192189-13-2

Basic information

• Product Name: 1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-diMethylethyl ester
• Synonyms: 1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-diMethylethyl ester;tert-Butyl 5-fluoro-3-iodo-1H-indole-1-carboxylate;5-Fluoro-3-iodo-indole-1-carboxylic acid tert-butyl ester
• CAS NO: 192189-13-2
• Molecular Formula: C₁₃H₁₃FINO₂
• Molecular Weight: 361.1506932
• Mol File: 192189-13-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-diMethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-diMethylethyl ester(192189-13-2)
• EPA Substance Registry System: 1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-diMethylethyl ester(192189-13-2)

Safety Data

• Hazardous Substances Data: 192189-13-2(Hazardous Substances Data)

Usage

General Description

1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-dimethylethyl ester is a chemical compound with the molecular formula C15H15FINO2. It is a derivative of indole carboxylic acid and is commonly used in medicinal chemistry as a building block for the synthesis of various pharmaceutical drugs. The 5-fluoro-3-iodo substitution pattern on the indole ring makes this compound a valuable precursor for the development of new drug candidates with potential biological activity. Furthermore, the 1,1-dimethylethyl ester functional group enhances the compound's stability and solubility, making it easier to handle in laboratory settings. Overall, this chemical is of interest to researchers and pharmaceutical companies for its potential applications in drug discovery and development.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 868694-21-7 5-fluoro-3-iodo-1H-indole 
• 399-52-0 5-fluoro-1H-indole 

Downstream Products

• 1378477-76-9 C₃₀H₃₁FN₂O₅S 
• 1378478-02-4 C₃₀H₃₃FN₂O₆S 
• 2095464-28-9 tert-butyl 5-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate 

Relevant articles and documents

INDOLE DERIVATIVES AND USES THEREOF FOR TREATING A CANCER

The present invention relates to indole derivatives of formula (I') as CK2 inhibitor and pharmaceutical compositions comprising the same. The present invention further relates to the use of such compounds of formula (I) for use for preventing and/or treating a cancer.

Discovery of potent and specific dihydroisoxazole inhibitors of human transglutaminase 2

Transglutaminase 2 (TG2) is a ubiquitously expressed enzyme that catalyzes the posttranslational modification of glutamine residues on protein or peptide substrates. A growing body of literature has implicated aberrantly regulated activity of TG2 in the pathogenesis of various human inflammatory, fibrotic, and other diseases. Taken together with the fact that TG2 knockout mice are developmentally and reproductively normal, there is growing interest in the potential use of TG2 inhibitors in the treatment of these conditions. Targeted-covalent inhibitors based on the weakly electrophilic 3-bromo-4,5-dihydroisoxazole (DHI) scaffold have been widely used to study TG2 biology and are well tolerated in vivo, but these compounds have only modest potency, and their selectivity toward other transglutaminase homologues is largely unknown. In the present work, we first profiled the selectivity of existing inhibitors against the most pertinent TG isoforms (TG1, TG3, and FXIIIa). Significant cross-reactivity of these small molecules with TG1 was observed. Structure-activity and -selectivity analyses led to the identification of modifications that improved potency and isoform selectivity. Preliminary pharmacokinetic analysis of the most promising analogues was also undertaken. Our new data provides a clear basis for the rational selection of dihydroisoxazole inhibitors as tools for in vivo biological investigation.

An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations

An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives.