Reversine
Grundinformationen
- CAS
656820-32-5- Standard-SMILES
c1nc2nc(Nc3ccc(N4CCOCC4)cc3)nc(NC3CCCCC3)c2[nH]1- InChIKey
ZFLJHSQHILSNCM-UHFFFAOYSA-N- Summenformel
- C21H27N7O
- Durchschnittliche Molmasse
- 393,5 g/mol
- Monoisotopische Masse
- 393,22770851
Namen und Bezeichner
- Bevorzugter Name
- Reversine
- IUPAC
- 6-N-cyclohexyl-2-N-(4-morpholin-4-ylphenyl)-7H-purine-2,6-diamine
- Englischer Name
- REVERSINE
- Summenformel
- C21H27N7O
- Molmasse
- 393.49
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
656820-32-5- PubChem CID
- 210332
- DTXSID
DTXSID8041113- ChEMBL
CHEMBL188343- ChEBI
CHEBI:70723- UNII
- Z499CLJ023
- EC Number
- 636-256-0
- Nikkaji
- J2.006.667I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,9
- Polarare Oberfläche (TPSA)
- 91 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 503
Physikochemische Eigenschaften
- Schmelzpunkt
- 305 ℃ · 305℃ (decomposition)
- Siedepunkt
- 736.4 · 736.4±70.0 °C(Predicted)
- Dichte
- 1.343 · 1.343±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 7 mg/mL, · DMSO: 7 mg/mL, soluble
- Aggregatzustand
- solid
- pka
- 10.51 · 10.51±0.10(Predicted)
- Farbe
- Off-white
- Stabilität
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months
- InChI
- 1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27)
- InChIKey
- ZFLJHSQHILSNCM-UHFFFAOYSA-N
- SMILES
- C1CCC(CC1)Nc2nc(Nc3ccc(cc3)N4CCOCC4)nc5nc[nH]c25
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Sicherheitsdaten
- wgk
- 3
- risk_code
- 22
- hazard_code
- Xn
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungReversine is a 2,6-disubstituted purine derivative that was originally found to induce dedifferentiation of C2C12 culture myoblast cells into stem cell progenitors when used at a concentration of 5 μM for four days. Depending on cell type, reversine promotes either differentiation or dedifferentiation. For example, in NT2 neuronal and HL-60 human promyelocytic leukemia cells, it induces differentiation. It inhibits the Aurora A, B, and C kinases with IC50 values of 98-876 nM and acts as an antagonist at the adenosine A3 receptor with a Ki value of 0.66 μM. Reversine is also used for studies of chromosome segregation. It inhibits the mitotic spindle checkpoint enzyme MPS1 with IC50 values of 6 and 2.8 nM for its kinase domain and full-length version, respectively). Reversine induces autophagy in WRO human follicular thyroid cancer cells and decreases Akt/mTOR signaling.
VerwendenReversine acts as a potent human A3 adenosine receptor antagonist and pan-aurora A/B/C kinase inhibitor. Used for stem cell differentiation.
Anbieter100 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A member of the class of purines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by a [4-(morpholin-4-yl)phenyl]nitrilo group and a cyclohexylamino group, respectively.
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