, Diekmann M, Qurishi R, Schumacher B, Jacobson KA, Müller CE (2003). "2-Phenylimidazo[2,1-i]purin-5-ones: structure-activity relationships and characterization of potent and selective inverse agonists at Human A3 adenosine receptors". Bioorg Med Chem. 11 (3): 347–56. doi:10.1016/S0968-0896(02)00456-X. PMC 8376400. PMID 12517430.
^ Bilkei-Gorzo A, Abo-Salem OM, Hayallah AM, Michel K, Müller CE, Zimmer A (March 2008). "Adenosine receptor subtype-selective antagonists in inflammation and hyperalgesia". Naunyn-Schmiedeberg's Archives of Pharmacology. 377 (1): 65–76. doi:10.1007/s00210-007-0252-9. PMID 18188542. S2CID 6110998.
^ Müller CE (2003). "Medicinal chemistry of adenosine A3 receptor ligands". Current Topics in Medicinal Chemistry. 3 (4): 445–62. doi:10.2174/1568026033392174. PMID 12570761. Archived from the original on April 14, 2013. Retrieved April 28, 2020.{{cite journal}}: CS1 maint: unfit URL (link)
^ Müller CE, Diekmann M, Thorand M, Ozola V (2002). "[(3)H]8-Ethyl-4-methyl-2-phenyl-(8R)-4,5,7,8-tetrahydro-1H-imidazo[2,1-i]-purin-5-one ([(3)H]PSB-11), a novel high-affinity antagonist radioligand for human A(3) adenosine receptors". Bioorg Med Chem Lett. 12 (3): 501–3. doi:10.1016/S0960-894X(01)00785-5. PMID 11814828.

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[pmid12517430-1] Ozola V, Thorand M, Diekmann M, Qurishi R, Schumacher B, Jacobson KA, Müller CE (2003). "2-Phenylimidazo[2,1-i]purin-5-ones: structure-activity relationships and characterization of potent and selective inverse agonists at Human A3 adenosine receptors". Bioorg Med Chem. 11 (3): 347–56. doi:10.1016/S0968-0896(02)00456-X. PMC 8376400. PMID 12517430.

[pmid18188542-2] Bilkei-Gorzo A, Abo-Salem OM, Hayallah AM, Michel K, Müller CE, Zimmer A (March 2008). "Adenosine receptor subtype-selective antagonists in inflammation and hyperalgesia". Naunyn-Schmiedeberg's Archives of Pharmacology. 377 (1): 65–76. doi:10.1007/s00210-007-0252-9. PMID 18188542. S2CID 6110998.

[pmid12570761-3] Müller CE (2003). "Medicinal chemistry of adenosine A3 receptor ligands". Current Topics in Medicinal Chemistry. 3 (4): 445–62. doi:10.2174/1568026033392174. PMID 12570761. Archived from the original on April 14, 2013. Retrieved April 28, 2020.{{cite journal}}: CS1 maint: unfit URL (link)

[pmid11814828-4] Müller CE, Diekmann M, Thorand M, Ozola V (2002). "[(3)H]8-Ethyl-4-methyl-2-phenyl-(8R)-4,5,7,8-tetrahydro-1H-imidazo[2,1-i]-purin-5-one ([(3)H]PSB-11), a novel high-affinity antagonist radioligand for human A(3) adenosine receptors". Bioorg Med Chem Lett. 12 (3): 501–3. doi:10.1016/S0960-894X(01)00785-5. PMID 11814828.

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