ZM 241385 Chemical Properties

Density 

1.59±0.1 g/cm3(Predicted)

storage temp. 

room temp

solubility 

DMSO: >15mg/mL

pka

10.03±0.15(Predicted)

form 

powder

color 

white to tan

InChI

InChI=1S/C16H15N7O2/c17-14-20-15(18-8-7-10-3-5-11(24)6-4-10)21-16-19-13(22-23(14)16)12-2-1-9-25-12/h1-6,9,24H,7-8H2,(H3,17,18,19,20,21,22)

InChIKey

PWTBZOIUWZOPFT-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(CCNC2N=C(N)N3N=C(C4=CC=CO4)N=C3N=2)C=C1

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

46

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

ZM 241385 Usage And Synthesis

Uses

ZM 241385 is a selective and potent Adenosine A2A-R antagonist.

Definition

ChEBI: 4-[2-[[7-amino-2-(2-furanyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl]amino]ethyl]phenol is a diamino-1,3,5-triazine.

Biochem/physiol Actions

ZM 241385 is a potent selective adenosine A2A antagonist. The A2A receptor plays a role in regulating myocardial oxygen consumption and coronary blood flow and is highly expressed in the brain, where it has important roles in the regulation of glutamate and dopamine release. ZM 241385 has neuroprotective effects and is being investigated for use in Parkinson′s and other neurodegenerative disorders.

Synthesis

A reaction was carried out in acetonitrile (25 mL) with p-hydroxyphenethylamine (tyramine, 490 mg, 3.75 mmol) and 2-(furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine (250 mg, 892 μmol). The reaction mixture was stirred at room temperature for 22 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was adsorbed through diatomaceous earth and purified using column chromatography (eluent: dichloromethane/methanol, 25:75, v/v). The target product grade was collected, evaporated to dryness and subsequently recrystallized from ethyl acetate to afford 4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol (100 mg, 33% yield) as a white solid, melting point: 229-231 °C (literature value: 225- 227°C). The product was analyzed and confirmed by 1H NMR, 13C NMR, high resolution mass spectrometry (HRMS) and high performance liquid chromatography (HPLC).1H NMR (400 MHz, d6-DMSO, 353 K) δ 8.91 (s, 1H), 7.92 (br s, 2H), 7.79 (m, 1H), 7.14 (br t, 1H), 7.04 (m, 3H) , 6.71 (m, 2H), 6.64 (dd, J = 3.3, 1.8 Hz, 1H), 3.49 (m, 2H), 2.78 (m, 2H).13C NMR (101 MHz, d6-DMSO) δ 161.1 (C), 159.0 (C), 155.9 (C), 155.4 (C), 150.1 (C), 146.1 (C), 146.1 (C), 146.1 (C), 146.1 (C), 146.1 (C), 146.1 (C). 146.1 (C), 144.1 (CH), 129.1 (CH), 115.0 (CH), 111.4 (CH), 111.2 (CH), 42.4 (CH2), 33.9 (CH2). HRMS (C16H15N7O2): Calculated value 338.1360 [M + H]+, measured value 338.1353. HPLC : tR 7.34 min, purity 98% (214 nm), 97% (254 nm).

storage

Room temperature

References

[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3427 - 3433
[2] Structural Chemistry, 2013, vol. 24, # 4, p. 1241 - 1251
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 2, p. 718 - 738
[4] Molecular Pharmacology, 1995, vol. 48, # 6, p. 970 - 974
[5] Patent: US5270311, 1993, A

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