Indirubin

Base Information

• Chemical Name: Indirubin
• CAS No.: 479-41-4
• Molecular Formula: C16H10N2O2
• Molecular Weight: 262.268
• Hs Code.: 29339900
• NSC Number: 105327
• UNII: 1LXW6D3W2Z,V86L8P74GI
• DSSTox Substance ID: DTXSID201026053,DTXSID501026052
• Nikkaji Number: J6.158A
• Wikipedia: Indirubin
• Wikidata: Q1661452,Q27164070,Q104968482,Q104389757
• Pharos Ligand ID: QDNW193D3UAZ
• ChEMBL ID: CHEMBL259664,CHEMBL35349,CHEMBL1276127,CHEMBL3185783
• Mol file: 479-41-4.mol

Synonyms:indigo red;indirubin

Chemical Property of Indirubin

Chemical Property:

• Appearance/Colour: Reddish-violet powder
• Vapor Pressure: 5.34E-10mmHg at 25°C
• Melting Point: 350°C(lit.)
• Refractive Index: 1.709
• Boiling Point: 496.6 °C at 760 mmHg
• PKA: 9.13±0.20(Predicted)
• Flash Point: 207 °C
• PSA: 58.20000
• Density: 1.417 g/cm³
• LogP: 2.93420
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 262.074227566
• Heavy Atom Count: 20
• Complexity: 448

Purity/Quality:

≥98% ^*data from raw suppliers

Indirubin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(N2)O)C3=NC4=CC=CC=C4C3=O
• Description: Indirubin is the active ingredient of Danggui Longhui Wan, a traditional Chinese medicine containing plants such as Indigofera tinctoria L. and Isatis tinctoria L, which are used in traditional Chinese medicine to treat chronic diseases. Indirubin and its analogues are reported as potent inhibitors of cyclin-dependent kinases (CDKs). This could attribute to the positive effect of indirubin on counteracting proliferative diseases, such as chronic myelocytic leukemia (CML), a slowly progressive disease characterized by the overproduction of granulocytes. A further alkaloid isolated from the matured fruit of Couroupita guianensis, this base forms red crystals from EtOH and melts above 340°C. It forms the Nacetyl derivative, m.p. 186°C. The full structure has not yet been established.
• Physical properties: Appearance: dark red acicular crystal with sublimate, odorless, and tasteless. Solubility: slightly soluble in dimethyl sulfoxide (DMSO) or tetrahydrofuran, very slightly soluble in chloroform or acetone, and insoluble in ethanol, ethyl ether, or water. Melting point: 348–353 °C. The stability of indirubin is poor that it needs to be stored away from light and thermal environment.
• Uses: Indigopurpurin is a purple 3,2-bisindole derivative and was shown to exhibit inhibitory allergic contact dermatitis via regulating T helper (Th)-mediated immune system in DNCB-induced model. An inhibitor of GSK-3β and cyclin-dependent kinases. Indigopurpurin is a purple 3,2-bisindole derivative and was shown to exhibit inhibitory allergic contact dermatitis via regulating T helper (Th)-mediated immune system in DNCB-induced model. A possible glycogen synthase kinase-3 (GSK-3) inhibitor the active component of a traditional Congolese antiepilepsy treatment.
• Indications: Indirubin is contained in the fourth volume of the book, “National standards for chemical drugs.” Indirubin tablets are used for the therapy of chronic myelocytic leukemia in clinical.
• Clinical Use: Indirubin is mainly used for chronic myeloid leukemia; its total effective rate was 87.3%. The effect of indirubin to decrease white blood cells is similar to Maryland. The effect of indirubin to reduce liver is better than that of Maryland. But the remission role of the blood and bone marrow is worse than Maryland, and no cross resistance with Maryland. Indirubin could be used for abnormal bone marrow hyperplasia and eosinophilia.

Technology Process of Indirubin

There total 88 articles about Indirubin 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: 85.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → indirubin (479-41-4) + indirubin (479-41-4)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; In methanol; at 25 ℃; for 12h;

DOI:10.1016/S0031-9422(01)00335-1

Reference yield: 85.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → indirubin (479-41-4) + indirubin (479-41-4)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; In methanol; at 25 ℃; for 12h;

DOI:10.1016/S0031-9422(01)00335-1

Reference yield: 75.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → indirubin (479-41-4) + 1,2-bis(diphenylphosphinoyl)ethane (4141-50-8)

Guidance literature:

In tetrahydrofuran; for 2h; Reflux;

DOI:10.3184/174751916X14655742365588

upstream raw materials:

2-oxoindole

2-chloro-3H-indol-3-one

benzene

(E)-1H-indole-2,3-dione 3-oxime

Downstream raw materials:

(Z)-1'-benzoyl-1H,1'H-[2,3']biindolylidene-3,2'-dione

indirubin-3'-monoxime

indirubin-3'-monoxime

indole-2,3-dione

Refernces

Novel synthesis of 4-or 6-substituted indirubin derivatives

10.1080/00397910903318591

Indirubin derivatives are known for their high activity against various experimental solid tumors and their ability to inhibit cyclin-dependent kinases (CDKs) and glycogen synthase kinases-3 (GSK-3), which play important roles in diseases like cancers. The study explores a simple and convenient route involving oxidation and subsequent condensation of indoxyl and isatin. Acidic reaction conditions are crucial for the condensation of 4-substituted derivatives due to steric hindrance, while both acidic and basic conditions work well for 6-substituted derivatives. The authors successfully synthesized a range of 4- and 6-substituted indirubin derivatives and confirmed their structures using various spectroscopic techniques. The findings provide a novel approach to synthesizing these potentially therapeutic compounds, which could have significant implications for cancer treatment and other related diseases.