| Identification | Back Directory | [Name]
BAY 60-6583 | [CAS]
910487-58-0 | [Synonyms]
BAY 60-6583
2-[[6-Amino-3,5-dicyano-4-[4-(cyclopropylmethoxy)phenyl]-2-pyridinyl]thio]-acetamide
Acetamide, 2-[[6-amino-3,5-dicyano-4-[4-(cyclopropylmethoxy)phenyl]-2-pyridinyl]thio]- | [Molecular Formula]
C19H17N5O2S | [MDL Number]
MFCD22683833 | [MOL File]
910487-58-0.mol | [Molecular Weight]
379.44 |
| Chemical Properties | Back Directory | [Boiling point ]
684.8±55.0 °C(Predicted) | [density ]
1.43±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO | [form ]
powder | [pka]
14.98±0.40(Predicted) | [color ]
white to beige | [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) | [InChIKey]
ZTYHZMAZUWOXNC-UHFFFAOYSA-N | [SMILES]
NC1=C(C#N)C(C2=CC=C(OCC3CC3)C=C2)=C(C#N)C(SCC(N)=O)=N1 |
| Hazard Information | Back Directory | [Uses]
BAY 60-6583 is a potent and selective adenosine A2B receptor agonist. BAY 60-6583 shows protective effects against ischemia in both the heart and kidney in animal models. BAY 60-6583 is also a useful therapeutic drug in the treatment of acute lung injury. | [Definition]
ChEBI: A member of the class of cyanopyridines that is 6-amino-3,5-dicyano-4-(4-hydroxyphenyl)-2-sulfanylpyridine in which the hydroxy and sulfanyl hydrogens are replaced by cyclopropylmethyl and carboxamidomethyl groups respectively. | [Biological Activity]
bay 60-6583 is a selective and potent agonist of adenosine a2b receptor with ec50 value of 3 nm [1].the adenosine a2b receptor is a g-protein coupled adenosine receptor and is activated by high concentrations adenosine. the adenosine a2b receptor plays an important role in anti-inflammatory response and pre/postconditioning cardioprotective [1].bay 60-6583 is a potent adenosine a2b receptor agonist. in cho cells, bay 60-6583 showed ec50 values of >10000, >10000 and 3 nm respectively for recombinant human a1, a2a and a2b ars [1]. in beas-2b human airway epithelial cells transfected with glucocorticoid response element (gre) reporter and camp-response element (cre), bay 60-6583 increased gre- and cre-dependent transcription mediated by adenosine a2b receptor that was associated with camp formation. also, bay 60-6583 increased the expression of cd200, crispld2 and socs3, which suppressed the release of proinflammatory mediator [2]. in macrophages derived from arterial injury mice, bay 60-6583 increased the expression of a2bar, which then inhibited the released of tumor necrosis factor ɑ (tnf-ɑ) that promoting inflammatory response [3].in a myocardial ischaemic injury rabbit model, bay 60-6583 (100 mcg/kg) reduced the infarction area [1]. | [in vivo]
BAY 60-6583 (intravenous injection; 100 mcg/kg) reduces the infarction area just prior to reperfusion in ischaemic rabbit hearts[1].
BAY 60-6583 (intraperitoneal injection; 2 mg/kg) attenuates LPS-induced lung injury, pre-treatment with this compound can significantly decrease LPS-increased IL-6 levels in WT-mice, In contrast, BAY 60-6583 treatment is ineffective in abrogating these inflammatory parameters in A2BAR mice[2].
BAY 60-6583 (intratumoral administration) causes a significant increase in tumor-infiltrating MDSCs, it does not affect neither their ability to suppress T-cell proliferation nor their degree of maturation, it also stimulates the production of IL-10 and CCL2 in the tumor tissue[5]. | Animal Model: | ?A2BAR?/? ?mice on a C57BL/6J mice[1] | | Dosage: | 2 mg/kg | | Administration: | Intraperitoneal?injection; 2 mg/kg | | Result: | Demonstrated attenuation of lung inflammation and pulmonary edema in wild-type but not in gene-targeted mice for the A2BAR. |
| [storage]
Store at +4°C | [References]
[1]. baraldi pg, tabrizi ma, fruttarolo f, et al. recent improvements in the development of a(2b) adenosine receptor agonists. purinergic signal, 2008, 4(4): 287-303.
[2]. greer s, page cw, joshi t, et al. concurrent agonism of adenosine a2b and glucocorticoid receptors in human airway epithelial cells cooperatively induces genes with anti-inflammatory potential: a novel approach to treat chronic obstructive pulmonary disease. j pharmacol exp ther, 2013, 346(3): 473-485.
[3]. chen h, yang d, carroll sh, et al. activation of the macrophage a2b adenosine receptor regulates tumor necrosis factor-alpha levels following vascular injury. exp hematol, 2009, 37(5): 533-538. |
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BOC Sciences
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1-631-485-4226; 16314854226 |
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https://www.bocsci.com |
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