M228

MRS 1220

Name: MRS 1220
Brand: SIGMA
Price: 304000 HUF

solid

Synonym(s):

9-Chloro-2-(2-furanyl)-5-((phenylacetyl)amino)-[1,2,4]triazolo[1,5-c]quinazoline

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5 MG

HUF 304,000.00

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₁₄ClN₅O₂

CAS Number:

183721-15-5

Molecular Weight:

403.82

NACRES:

NA.77

PubChem Substance ID:

24896720

UNSPSC Code:

12352209

MDL number:

MFCD01321046

Key Documents

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Product Name

MRS 1220, solid

InChI

1S/C21H14ClN5O2/c22-14-8-9-16-15(12-14)20-25-19(17-7-4-10-29-17)26-27(20)21(23-16)24-18(28)11-13-5-2-1-3-6-13/h1-10,12H,11H2,(H,23,24,28)

SMILES string

Clc1ccc2nc(NC(=O)Cc3ccccc3)n4nc(nc4c2c1)-c5ccco5

InChI key

TWWFAXQOKNBUCR-UHFFFAOYSA-N

form

solid

color

white

solubility

DMSO: 2 mg/mL
2-hydroxypropyl-β-cyclodextrin: insoluble
H₂O: insoluble
ethanol: insoluble

Quality Level

100

Gene Information

human ... ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

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Show Differences

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This Item	M7319	S4568	C199
Sigma-Aldrich M228 MRS 1220	Sigma-Aldrich M7319 ML 10302	Sigma-Aldrich S4568 SCH 58261	Sigma-Aldrich C199 CGS-15943
form solid	form solid	form solid	form solid
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
solubility DMSO: 2 mg/mL, H₂O: insoluble, 2-hydroxypropyl-β-cyclodextrin: insoluble, ethanol: insoluble	solubility DMSO: >20 mg/mL, H₂O: insoluble	solubility DMSO: soluble >10 mg/mL, H₂O: insoluble	solubility DMSO: >10 mg/mL, H₂O: insoluble
color white	color white to off-white	color off-white	color white
Gene Information human ... ADORA3(140) rat ... Adora1(29290), Adora2a(25369), Adora3(25370)	Gene Information rat ... Htr3a(79246), Htr4(25324)	Gene Information -	Gene Information human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140) rat ... Adora1(29290), Adora2a(25369), Adora2b(29316)

Biochem/physiol Actions

MRS1220 is a putative A3 adenosine receptor antagonist. MRS 1220 was found to be competitive in saturation binding studies using the agonist radioligand ¹²⁵I AB-MECA at cloned human brain A3 receptors expressed in HEK-293 cells. Antagonism was demonstrated in functional assays consisting of agonist-induced inhibition of adenylate cyclase and the stimulation of binding of ³⁵S guanosine 5′-O-(3-thiotriphosphate (³⁵S GTP-gamma-S) to the associated G-proteins. MRS 1220 and MRS 1191, with KB values of 1.7 and 92 nM, respectively, proved to be highly selective for human A3 receptor vs human A1 receptor-mediated effects on adenylate cyclase. In addition, MRS 1220 reversed the effect of A3 agonist-elicited inhibition of tumor necrosis factor-alpha formation in the human macrophage U-937 cell line, with an IC₅₀ value of 0.3 μM.

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

121K4604

090K4611

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The PI3K-NF-kappaB signal transduction pathway is involved in mediating the anti-inflammatory effect of IB-MECA in adjuvant-induced arthritis.

Pnina Fishman et al.

Arthritis research & therapy, 8(1), R33-R33 (2006-03-02)

The anti-inflammatory effect of adenosine was previously found to be mediated via activation of the A3 adenosine receptor (A3AR). The aim of the present study was to decipher the molecular mechanism involved with the inhibitory effect of IB-MECA, an A3AR

Naunyn-Schmiedeberg'S Archives of Pharmacology, 364, 225-234 (2000)

The antioxidant resveratrol acts as a non-selective adenosine receptor agonist.

A Sánchez-Melgar et al.

Free radical biology & medicine, 135, 261-273 (2019-03-23)

Resveratrol (RSV) is a natural polyphenolic antioxidant with a proven protective role in several human diseases involving oxidative stress, although the molecular mechanism underlying this effect remains unclear. The present work tried to elucidate the molecular mechanism of RSV's role

Derivatives of the triazoloquinazoline adenosine antagonist (CGS15943) are selective for the human A3 receptor subtype.

Y C Kim et al.

Journal of medicinal chemistry, 39(21), 4142-4148 (1996-10-11)

The adenosine antagonist 9-chloro-2-(2-furanyl)[1,2,4]triazolo[1,5-c]quinazolin-5-amine (CGS15943) binds to human A3 receptors with high affinity (Ki = 14 nM), while it lacks affinity at rat A3 receptors. Acylated derivatives of the 5-amino group and other modifications were prepared in an effort to

Pharmacological characterization of novel A3 adenosine receptor-selective antagonists.

K A Jacobson et al.

Neuropharmacology, 36(9), 1157-1165 (1997-11-19)

The effects of putative A3 adenosine receptor antagonists of three diverse chemical classes (the flavonoid MRS 1067, the 6-phenyl-1,4-dihydropyridines MRS 1097 and MRS 1191, and the triazoloquinazoline MRS 1220) were characterized in receptor binding and functional assays. MRS1067, MRS 1191

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MRS 1220