3-amino-3-[(4-aminophenyl)sulfanyl]-2-[2-(trifluoromethyl)phenyl]prop-2-enenitrile

• ChemBase ID: 154982
• Molecular Formular: C16H12F3N3S
• Molecular Mass: 335.3467896
• Monoisotopic Mass: 335.07040306
• SMILES: c1ccc(c(c1)/C(=C(\N)/Sc1ccc(cc1)N)/C#N)C(F)(F)F
• Canonical SMILES: N#C/C(=C(\Sc1ccc(cc1)N)/N)/c1ccccc1C(F)(F)F
• InChI: 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
• InChIKey: JLOXTZFYJNCPIS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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
• IUPAC Traditional name: 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
• Synonyms: α-[Amino-(4-aminophenylthio)methylene)-2-(trifluoromethyl)phenylacetonitrile; SL327; SL327

Database IDs

• CAS Number: 305350-87-2
• MDL Number: MFCD06411432
• PubChem SID: 162249120
• PubChem CID: 9549284

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.7926073
• LogD (pH = 7.4): 3.80333
• Log P: 3.8034685
• Molar Refractivity: 97.0138 cm^3
• Polarizability: 31.439531 Å^3
• Polar Surface Area: 75.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: white to off-white solid
• Melting Point: 127-128.2 °C

Safety Information

• Storage Condition: desiccated; protect from light
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: MEK

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C16H12F3N3S

DETAILS

Sigma Aldrich - S4069

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.