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

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

Uses

Used in Pharmaceutical Drug Synthesis:
1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-dimethylethyl ester is utilized as a key building block in the pharmaceutical industry for the development of new drug candidates. Its 5-fluoro-3-iodo substitution pattern on the indole ring endows the compound with valuable properties for biological activity, making it a promising precursor in the synthesis of drugs with potential therapeutic applications.
Used in Drug Discovery and Development:
In the field of drug discovery and development, 1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-dimethylethyl ester serves as a versatile chemical intermediate. Its unique structural features, including the 1,1-dimethylethyl ester group, enhance the compound's stability and solubility, facilitating its use in laboratory research and development processes. Researchers and pharmaceutical companies are interested in 1H-Indole-1-carboxylic acid, 5-fluoro-3-iodo-, 1,1-dimethylethyl ester for its potential to contribute to the creation of innovative and effective medications.

Upstream product

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

COMPOUNDS AND METHOD OF USE

This present disclosure relates to compounds with ferroptosis inducing activity, a method of treating a subject with cancer with the compounds, and combination treatments with a second therapeutic agent.

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.

One-pot synthesis of camalexins and 3,3′-biindoles by the Masuda borylation-Suzuki arylation (MBSA) sequence

The Masuda borylation/Suzuki arylation (MBSA) sequence starting from N-protected 3-iodoindoles has successfully been extended to the coupling of five-membered heterocycles and indoles in the arylation step, which could not be achieved with previously developed MBSA methods. By this approach the one-pot nature of the method as well as the use of a simple catalyst system has been retained. The applicability of the method has been demonstrated by the facile synthesis of camalexins and 3,3′-biindoles, compounds of special interest due to their pronounced antifungal, antimicrobial and cytotoxic activities. The Masuda borylation/Suzuki arylation sequence furnishes in a concise one-pot manner camalexins and 3,3′-biindoles, compounds that show pronounced antifungal, antimicrobial, and cytotoxic activities. Copyright

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.

One-pot synthesis of diazine-bridged bisindoles and concise synthesis of the marine alkaloid hyrtinadine A

Diazine-bridged bisindoles are readily obtained from N-Bocprotected 3-iodoindoles and 3-iodo-7-azaindole in a pseudo three-component reaction involving a one-pot Masuda borylation-Suzuki arylation sequence. Some of the title com-pounds display promising c

Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 6. 2-Indol-3-yl- and 2-azaindol-3-yl- dipyridodiazepinones

Modification of the non-nucleoside inhibitor of HIV-1 reverse transcriptase nevirapine (Viramune) by incorporation of a 2-indolyl substituent confers activity against several mutant forms of the enzyme.