ZM 241385
- Product Name
- ZM 241385
- CAS No.
- 139180-30-6
- Chemical Name
- ZM 241385
- Synonyms
- CS-2353;ZM 241385;ZM241385, 10 mM in DMSO;ZM 241385, A2A antagonist;ZM 241385; ZM241385; ZM-241385;Adenosine A2A Receptor Antagonist I, ZM 241385;4-(2-[7-AMINO-2-(2-FURYL)[1,2,4]TRIAZOLO[2,3-A][1,3,5]TRIAZIN-5-YLAMINO]ETHYL)PHENO;4-(2-[7-AMINO-2-(2-FURYL)[1,2,4]TRIAZOLO[2,3-A][1,3,5]TRIAZIN-5-YLAMINO]ETHYL)PHENOL;4-(2-(7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)ethyl)phenol;Phenol, 4-[2-[[7-amino-2-(2-furanyl)[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl]amino]ethyl]-
- CBNumber
- CB4121732
- Molecular Formula
- C16H15N7O2
- Formula Weight
- 337.34
- MOL File
- 139180-30-6.mol
ZM 241385 Property
- 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
N-Bromosuccinimide Price
- Product number
- Z0153
- Product name
- ZM 241385
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $105.45
- Updated
- 2025/07/31
- Product number
- Z0153
- Product name
- ZM 241385
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $449
- Updated
- 2025/07/31
- Product number
- 119149
- Product name
- Adenosine A2A Receptor Antagonist I, ZM 241385 - CAS 139180-30-6 - Calbiochem
- Purity
- A highly potent, selective, non-xanthine adenosine A2A receptor antagonist (Ki = 800 pM for human adenosine A2AR stably expressed in HEK-293 cells).
- Packaging
- 5MG
- Price
- $136
- Updated
- 2025/07/31
- Product number
- Z0042
- Product name
- ZM 241385
- Packaging
- 10MG
- Price
- $192
- Updated
- 2025/07/31
- Product number
- 20447
- Product name
- ZM 241385
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
ZM 241385 Chemical Properties,Usage,Production
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
51-67-2
139181-28-5
139180-30-6
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
ZM 241385 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from ZM 241385 manufacturers
- Product
- ZM241385 139180-30-6
- Price
- US $100.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 100KG
- Release date
- 2021-09-13
- Product
- ZM241385 139180-30-6
- Price
- US $100.00/Kg/Bag
- Min. Order
- 1Kg/Bag
- Purity
- 99%
- Supply Ability
- 10kg
- Release date
- 2021-09-15
- Product
- ZM 241385 139180-30-6
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100KG
- Release date
- 2019-12-20