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Merck
CN

SML3089

MRS-1706

≥98% (HPLC)

Synonym(s):

8-[4-[((4-Acetylphenyl)carbamoylmethyl)oxy]phenyl]-1,3-di(n-propyl)xanthine, MRS 1706, MRS1706, N-(4-Acetylphenyl)-2-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)phenoxy)acetamide, N-(4-Acetylphenyl)-2-[4-(2,3,6,9-tetrahydro-2,6-dioxo-1,3-dipropyl-1H-purin-8-yl)phenoxy]acetamide

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About This Item

Empirical Formula (Hill Notation):
C27H29N5O5
CAS Number:
264622-53-9
Molecular Weight:
503.55
NACRES:
NA.77
UNSPSC Code:
12352200

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InChI

1S/C27H29N5O5/c1-4-14-31-25-23(26(35)32(15-5-2)27(31)36)29-24(30-25)19-8-12-21(13-9-19)37-16-22(34)28-20-10-6-18(7-11-20)17(3)33/h6-13H,4-5,14-16H2,1-3H3,(H,28,34)(H,29,30)

InChI key

ZKUCFFYOQOJLGT-UHFFFAOYSA-N

SMILES string

O=C(COC1=CC=C(C=C1)C2=NC3=C(N2)N(C(N(C3=O)CCC)=O)CCC)NC4=CC=C(C=C4)C(C)=O

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

High-affinity, potent and selective adenosine 2B receptor (A2B) antagonist/inverse agonist.
MRS-1706 is a high-affinity, potent and selective adenosine 2B receptor (A2B) antagonist/inverse agonist (human A1/A2A/A2B/A3 Ki = 157/112/1.39/230 nM; rat A1/A2A Ki = 37.6/548 nM). MRS-1706 (20 nM), but not the A2A antagonist SCH 58261 (20 nM), completely blocks the enhancement of electrically evoked tritium overflow from isolated rat tail artery by 10 μM adenosine receptor agonist NECA in the presence of 30 nM A1 antagonist DPCPX.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000137091
0000137092
0000135076

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Y C Kim et al.
Journal of medicinal chemistry, 43(6), 1165-1172 (2000-03-29)
No highly selective antagonists of the A(2B) adenosine receptor (AR) have been reported; however such antagonists have therapeutic potential as antiasthmatic agents. Here we report the synthesis of potent and selective A(2B) receptor antagonists. The structure-activity relationships (SAR) of 8-phenyl-1
The A2B Adenosine Receptor Modulates the Epithelial- Mesenchymal Transition through the Balance of cAMP/PKA and MAPK/ERK Pathway Activation in Human Epithelial Lung Cells.
Giacomelli, et al.
Frontiers in Pharmacology, 9, 54-54 (2020)
Fabio Morandi et al.
Journal of immunology (Baltimore, Md. : 1950), 202(3), 724-735 (2018-12-28)
This study investigates the mechanism(s) underlying the immunoregulatory activities of placenta-derived human amnion epithelial cells (hAEC). The working hypothesis is that NAD+ and ATP, along with ectoenzymes involved in their metabolism, play a significant role in hAEC-mediated immune regulation. Proof
Qilan Li et al.
The Journal of pharmacology and experimental therapeutics, 320(2), 637-645 (2006-11-02)
The human adenosine A(2B) receptor belongs to class A G protein-coupled receptors (GPCRs). In our previous work, constitutively active mutant (CAM) human adenosine A(2B) receptors were identified from a random mutation bank. In the current study, three known A(2B) receptor
Ecto-5'-nucleotidase (CD73) attenuates inflammation after spinal cord injury by promoting macrophages/microglia M2 polarization in mice.
Xu, et al.
Journal of Neuroinflammation, 15, 155-155 (2019)
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