Bisindolylmaleimide v

Base Information

• Chemical Name: Bisindolylmaleimide v
• CAS No.: 113963-68-1
• Molecular Formula: C21H15N3O2
• Molecular Weight: 341.3627
• Hs Code.: 2933990090
• European Community (EC) Number: 601-289-1
• DSSTox Substance ID: DTXSID50150620
• Nikkaji Number: J442.994J
• Wikidata: Q72446081
• Metabolomics Workbench ID: 94441
• ChEMBL ID: CHEMBL291725
• Mol file: 113963-68-1.mol

Synonyms:2,3-bis(indol-3-yl)-N-methylmaleimide;bisindolylmaleimide V

Chemical Property of Bisindolylmaleimide v

Chemical Property:

• Appearance/Colour: Red solid.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >260 °C
• Refractive Index: 1.794
• Boiling Point: 655.691 °C at 760 mmHg
• PKA: 15.89±0.30(Predicted)
• Flash Point: 350.349 °C
• PSA: 68.96000
• Density: 1.451 g/cm³
• LogP: 3.49650
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 341.116426730
• Heavy Atom Count: 26
• Complexity: 604

Purity/Quality:

99% ^*data from raw suppliers

Bisindolylmaleimide V ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)C(=C(C1=O)C2=CNC3=CC=CC=C32)C4=CNC5=CC=CC=C54
• Description: Ro 31-6045 (113963-68-1) is a bis indolylmaleimide derivative that is a potent inhibitor of the mitogen-stimulated protein kinase p70 (S6K) acting independently of its upstream activator mTOR.1?Does not inhibit PKC (at concentrations <100?mM) and therefore may be used as a negative control for bisindolylmaleimide PKC inhibitors2?such as GF 109203X3?and other structurally related inhibitors4.

Technology Process of Bisindolylmaleimide v

There total 24 articles about Bisindolylmaleimide v which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

3,4-dichloro-1-methyl-pyrrole-2,5-dione (1123-61-1) + indolylmagnesium bromide → bisindolylmaleimide V (113963-68-1)

Guidance literature:

In toluene;

DOI:10.1016/j.bmcl.2005.04.015

Reference yield: 94.0%

3-(1H-indol-3-yl)-4-[1-{tert-butyloxycarbonyl}indol-3-yl]-1-methyl-1H-pyrrole-2,5-dione (119139-20-7) → bisindolylmaleimide V (113963-68-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 8h; Heating;

DOI:10.1016/S0040-4039(01)02225-0

Reference yield: 89.0%

3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione (119139-23-0) + methyl iodide (74-88-4) → bisindolylmaleimide V (113963-68-1)

Guidance literature:

3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione; With potassium hydroxide; In acetone; at 0 ℃; for 0.5h;

methyl iodide; In acetone; at 0 - 20 ℃;

DOI:10.1016/j.cclet.2017.08.019

upstream raw materials:

indole

3,4-dibromo-1-methyl-2,5-dihydropyrrole-2,5-dione

(Indol-1-yl)magnesium iodide

3,4-dichloro-1-methyl-pyrrole-2,5-dione

Downstream raw materials:

C₃₇H₃₇N₅O₅

C₃₂H₂₉N₅O₃

Ruboxistaurin mesylate

(9S)-6,7,10,11-tetrahydro-9-[(triphenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]-oxadiazacyclohexadecine-18,20(19H)-dione

Refernces

• 1、 Zhang, Qianfeng,Chang, Guanjun,Zhang, Lin. "Synthesis and properties of novel heat-resistant fluorescent conjugated polymers with bisindolylmaleimide". . p. 513 - 516. Retrieved 2018.
• 2、 Wang, Ke,Liu, Zhanzhu. "Synthesis of arcyriarubin a and arcyriaflavin a via cross-coupling of indolylboronic acid with dibromomaleimides". . p. 144 - 150. Retrieved 2010.
• 3、 Katoh, Miho,Dodo, Kosuke,Fujita, Mikako,Sodeoka, Mikiko. "Structure-activity relationship of N-methyl-bisindolylmaleimide derivatives as cell death inhibitors". . p. 3109 - 3113. Retrieved 2005.
• 4、 Zhang, Han-Cheng,White, Kimberly B.,Ye, Hong,McComsey, David F.,Derian, Claudia K.,Addo, Michael F.,Andrade-Gordon, Patricia,Eckardt, Annette J.,Conway, Bruce R.,Westover, Lori,Xu, Jun Z.,Look, Richard,Demarest, Keith T.,Emanuel, Stuart,Maryanoff, Bruce E.. "Macrocyclic bisindolylmaleimides as inhibitors of protein kinase C and glycogen synthase kinase-3". . p. 3049 - 3053. Retrieved 2003.
• 5、 -. "3. 4 - b (3 - indole) - 2, 5 - dione -3 - pyrroline imine compound and its preparation method and application". Paragraph 0048; 0049; 0053; 0054. . Retrieved 2017/07/25.