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ChemicalBook--->CAS DataBase List--->1337962-47-6

1337962-47-6

1337962-47-6 Structure

1337962-47-6 Structure
IdentificationBack Directory
[Name]

5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine
[CAS]

1337962-47-6
[Synonyms]

EOS-62029
Taminadenant
PBF-509,Taminadenant
5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine
4-Pyrimidinamine, 5-bromo-2,6-di-1H-pyrazol-1-yl-
5-bromo-2,6-di-(1H-pyrazol-1-yl)pyrimidine-4-amine
PBF509,PBF-509,P1 receptor,antitumor,tremor,Taminadenant,hemiparkinsonism,NIR-178,including catalepsy,PBF 509,Adenosine Receptor,inhibit,NIR 178,NIR178,Inhibitor,movement disorders
[Molecular Formula]

C10H8BrN7
[MDL Number]

MFCD30489281
[MOL File]

1337962-47-6.mol
[Molecular Weight]

306.12
Chemical PropertiesBack Directory
[Boiling point ]

574.9±60.0 °C(Predicted)
[density ]

1.93±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO : 125 mg/mL (408.34 mM; Need ultrasonic)
[form ]

Solid
[pka]

-0.39±0.10(Predicted)
[color ]

White to off-white
[InChI]

InChI=1S/C10H8BrN7/c11-7-8(12)15-10(18-6-2-4-14-18)16-9(7)17-5-1-3-13-17/h1-6H,(H2,12,15,16)
[InChIKey]

ATFXVNUWQOXRRU-UHFFFAOYSA-N
[SMILES]

BrC1=C(N=C(N2N=CC=C2)N=C1N1N=CC=C1)N
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Uses]

Taminadenant (NIR178; PBF509) is a highly potent and orally active adenosine A2A receptor (A2AR) antagonist. Taminadenant can antagonize A2AR agonist-mediated cAMP accumulation and impedance responses with KB values of 72.8 nM and 8.2 nM, respectively. Taminadenant reverses motor impairments in several rat models of movement disorders, including catalepsy, tremor, and hemiparkinsonism. Taminadenant can also inhibit tumor growth when combined with Spartalizumab.html" class="link-product" target="_blank">Spartalizumab (HY-P9972). Taminadenant reactivate the antitumor immune response[1][2].
[Synthesis]

Pyrazole

288-13-1

5-BROMO-6-CHLORO-2-(1H-PYRAZOL-1-YL)PYRIMIDIN-4-AMINE(WXG02982)

1337962-43-2

5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine

1337962-47-6

General procedure for the synthesis of 5-bromo-2,6-bis(1H-pyrazol-1-yl)pyrimidin-4-amine from pyrazole and 5-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amine: to a 3 mL DMF solution containing 0.15 g (0.55 mmol) of 5-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amine (Intermediate 5). 0.11 g (1.64 mmol) of 1H-pyrazole and 0.18 g (0.55 mmol) of cesium carbonate were added sequentially. The reaction mixture was stirred at 85°C for 24 hours. After completion of the reaction, the solvent DMF was removed by distillation under reduced pressure. the crude product was washed with water and dried to give 0.13 g (77% yield) of the target compound.1H NMR (300 MHz, DMSO-d6) δ: 6.57 (dd, 1H), 6.60 (dd, 1H), 7.52 (s, 1H), 7.81 (d, 1H), 7.87 (d, 1H) , 8.41 (s, 1H), 8.51 (d, 1H), 8.60 (d, 1H).

[in vivo]

Taminadenant (PBF509) (0.3, 3, 7.5, 10, or 30 mg/kg; p.o.; single dosage) attenuates the cataleptic effects of Haloperidol, attenuates pilocarpine-induced tremulous jaw movement, enhances the effects of L-DOPA, shows a robust antiparkinsonian activity and displays antidyskinetic efficacy[1].

Animal Model:Sprague-Dawley rats (240-250 g; induced catalepsy by s.c. with 1 mg/kg Haloperidol (HY-14538))[1]
Dosage:3, 10, or 30 mg/kg
Administration:p.o.; single dosage
Result:Dose-dependently attenuated the cataleptic effects of Haloperidol when administered 1 h after Haloperidol injection.
Animal Model:Sprague-Dawley rats (240-250 g; induced tremulous jaw movement by s.c. with 1 mg/kg Pilocarpine (HY-B0726A))[1]
Dosage:0.3, 3, or 7.5 mg/kg
Administration:p.o.; single dosage
Result:Dose-dependently attenuated pilocarpine-induced tremulous jaw movement, being effective at the lowest dose tested.
Animal Model:Sprague-Dawley rats (240-250 g; induced hemiparkinsonian by unilateral injection of 6-OHDA (HY-B1081) in the medial forebrain bundle)[1]
Dosage:0.3 and 3 mg/kg
Administration:p.o.; single dosage
Result:Enhanced the effects of L-DOPA with a minimum efficacious dose (MED) of 3 mg/kg p.o..
Animal Model:Sprague-Dawley rats (240-250 g; induced dyskinesias by i.p. 4 mg/kg L-DOPA (HY-N0304) for 14 days and i.p. 15 mg/kg Benserazide hydrochloride (HY-B0404A))[1]
Dosage:0.3 or 3 mg/kg
Administration:p.o.; single dosage
Result:Showed a robust antiparkinsonian activity and displayed antidyskinetic efficacy.
[References]

[1] Nú?ez F, et al. PBF509, an Adenosine A2A Receptor Antagonist With Efficacy in Rodent Models of Movement Disorders. Front Pharmacol. 2018 Oct 19;9:1200. DOI:10.3389/fphar.2018.01200
[2] Chiappori AA, et al. Phase I Study of Taminadenant (PBF509/NIR178), an Adenosine 2A Receptor Antagonist, with or without Spartalizumab (PDR001), in Patients with Advanced Non-Small Cell Lung Cancer. Clin Cancer Res. 2022 Jun 1;28(11):2313-2320. DOI:10.1158/1078-0432.CCR-21-2742
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