256935-98-5

Basic information

• Product Name: Methyl 7-fluoro-1H-indole-5-carboxylate
• Synonyms: Methyl 7-fluoro-1H-indole-5-carboxylate;1H-INDOLE-5-CARBOXYLIC ACID, 7-FLUORO-, METHYL ESTER
• CAS NO: 256935-98-5
• Molecular Formula: C₁₀H₈FNO₂
• Molecular Weight: 193.1744232
• Mol File: 256935-98-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 343.7±27.0 °C(Predicted)
• Appearance: /
• Density: 1.341±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.63±0.30(Predicted)
• CAS DataBase Reference: Methyl 7-fluoro-1H-indole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 7-fluoro-1H-indole-5-carboxylate(256935-98-5)
• EPA Substance Registry System: Methyl 7-fluoro-1H-indole-5-carboxylate(256935-98-5)

Safety Data

• Hazardous Substances Data: 256935-98-5(Hazardous Substances Data)

Usage

Description

Methyl 7-fluoro-1H-indole-5-carboxylate is a chemical compound with the molecular formula C11H8FNO2. It is a fluoro-substituted derivative of indole, a heterocyclic compound commonly found in many natural products and pharmaceuticals. The presence of the fluoro group makes this compound useful in medicinal chemistry as it can influence the biological activity and properties of the molecule.

Uses

Used in Drug Development:
Methyl 7-fluoro-1H-indole-5-carboxylate is used as a building block for the synthesis of various pharmaceuticals and bioactive molecules. Its synthesis and properties are of interest to chemists and researchers working in the fields of organic and medicinal chemistry. The fluoro substitution can enhance the biological activity and properties of the resulting compounds, making them more effective for therapeutic applications.

Upstream product

• 256935-96-3 trifluoromethanesulfonic acid 7-fluoroindol-5-yl ester 
• 256935-94-1 trifluoromethanesulfonic acid 3-fluoro-4-nitrophenyl ester 
• 394-41-2 3-fluoro-4-nitrophenol 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 424834-58-2 5-hydroxymethyl-7-fluoroindole 
• 256935-99-6 7-fluoroindole-5-carboxylic acid 
• 424834-59-3 5-formyl-7-fluoroindole 

Relevant articles and documents

Potent, orally active heterocycle-based combretastatin A-4 analogues: Synthesis, structure - Activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation

The synthesis and structure - activity relationship study of a series of compounds with heterocycles in place of the cis double bond in combretastatin A-4 (CA-4) are described. Substituted tosylmethyl isocyanides were found to be the key intermediates in construction of the heterocycles. Cytotoxicities of the heterocycle-based CA-4 analogues were evaluated against NCI-H460 and HCT-15 cancer cell lines. 3-Amino-4-methoxyphenyl and N-methyl-indol-5-yl were the best replacements for the 3-hydroxy-4-methoxyphenyl in CA-4. 4,5-Disubstituted imidazole was found to be the best for the replacement of the cis double bond in CA-4. Medicinal chemistry efforts led to the discovery of compounds 24h and 25f that were found to be 32 and 82% bioavailable, respectively, in rat. Evaluation of 24h and 25f against murine M5076 reticulum sarcoma in mice revealed that both compounds were orally efficacious with an increase in life span of 38.5 and 40.5%, respectively.