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Merck

S6451

Sigma-Aldrich

SCH-442416

≥98% (HPLC)

Sinónimos:

2-(2-Furanyl)-7-[3-(4-methoxyphenyl)propyl]-7H-pyrazolo [4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine; 5-amino-7-(3-(4-methoxyphenyl)propyl)-2-(2 furyl)pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine; 5-Amino-7-[3-(4-methoxy)phenylpropyl]-2-(2-furyl)-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine

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About This Item

Fórmula empírica (notación de Hill):
C20H19N7O2
Número de CAS:
Peso molecular:
389.41
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

light tan to tan

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

COc1ccc(CCCn2ncc3c2nc(N)n4nc(nc34)-c5ccco5)cc1

InChI

1S/C20H19N7O2/c1-28-14-8-6-13(7-9-14)4-2-10-26-18-15(12-22-26)19-23-17(16-5-3-11-29-16)25-27(19)20(21)24-18/h3,5-9,11-12H,2,4,10H2,1H3,(H2,21,24)

InChI key

AEULVFLPCJOBCE-UHFFFAOYSA-N

Application

SCH-442416 has been used:
  • as a selective adenosine A2A antagonist to study its effects on cyclic adenosine monophosphate (cAMP) production in T/C-28a2 chondrocytes or hFOB 1.19 osteoblasts 
  • as a presynaptic A2A receptor antagonists to study its effects on receptor blockade on δ9-Tetrahydrocannabinol (THC) self-administration in squirrel monkeys
  • as a presynaptic A2A receptor antagonists to study its effects on cocaine-induced locomotion and cocaine-seeking in mice

Biochem/physiol Actions

SCH-442416 potent and selective Adenosine A2a antagonist. SCH-442416 is >10,000-fold selective for A2a compared to other adensosine receptors.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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Effects of adenosine A 2A receptor antagonists on cocaine-induced locomotion and cocaine seeking
Haynes N S, et al.
Psychopharmacology, 236(2), 699-708 (2019)
Ying Wang et al.
ACS chemical neuroscience, 10(4), 1941-1949 (2018-09-27)
Adenosine is an endogenous neuroprotectant that modulates vasodilation in the central nervous system. Oxygen changes occur when there is an increase in local cerebral blood flow and thus are a measure of vasodilation. Transient oxygen events following rapid adenosine events
Takahiro Matsuya et al.
Journal of pharmacological sciences, 103(3), 329-332 (2007-03-08)
In this study, we examined the combination effects of L-DOPA and adenosine receptor antagonists on rotational behaviors in a hemi-Parkinsonian mouse model induced by unilateral 6-hydroxydopamine (6-OHDA) injection. The adenosine A(2A) antagonist SCH-58261, but not the A(1)-receptor antagonist 8-cyclopentyl-1,3-dipropylxanthine or
Carmen Methner et al.
American journal of physiology. Heart and circulatory physiology, 299(4), H1262-H1264 (2010-08-17)
Pre- and postconditioning depend on the activation of adenosine receptors (ARs) at the end of the index ischemia. The aim of this study was to determine which receptor subtypes must be activated. In situ mouse hearts underwent 30 min of
Natnaree Siriwon et al.
Cancer immunology research, 6(7), 812-824 (2018-05-04)
One limiting factor of CAR T-cell therapy for treatment of solid cancers is the suppressive tumor microenvironment (TME), which inactivates the function of tumor-infiltrating lymphocytes (TIL) through the production of immunosuppressive molecules, such as adenosine. Adenosine inhibits the function of

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