| Identification | More | [Name]
4-Aminopyrazolo[3,4-d]pyrimidine | [CAS]
2380-63-4 | [Synonyms]
1H-PYRAZOLO[3,4-D]PYRIMIDIN-4-AMINE
1H-PYRAZOLO[3,4-D]PYRIMIDIN-4-YLAMINE
4-AMINO-1H-PYRAZOLO[3,4-D]PYRIMIDINE
4-AMINOPYRAZOLO[3,4-D]PYRIMIDINE
ADENINE ANTIMETABOLITE
TIMTEC-BB SBB004205
1H-Pyrazolo[3,4-d]pyrimidine, 4-amino-
4 APP
4-Aminopyrazole(3,4-d)pyrimidine
4-Aminopyrazolopyrimidine
4-app
4-d)pyrimidine,4-amino-1h-pyrazolo(
NSC 1393
nsc1393
Pyrazoloadenine
1H-Pyrazolo[3,4-d]pyrimidin-4-amine (9CI)
Adenine antimetabolite, Pyrazolo[3,4-d]pyrimidin-4-amin
Aminopurinol
4-Amino-1,2,5,7-tetraaza-1H-indene | [EINECS(EC#)]
219-174-6 | [Molecular Formula]
C5H5N5 | [MDL Number]
MFCD00005688 | [Molecular Weight]
135.13 | [MOL File]
2380-63-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Tan Solid | [Melting point ]
>325 °C(lit.)
| [Boiling point ]
238.81°C (rough estimate) | [density ]
1.3795 (rough estimate) | [refractive index ]
1.7000 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
soluble in DMSO | [form ]
powder to crystal | [pka]
12.12±0.20(Predicted) | [color ]
White to Orange to Green | [Water Solubility ]
Insoluble in water. | [BRN ]
5824 | [InChI]
1S/C5H5N5/c6-4-3-1-9-10-5(3)8-2-7-4/h1-2H,(H3,6,7,8,9,10) | [InChIKey]
LHCPRYRLDOSKHK-UHFFFAOYSA-N | [SMILES]
Nc1ncnc2[nH]ncc12 | [CAS DataBase Reference]
2380-63-4(CAS DataBase Reference) | [NIST Chemistry Reference]
1H-pyrazolo[3,4-d]pyrimidin-4-amine(2380-63-4) | [EPA Substance Registry System]
2380-63-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S22:Do not breathe dust . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
UR0717000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29335990 | [Storage Class]
6.1D - Non-combustible acute toxic Cat.3
toxic hazardous materials or hazardous materials causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | [Toxicity]
LD50 oral in rat: 141mg/kg |
| Hazard Information | Back Directory | [Description]
4-aminopyrazolo[3,4-d]pyrimidine (4-APP), the isomer of adenine with the five-membered ring in the pyrazole configuration, is by far the most potent inhibitor of both enzymatic reactions catalyzed by Stx1. It is also a new type of mTOR inhibitor. The 4-aminopyrazolo[3,4-d]pyrimidines, a well-characterized class of compounds for tyrosine kinase inhibition, were used as a Src inhibitor module that blocks the adenosine binding site[1-2]. | [Chemical Properties]
Light Tan Solid | [Uses]
4-Amino-1H-pyrazolo[3,4-d]pyrimidine decreases serum cholesterol markedly in rats. | [Hazard]
4-Aminopyrazolo[3,4-d]pyrimidine is harmful, irritating to the eyes and skin, and may cause respiratory irritation by inhalation. It is toxic if swallowed. | [Synthesis]
4-Chloro-1H-pyrazolo[3,4-d]pyrimidine (200 mg, 1.29 mmol) was used as starting material and dissolved in tetrahydrofuran (THF, 2.0 mL). Subsequently, ammonium hydroxide (2.0 mL) was added to this solution. The reaction mixture was stirred at 20 to 30 °C for 2 hours. After the reaction was completed, the mixture was concentrated. The concentrate was ground with acetonitrile (MeCN, 0.5 mL) and the product was subsequently collected by filtration to afford 4-aminopyrazolo[3,4-d]pyrimidine (37) as a red solid (100 mg, 57% yield). | [References]
[1] M Brigotti. “4-Aminopyrazolo[3,4-d]pyrimidine (4-APP) as a novel inhibitor of the RNA and DNA depurination induced by Shiga toxin 1.” Nucleic Acids Research 28 12 (2000): 2383–8.
[2] Ho Jin Lee. “Development of a 4-aminopyrazolo[3,4-d]pyrimidine-based dual IGF1R/Src inhibitor as a novel anticancer agent with minimal toxicity.” Molecular Cancer 17 1 (2018): 50.
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