ChemicalBook--->CAS DataBase List--->305350-87-2

305350-87-2

305350-87-2 Structure

305350-87-2 Structure
IdentificationBack Directory
[Name]

SL 327
[CAS]

305350-87-2
[Synonyms]

SL 327
CS-1890
SL 327; SL-327
SL 327 USP/EP/BP
MEK Inhibitor VII
Mek-1/Mek-2 Inhibitor
SL327;SL-327;MEK-1/MEK-2 INHIBITOR
3-amino-3-(4-aminophenylthio)-2-(2-(trifluoromethyl)phenyl)acrylonitrile
(Z)-3-amino-3-(4-aminophenylthio)-2-(2-(trifluoromethyl)phenyl)acrylonitrile
α-[amino-(4-aminophenylthio)methylene)-2-(trifluoromethyl)phenylacetonitrile
α-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile
a-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile
ALPHA-[AMINO-(4-AMINOPHENYLTHIO)METHYLENE)-2-(TRIFLUOROMETHYL)PHENYLACETONITRILE
Benzeneacetonitrile, α-[amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)-
ALPHA-[AMINO[(4-AMINOPHENYL)THIO]METHYLENE]-2-(TRIFLUOROMETHYL)BENZENEACETONITRILE
(Z)-3-amino-3-(4-aminophenyl)sulfanyl-2-[2-(trifluoromethyl)phenyl]prop-2-enenitrile
(2Z)-3-amino-3-[(4-aminophenyl)sulfanyl]-2-[2-(trifluoromethyl)phenyl]prop-2-enenitrile
SL 327 alpha-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile
Z-AND E-ALPHA-(AMINO-((4-AMINOPHENYL)THIO)METHYLENE)-2-(TRIFLUOROMETHYL)BENZENEACETONITRILE
Z-EPSILON-T E-ALPHA-(AMINO-((4-AMINOPHENYL)THIO)METHYLENE)-2-(TRIFLUOROMETHYL)BENZENEACETONITRILE
alpha-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile SL 327
[Molecular Formula]

C16H12F3N3S
[MDL Number]

MFCD06411432
[MOL File]

305350-87-2.mol
[Molecular Weight]

335.35
Chemical PropertiesBack Directory
[Melting point ]

127-128.2 °C
[Boiling point ]

512.6±50.0 °C(Predicted)
[density ]

1.40
[storage temp. ]

2-8°C
[solubility ]

DMSO: 32 mg/mL
[form ]

solid
[pka]

3.42±0.10(Predicted)
[color ]

white
[InChI]

1S/C16H12F3N3S/c17-16(18,19)14-4-2-1-3-12(14)13(9-20)15(22)23-11-7-5-10(21)6-8-11/h1-8H,21-22H2/b15-13+
[InChIKey]

JLOXTZFYJNCPIS-FYWRMAATSA-N
[SMILES]

N\C(Sc1ccc(N)cc1)=C(\C#N)c2ccccc2C(F)(F)F
Safety DataBack Directory
[WGK Germany ]

3
[HS Code ]

2930909899
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

The dual specific threonine/tyrosine kinase MEK is a key component of the RAS/RAF/MEK/ERK signaling pathway that regulates a diverse array of cellular processes. SL 327 is an inhibitor of MEK1 and MEK2 (IC50s = 0.18 and 0.22 μM), the kinases upstream of ERK1/2. It inhibits ERK1, MKK/p38, MKK4, JNK, and PKC at much higher concentrations (IC50s = >50, 21, >100, >100, >10 μM, respectively). Since SL 327 rapidly passes the blood-brain barrier, it has been used to dissect the effect of RAS/RAF/MEK/ERK signaling pathway inhibition on behavior, including long-term memory, spatial learning, and fear/operant conditioning.
[Uses]

A selective inhibitor of MEK1 and MEK2 (IC50= 0.18 and 0.22 μM respectively). Displays neuroprotective effects against ischemic brain injury.
[Definition]

ChEBI: A nitrile that is acrylonitrile in which the hydrogen attached to the same carbon as the cyano group has been replaced by an o-(trifluoromethyl)phenyl group, while the remaining hydrogens of the ethenyl group have been replaced by amino and (4 aminophenyl)sulfanyl groups. The configuration of the double bond is not specified. It is an inhibitor of MEK1 and MEK2.
[Biological Activity]

Selective inhibitor of MEK1 and MEK2 (IC 50 values are 0.18 and 0.22 μ M respectively); blocks hippocampal LTP in vitro . Brain penetrant in vivo , blocking fear conditioning and learning in rats, and producing neuroprotection in mice, following systemic administration.
[Biochem/physiol Actions]

SL327 is a selective MEK1/2inhibitor (IC50 values are 0.18 and 0.22 μM for MEK1 and MEK2 respectively), which blocks hippocampal LTP in vitro. SL327 is a brain penetrant in vivo blocking fear conditioning and learning in rats, and producing neuroprotection in mice following systemic administration.
[storage]

+4°C (desiccate)
[References]

[1] P A SCHERLE. Regulation of cyclooxygenase-2 induction in the mouse uterus during decidualization. An event of early pregnancy.[J]. The Journal of Biological Chemistry, 2000, 275 47: 37086-37092. DOI: 10.1074/jbc.m006168200
[2] STEFANIA FASANO R B. Ras-ERK Signaling in Behavior: Old Questions and New Perspectives.[J]. Frontiers in Behavioral Neuroscience, 2011, 5: 79. DOI: 10.3389/fnbeh.2011.00079
Spectrum DetailBack Directory
[Spectrum Detail]

SL 327(305350-87-2)MS
SL 327(305350-87-2)1HNMR
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