U0126

Iupac Name：(2Z,3Z)-2,3-bis[amino-(2-aminophenyl)sulfanylmethylidene]butanedinitrile

Molecular Weight：380.49000

Modify Date.: 2022-11-02 18:03

Introduction: A chemically synthesized and highly selective inhibitor of both MEK1 and MEK2 with IC50s of 70 nM and 60 nM, respectively. View more+

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1. Names and Identifiers

1.1 Name: U0126
1.2 Synonyms: (2Z,3Z)-2,3-bis[amino-(2-aminophenyl)sulfanylmethylidene]butanedinitrile (2Z,3Z)-Bis{amino[(2-aminophenyl)sulfanyl]methylene}succinonitrile (2Z,3Z)-bis{amino[(2-aminophenyl)sulfanyl]methylidene}butanedinitrile 1,4-DIAMINO-2,3-DICYANO-1 1,4-DIAMINO-2,3-DICYANO-1,4-BIS(2-AMINOPHENYLTHIO)BUTADIENE 1,4-DIAMINO-2,3-DICYANO-1,4-BIS(2-AMINOPHYNYLTIO)BUTADIENE 1,4-DIAMINO-2,3-DICYANO-1,4-BIS(O-AMINOPHENYLMERCAPTO)BUTADIENE 2,3-Bis[amino[(2-aminophenyl)thio]methylene]butanedinitrile Butanedinitrile, 2,3-bis[amino[(2-aminophenyl)thio]methylene]-, (2Z,3Z)- U 0126 U-0126 UO 126

1.3 CAS No.: 109511-58-2

1.4 CID: 3006531

1.5 Molecular Formula: C18H16N6S2 (isomer)

1.6 Inchi: InChI=1S/C18H16N6S2/c19-9-11(17(23)25-15-7-3-1-5-13(15)21)12(10-20)18(24)26-16-8-4-2-6-14(16)22/h1-8H,21-24H2/b17-11+,18-12+

1.7 InChkey: DVEXZJFMOKTQEZ-JYFOCSDGSA-N

1.8 Canonical Smiles: C1=CC=C(C(=C1)N)SC(=C(C#N)C(=C(N)SC2=CC=CC=C2N)C#N)N

1.9 Isomers Smiles: C1=CC=C(C(=C1)N)S/C(=C(/C(=C(/SC2=CC=CC=C2N)\N)/C#N)\C#N)/N

2. Properties

2.1 Density: 1.44 g/cm3

2.1 Melting point: approximate 154℃(dec.)

2.1 Boiling point: 565.1ºC at 760 mmHg

2.1 Refractive index: 1.762

2.1 Flash Point: 295.6ºC

2.1 Precise Quality: 380.08800

2.1 PSA: 202.26000

2.1 logP: 5.68616

2.1 Appearance: White solid

2.2 Storage: Store at -20°C.

2.3 pKa: 2.11±0.10(Predicted)

2.4 Water Solubility: Soluble in DMSO

2.5 StorageTemp: Desiccate at +4°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A dinitrile that is succinonitrile in which the methylene hydrogens at positions 2 and 3 are substituted by (2-aminophenyl)sulfanyl]methylidene groups. A potent and selective non-competitive inhibitor of MAP kinase kinase.

3.2 Usage: A chemically synthesized and highly selective inhibitor of both MEK1 and MEK2 with IC50s of 70 nM and 60 nM, respectively.

4. Safety and Handling

4.1 RTECS: EJ9710000

5. Synthesis Route

109511-58-2Total: 1 Synthesis Route

14778-29-1 3 Suppliers

137-07-5 108 Suppliers

109511-58-2 24 Suppliers

Literatures:
US2779780 , ;
Yield: null

6. Precursor and Product

precursor:

137-07-5

14778-29-1

7. Other Information

7.0 Usage: U0126, is used as a selective MAP Kinase Kinase (MKK, MEK) inhibitor. U-0126 has been observed to inhibit promoters containing an AP-1 response element, while in contrast having no effect on promoters that lack an AP-1 response group. U-0126 is also useful in neuronal studies in mice since it displays inhibitory effects against oxidative stress. U-0126 is an activator of PGC-1, mtTFA and nuclear respiratory factor.

7.1 Uses: A chemically synthesized and highly selective inhibitor of both MEK1 and MEK2 with IC50s of 70 nM and 60 nM, respectively.

7.2 Definition: ChEBI: A dinitrile that is succinonitrile in which the methylene hydrogens at positions 2 and 3 are substituted by (2-aminophenyl)sulfanyl]methylidene groups. A potent and selective non-competitive inhibitor of MAP kinase kinase.

7.3 Biological Activity: Potent and selective non-competitive inhibitor of MAP kinase kinase. Inhibits MEK-1 and MEK-2 (IC 50 values of 0.07 and 0.06 μ M respectively) with little or no effect on the activities of PKC, Abl, Raf, MEKK, ERK, JNK, MKK-3, MKK-4/SEK, MKK-6, Cdk2 or Cdk4. Centrally active following systemic administration in vivo . Also available as part of the MAPK Cascade Inhibitor Tocriset? and MAPK Inhibitor Tocriset? .

7.4 MEK2 60 nM (IC 50 )

MEK1

70 nM (IC ₅₀ )

7.5 Cell Line:: A549 and MDCK II cells.

7.6 Concentration:: 0.001-1000 μM.

7.7 Incubation Time:: 48 h.

7.8 Result:: The EC ₅₀ values for U0126 against H1N1v were 1.2 ± 0.4 μM in A549 cells and 74.7 ± 1.0 μM in MDCKII cells

7.9 Animal Model:: Athymic female nude mice (SWISS, nu/nu).

7.10 Dosage:: 10.5 mg/kg.

7.11 Administration:: Intraperitoneal injection daily.

7.12 Result:: Inhibited tumor growth.

7.13 Animal Model:: Twelve-week-old female Wistar rats (250 to 265 g) .

7.14 Dosage:: 30 mg/kg.

7.15 Administration:: Intraperitoneally.

7.16 Result:: The vasoconstriction to S6c is markedly reduced.

7.17 Description: U-0126 is a MEK inhibitor with IC₅₀ values of 72 nM and 58 nM for MEK1 and MEK2, respectively. It is noncompetitive with respect adenosine triphosphate (ATP) and its phosphorylation target ERK and it shows little to no inhibition against a number of other kinases including PKC, Ab1, Raf, MEKK, ERK, JNK, MKK-3, MKK-4, MKK-6, Cdk2, and Cdk4. However, U-0126 does phosphorylate and activate AMP-activated protein kinase (AMPK) in a dose-dependent manner (EC₅₀ = 15 μM in HEK293 cells). It increases the ratios of ADP to ATP and AMP to ATP and increases phosphorylation of the AMPK target acetyl-CoA carboxylase (ACC).

7.18 Uses: U0126 is a MEK inhibitor.

7.19 General Description: A potent and specific inhibitor of MEK1 (IC₅₀ = 72 nM) and MEK2 (IC₅₀ = 58 nM). The inhibition is noncompetitive with respect to MEK substrates, ATP and ERK. Has very little effect on other kinases, such as Abl, Cdk2, Cdk4, ERK, JNK, MEKK, MKK-3, MKK-4/SEK, MKK-6, PKC, and Raf. Shown to block doxazosin-induced osteoblastic differentiation. U0126 also acts as an immunosuppressant by effectively blocking IL-2 synthesis and T cell proliferation without affecting the long-term outcomes of either T cell activation or tolerance. Noncompetitive with respect to ATP. Also available in InSolution format (Cat. No. 662009.

8. Computational chemical data

Molecular Weight: 380.49000g/mol
Molecular Formula: C₁₈H₁₆N₆S₂
Compound Is Canonicalized: True
XLogP3-AA: 2
Exact Mass: 380.08778688
Monoisotopic Mass: 380.08778688
Complexity: 610
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 8
Topological Polar Surface Area: 202
Heavy Atom Count: 26
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 2
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB7gABgAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHAQQAAAADAiBUAAwwYBAAAiQBiRCQACiAABgChAIiBwAZIgIoCKgkZGAIABgkAAIyA8QAAAAAAAAAAAAAQAAAAAAAAACAAAAAAAAAA==

9. Recommended Suppliers

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1,4-DIAMINO-2,3-DICYANO-1,4-BIS(2-AMINOPHENYLTHIO)BUTADIENE 109511-58-2 supplier

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2019/02/25

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U0126