Meisoindigo

Base Information

• Chemical Name: Meisoindigo
• CAS No.: 97207-47-1
• Molecular Formula: C17H12N2O2
• Molecular Weight: 276.294
• Hs Code.: 2933990090
• UNII: 92UIP6405R
• DSSTox Substance ID: DTXSID901025868
• Nikkaji Number: J552.292G
• Wikidata: Q27271531
• ChEMBL ID: CHEMBL607535
• Mol file: 97207-47-1.mol

Synonyms:dian III;meisoindigo;N-methylisoindigotin

Chemical Property of Meisoindigo

Chemical Property:

• Vapor Pressure: 1.89E-09mmHg at 25°C
• Melting Point: 236-237°C
• Refractive Index: 1.698
• Boiling Point: 482 °C at 760 mmHg
• Flash Point: 245.3 °C
• PSA: 49.41000
• Density: 1.381 g/cm³
• LogP: 2.72890
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥25.85 mg/mL in DMSO with ultrasonic
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 276.089877630
• Heavy Atom Count: 21
• Complexity: 614

Purity/Quality:

99% ^*data from raw suppliers

Meisoindigo ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=C1O)C3=C4C=CC=CC4=NC3=O
• Description: Meisoindigo is a derivative of indirubin that has anticancer activity. It inhibits the growth of NB4, HL-60, and U937 leukemia and primary acute myeloid leukemia (AML) cells when used at concentrations of 5 and 10 μM. It also halts the cell cycle at the G0/G1 phase and induces apoptosis in leukemia cell lines and primary AML cells, induces myeloid differentiation, and potentiates the effects of cytarabine and idarubicin . Meisoindigo (10 μM) also induces apoptosis, decreases adherence, and decreases the expression of vascular cell adhesion molecule-1 (VCAM-1) in ECV304 human vein endothelial cells. Meisoindigo (50-150 mg/kg per day) decreases spleen size in an HL-60 mouse xenograft model of AML in a dose-dependent manner.
• Uses: Meisoindigo is a 5-HT3 receptor antagonist prevents acute nausea and vomiting associated with emetogenic cancer chemotherapy Meisoindigo shows strong anti-proliferation effect against gemcitabine-resistant Pancreatic ductal adenocarcinoma (PDACs).

Technology Process of Meisoindigo

There total 18 articles about Meisoindigo 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: 86.0%

2-oxoindole (59-48-3) + 1-methyl-1H-indole-2,3-dione (2058-74-4) → (E)-1-methyl-[3,3'-biindolinylidene]-2,2'-dione (97207-47-1)

Guidance literature:

With zirconium(IV) chloride; In ethanol; Reflux;

DOI:10.1016/j.tetlet.2016.11.053

Reference yield: 85.0%

(E)-1-(4-methoxybenzyl)-1'-methyl-[3,3'-biindolinylidene]-2,2'-dione → (E)-1-methyl-[3,3'-biindolinylidene]-2,2'-dione (97207-47-1)

Guidance literature:

With trifluorormethanesulfonic acid; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/adsc.201600767

Reference yield: 82.0%

3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one (58956-40-4) → methylisoindigotin (97207-47-1)

Guidance literature:

With trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; water; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Reflux;

DOI:10.1002/bkcs.11317

upstream raw materials:

2-oxoindole

1-methyl-1H-indole-2,3-dione

N-methyl-2-indolinone

indole-2,3-dione

Refernces

• 1、 Zhang, Hong-Hua,Wang, Yong-Qiang,Huang, Long-Tao,Zhu, Long-Qing,Feng, Yi-Yue,Lu, Ying-Mei,Zhao, Quan-Yi,Wang, Xue-Qiang,Wang, Zhen. "NaI-mediated divergent synthesis of isatins and isoindigoes: A new protocol enabled by an oxidation relay strategy". supporting information. p. 8265 - 8268. Retrieved 2018/07/29.
• 2、 Liu, Meilin,Qiu, Shaozhong,Ye, Yu,Yin, Guodong. "Mild and efficient synthesis of isoindigo derivatives catalyzed by Lewis acid". supporting information. p. 5856 - 5858. Retrieved 2016/12/07.