ChemicalBook > CAS DataBase List > 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione

3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione

Product Name: 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione
CAS No.: 119139-23-0
Chemical Name: 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione
Synonyms: RO 31-6233;ARCYRIARUBIN A;3,4-Di(1H-indol-3-yl);BISINDOLYMALEIMIDE IV;BISINDOLYLMALEIMIDE IV;Sotrastaurin Impurity 13;3,4-BIS(3-INDOLYL)MALEIMIDE;2,3-BIS(1H-INDOL-3-YL)MALEIMIDE;BisindolylMaleiMide IV [Ro 31-6233];Bisindolylmaleimide IV, PKC inhibitor
CBNumber: CB9354568
Molecular Formula: C20H13N3O2
Formula Weight: 327.34
MOL File: 119139-23-0.mol

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3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione Property

Melting point:: 161 °C
Boiling point:: 690.1±55.0 °C(Predicted)
Density: 1.486±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: DMSO: soluble
form: solid
pka: 8.44±0.60(Predicted)
color: dark red
biological source: synthetic (organic)

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Safety

WGK Germany: 3
HS Code: 2933.99.8290

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: B3306
Product name: Bisindolylmaleimide IV
Purity: ≥98% (TLC)
Packaging: 1mg
Price: $107
Updated: 2025/07/31

Sigma-Aldrich

Product number: 203297-M
Product name: Bisindolylmaleimide IV
Purity: A potent, cell permeable, and selective inhibitor of protein kinase C (IC₅₀ = 87 nM).
Packaging: 1 unit
Price: $207
Updated: 2025/07/31

TCI Chemical

Product number: B6068
Product name: Bisindolylmaleimide IV
Packaging: 50MG
Price: $129
Updated: 2025/07/31

TCI Chemical

Product number: B6068
Product name: Bisindolylmaleimide IV
Packaging: 250MG
Price: $445
Updated: 2025/07/31

Cayman Chemical

Product number: 13299
Product name: Bisindolylmaleimide IV
Purity: ≥98%
Packaging: 1mg
Price: $53
Updated: 2024/03/01

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3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione Chemical Properties,Usage,Production

Definition

ChEBI: 3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione is a member of indoles and a member of maleimides.

General Description

A potent, cell permeable, and selective inhibitor of protein kinase C (IC₅₀ = 87 nM). Inhibits protein kinase A at much higher concentrations (IC₅₀ = 2.7 μM).

Biological Activity

bisindolylmaleimide iv is a protein kinase c (pkc) inhibitor.the enzyme family protein kinase c2 (pkc) occupies a central role in the transduction of signals from a variety of mediators across the cell membrane.3 receptor occupation by a number of hormones, cytokines, neurotransmitters, and growth factors results in activation of pkc via activation of phospholipase c through either a g protein mechanism or a tyrosine kinase mechanism. pkc then propagates the signal by phosphorylation of proteins on serine or threonine, with atp as cosubstrate, resulting in modification of the properties of these proteins. thus pkc appears to regulate mechanisms of cell proliferation, secretion, and gene expression.

Biochem/physiol Actions

Target IC50: 87 nM against protein kinase C

Synthesis

879-37-8

18372-22-0

119139-23-0

A. Chemical Examples; Example 1; 3,4-Di-(1H-indol-3-yl)pyrrole-2,5-dione (Compound 1); Potassium tert-butanolate (0.976 g, 8.7 mmol) was added to a stirred (1H-indol-3-yl)acetamide (0.5 g, 2.8 mmol) and methyl 3-indolylglyoxylate (0.650 g, 3.15 mmol) in a suspension of anhydrous tetrahydrofuran (15 mL) and the temperature was maintained at -10 °C. After 15 minutes of reaction, the resulting dark red solution was slowly warmed to 20 °C over 3.5 hours. Subsequently, concentrated hydrochloric acid (2 mL) was added under cooling conditions and stirred overnight to dissolve the orange-red precipitate in ethyl acetate. The organic phase was washed sequentially with water and brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give bisindolylmaleimide IV (0.780 g, 80.2% yield) in red crystalline form with a melting point of 234 °C. 1H-NMR (DMSO-d6, δ/ ppm): 11.6 (br s, 1H), 10.95 (br s, 1H), 7.68 (s, 1H) , 7.38 (d, 1H), 6.98 (t, 1H), 6.8 (d, 1H), 6.6 (t, 1H).

in vitro

bisindolylmaleimide iv was identified as a cell permeable inhibitor of protein kinase c (pkc) with ic50 values from 0.10 to 0.55 μm. bisindolylmaleimide iv was designed to be more discriminative than its parent compound staurosporine, the non-selective pkc inhibitor. in addition, bisindolylmaleimide iv also found to be able to inhibit protein kinase a with ic50 values ranging from 2 to 11.8 μm [1, 2].

in vivo

animal study found that, in neonatal rats, high glucose levels could induce the hypertrophy of cardiomyocytes. ro-31-8220, a analog of bisindolylmaleimide viii, was able to reverse the effect of high glucose on the cardiac myocytes, which might be through pkc/nf-κb/c-fos pathway [3].

IC 50

from 0.10 to 0.55 μm

References

[1] davis, p. d.,hill, c.h.,lawton, g., et al. inhibitors of protein kinase c. 1.1 2,3-bisarylmaleimides. journal of medicinal chemistry 35, 177-184 (1992).
[2] toullec, d. ,pianetti, p.,coste, h., et al. the bisindolylmaleimide gf 109203x is a potent and selective inhibitor of protein kinase c. the journal of biological chemisty 266(24), 15771-15781 (1991).
[3] zhang, w. b. et al. reverse effect of protein kinase c inhibitor ro-31-8220 on the hypertrophy of cardiomyocytes of neonatal rats induced by high glucose levels. chinese journal of pathophysiology. 2009-08.

3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione Preparation Products And Raw materials

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View Lastest Price from 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione manufacturers

Career Henan Chemical Co

Product: 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione 119139-23-0
Price: US $9.80/KG
Min. Order: 1KG
Purity: ≥98%
Supply Ability: 20 tons
Release date: 2020-01-10

119139-23-0, 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dioneRelated Search:

D-ERYTHRO-SPHINGOSINE Bisindolylmaleimide V Maleimide GF109203X 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione RO-31-7549 GO 6983 RUBOXISTAURIN HYDROCHLORIDE RO-31-8425 BISINDOLYLMALEIMIDE III RO 31-8220 METHANESULFONATE 2-[1-(3-AMINOPROPYL)-1H-INDOL-3-YL]-3-(1H-INDOL-3-YL)MALEIMIDE, HCL BISINDOLYLMALEIMIDE VII RO-31-8220 3-(1H-indol-3-yl)-4-(5-methoxy-1H-indol-3-yl)-1H-pyrrole-2,5-dione 3,4-bis(5-methoxy-1H-indol-3-yl)-1H-pyrrole-2,5-dione rim 1 BISINDOLYLMALEIMIDE VI

RO 31-6233

3,4-BIS(3-INDOLYL)MALEIMIDE

2,3-BIS(1H-INDOL-3-YL)MALEIMIDE

Bisindolylmaleimide IV - CAS 119139-23-0 - Calbiochem

Bisindolylmaleimide IV (Arcyriarubin A)

3,4-BIS(3-INDOLYL)MALEIMIDE (ARCYRIARUBIN A), 95+%

3,4-BIS(3-INDOLYL)MALEIMIDE (ARCYRIARUBIN A).

3-(1H-Indole-3-yl)-4-(1H-indole-3-yl)-1H-pyrrole-2,5-dione

3,4-Bis(1H-indol-3-yl)-1H-pyrrole-2,5-dione

1H-Pyrrole-2,5-dione, 3,4-di-1H-indol-3-yl-

BisindolylMaleiMide IV [Ro 31-6233]

bisindolylmaleimide iv:2,3-bis(1h-indol-3-yl)maleimide: 3,4-di-1h-indol-3-yl-1h-pyrrole-2,5-dione

3,4-Bis(1H-indol-3-yl)pyrrole-2,5-dione

3,4-Di(1H-indol-3-yl)

BISINDOLYLMALEIMIDE IV

ARCYRIARUBIN A

BISINDOLYMALEIMIDE IV

3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione

3,4-Di(3-indolyl)-1H-pyrrole-2,5-dione

Sotrastaurin Impurity 13

Bisindolylmaleimide IV, PKC inhibitor

Bisindolylmaleimide IV, 10 mM in DMSO

119139-23-0

C20H13N3O2

Cell Signaling and Neuroscience

BioChemical

Cell Biology

Kinase/Phosphatase Biology

Protein Kinase C (PKC)

Serine/Threonine Kinase Inhibitors