10242-01-0

Basic information

• Product Name: 5-Methoxy-3-indolecarboxylic acid
• Synonyms: 5-METHOXY-3-CARBOXYINDOLE;5-METHOXY-3-INDOLECARBOXYLIC ACID;5-METHOXYINDOLE-3-CARBOXYLIC ACID;5-METHOXY-1H-INDOLE-3-CARBOXYLIC ACID;RARECHEM AL BE 0096;5-Methoxyindole-3-carboxylic Acid Hydrate;5-Methoxy-1H-indol-3-carboxylic acid;1H-Indole-3-carboxylic acid, 5-methoxy-
• CAS NO: 10242-01-0
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.18
• EINECS: 224-487-6
• Product Categories: Indoline & Oxindole
• Mol File: 10242-01-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 172-175 °C
• Boiling Point: 447.6 °C at 760 mmHg
• Flash Point: 224.5 °C
• Appearance: Red/Crystalline
• Density: 1.381 g/cm³
• Vapor Pressure: 8.54E-09mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.95±0.30(Predicted)
• CAS DataBase Reference: 5-Methoxy-3-indolecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-3-indolecarboxylic acid(10242-01-0)
• EPA Substance Registry System: 5-Methoxy-3-indolecarboxylic acid(10242-01-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 10242-01-0(Hazardous Substances Data)

Usage

Uses

5-Methoxyindole-3-carboxylic Acid can be used in the synthesis of benzoheterocycle derivatives as vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors and in the synthesis of indoleamine 2,3-dioxygenase 1 inhibitors with potential antitumor activity.

InChI:InChI=1/C10H9NO3/c1-14-6-2-3-9-7(4-6)8(5-11-9)10(12)13/h2-5,11H,1H3,(H,12,13)

Upstream product

• 1006-94-6 5-methoxylindole 
• 407-25-0 trifluoroacetic anhydride 
• 172595-68-5 methyl 5-methoxy-1H-indole-3-carboxylate 
• 124-38-9 carbon dioxide 
• 1051967-68-0 2,2,2-trifluoro-1-(5-methoxy-1H-indol-3-yl)ethan- 1- one 

Downstream Products

• 172595-68-5 methyl 5-methoxy-1H-indole-3-carboxylate 
• 1006-94-6 5-methoxylindole 
• 120-72-9 indole 
• 5883-83-0 5-methoxy-2-(4-methoxyphenyl)-1H-indole 
• 1404536-52-2 [4-(4-butyryl-5-methyl-pyrazol-1-yl)phenyl]-5-methoxy-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1H-indole-3-carboxamide hydrochloride 
• 1404532-97-3 sodium {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-methoxy-indol-1-yl}acetate 
• 1404532-65-5 {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-methoxy-indol-1-yl}acetic acid methyl ester 

Relevant articles and documents

Design, synthesis, and antitumor activity of novel benzoheterocycle derivatives as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase

The vascular endothelial growth factor receptor-2 signaling pathway promotes the formation of new blood vessels, and vascular endothelial growth factor receptor-2 tyrosine kinase exists in both active and inactive conformations. Novel indole–benzimidazole and indole–benzothiazole derivatives joined by different linkers are designed and synthesized as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase. All the synthesized compounds were evaluated for their cytotoxicity against four human cancer cell lines (HeLa, HT29, A549, and MDA-MB-435) and human umbilical vein endothelial cell. Meanwhile, the inhibitory activities against vascular endothelial growth factor receptor-2 are estimated in vitro and the binding interactions with dual conformations of vascular endothelial growth factor receptor-2 tyrosine kinase are evaluated by molecular docking. Compounds 5a–c and 14 show inhibitory activity against vascular endothelial growth factor receptor-2 tyrosine kinase and promising cytotoxicity, specifically with IC50 values ranging between 0.1 and 1 μM, which imply broad-spectrum antitumor activity. These results provide a deep insight into potential structural modifications for developing potent vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors.

METHODS OF TREATING CANCER

The present disclosure relates to methods of treating cancer in a patient using a combination of an inhibitor of an immune checkpoint protein and an indole compound or its phosphate derivative.

INDOLE COMPOUNDS AND THEIR USE

The present disclosure relates to indole compounds and pharmaceutical compositions thereof, and their use in stimulating the immune system of patients in need thereof and in treating cancer.