97207-47-1

Basic information

• Product Name: Meisoindigo
• Synonyms: 1-METHYL-3,3'-BIINDOLE-2,2'(1H,1'H)-DIONE;3-(1,2-dihydro-2-oxo-3h-indol-3-ylidene)-1,3-dihydro-1-methyl-2h-indol-2-one;MEISOINDIGO;N-methylisoindigotin;Dian III;Methylisoindigotin;Natura-α;Meisoindigo 3-(1,2-Dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-1-methyl-2H-indol-2-one
• CAS NO: 97207-47-1
• Molecular Formula: C₁₇H₁₂N₂O₂
• Molecular Weight: 276.29
• EINECS: 200-256-5
• Product Categories: Inhibitors
• Mol File: 97207-47-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 236-237°C
• Boiling Point: 482 °C at 760 mmHg
• Flash Point: 245.3 °C
• Appearance: /
• Density: 1.381 g/cm³
• Vapor Pressure: 1.89E-09mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: insoluble in H2O; insoluble in EtOH; ≥25.85 mg/mL in DMSO with ultrasonic
• CAS DataBase Reference: Meisoindigo(CAS DataBase Reference)
• NIST Chemistry Reference: Meisoindigo(97207-47-1)
• EPA Substance Registry System: Meisoindigo(97207-47-1)

Safety Data

• Hazardous Substances Data: 97207-47-1(Hazardous Substances Data)

Usage

Description

Meisoindigo is a derivative of indirubin that possesses anticancer activity. It inhibits the growth of various leukemia cells and demonstrates potent anti-proliferation effects against gemcitabine-resistant pancreatic ductal adenocarcinoma (PDACs). Meisoindigo also acts as a 5-HT3 receptor antagonist, which helps prevent acute nausea and vomiting associated with emetogenic cancer chemotherapy.

Uses

Used in Oncology:
Meisoindigo is used as an anticancer agent for the treatment of pancreatic ductal adenocarcinoma (PDACs), particularly in cases that are resistant to gemcitabine. It is effective in inhibiting the growth of cancer cells and has the potential to be a promising therapeutic candidate for PDAC treatment.
Used in Leukemia Treatment:
Meisoindigo is used as a treatment for leukemia, specifically for NB4, HL-60, and U937 leukemia cells, as well as primary acute myeloid leukemia (AML) cells. It halts the cell cycle at the G0/G1 phase, induces apoptosis, and promotes myeloid differentiation. Additionally, Meisoindigo potentiates the effects of cytarabine and idarubicin, enhancing the overall efficacy of leukemia treatment.
Used in Cancer-related Nausea and Vomiting Management:
Meisoindigo is used as a 5-HT3 receptor antagonist to prevent acute nausea and vomiting associated with emetogenic cancer chemotherapy. This application helps improve the quality of life for cancer patients undergoing chemotherapy by reducing the severity of these side effects.
Used in Angiogenesis Inhibition:
Meisoindigo (10 μM) is used to induce apoptosis, decrease adherence, and reduce the expression of vascular cell adhesion molecule-1 (VCAM-1) in ECV304 human vein endothelial cells. This suggests that Meisoindigo may have potential applications in inhibiting angiogenesis, a process crucial for tumor growth and metastasis.
Used in AML Mouse Xenograft Model:
In an HL-60 mouse xenograft model of AML, Meisoindigo (50-150 mg/kg per day) is used to decrease spleen size in a dose-dependent manner. This indicates that Meisoindigo may have potential applications in treating AML and reducing the associated symptoms in preclinical models.

references

[1] lee cc, lin cp, lee yl, wang gc, cheng yc, liu he. meisoindigo is a promising agent with in vitro and in vivo activity against human acute myeloid leukemia. leuk lymphoma. 2010 may;51(5):897-905.

InChI:InChI=1/C17H12N2O2/c1-19-13-9-5-3-7-11(13)15(17(19)21)14-10-6-2-4-8-12(10)18-16(14)20/h2-9H,1H3,(H,18,20)/b15-14+

Upstream product

• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 120-72-9 indole 
• 75833-71-5 1'-methyl-1H,1''H-[3,3':3',3''-terbenzo[b]pyrrol]-2'(1'H)-one 
• 58956-40-4 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one 
• 59-48-3 2-oxoindole 
• 61-70-1 N-methyl-2-indolinone 
• 3526-43-0 N-(4-methoxybenzyl)aniline 
• 100-61-8 N-methylaniline 
• 91-56-5 indole-2,3-dione 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 62-53-3 aniline 
• 16990-73-1 2-Hydroxyindole 

Relevant articles and documents

POLYMORPHIC FORM OF MEISOINDIGO AND MODIFIED FORMULATION OF MEISOINDIGO

The present invention relates to a novel crystal form, manufacturing procedures, pharmaceutical compositions, formulations and medicaments comprising a N-methylisoindigo crystalline, methods of preparation, and the use of the N-methylisoindigo crystalline to prepare a medicament to prevent cancer, or treat cancer or an inflammatory-related disease associated with pro-inflammatory cytokine expression and/or reduced expression of anti-inflammatory cytokines.

Facile Synthesis of Isoindigo Derivatives from 3-Indolyl-2-Oxindoles with DDQ

-

Mild and efficient synthesis of isoindigo derivatives catalyzed by Lewis acid

A mild and efficient ZrCl4-catalyzed synthesis of isoindigo derivatives from isatins and indolin-2-ones in refluxing ethanol is described. A variety of new functionalized isoindigo derivatives are obtained by simple filtration. Lewis acid was f