132819-92-2

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-2-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, ethyl ester is used as a pharmaceutical intermediate for the development of new drugs. Its indole and sulfonyl groups are known to exhibit various biological activities, making it a promising candidate for drug discovery and design.
Used in Organic Synthesis:
In the field of organic synthesis, 1H-Indole-2-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, ethyl ester is used as a building block to create new chemical compounds with potential pharmacological properties. Its unique structure allows for the synthesis of a wide range of molecules with diverse therapeutic applications.

Upstream product

• 1189-60-2 propionic acid 3-methyl-but-2-enyl ester 
• 104699-53-8 ethyl 3-bromo-1-tosylindole-2-carboxylate 
• 3770-50-1 2-carbethoxyindole 
• 98-59-9 p-toluenesulfonyl chloride 
• 4755-77-5 Ethyl oxalyl chloride 
• 243844-35-1 N-[2-(chloromethyl)-phenyl]-4-methylbenzene-1-sulfonamide 
• 1477-50-5 Indole-2-carboxylic acid 
• 53398-80-4 propionic acid trans-2-hexen-1-yl ester 

Downstream Products

• 1323764-48-2 ethyl 3-[hydroxy(phenyl)methyl]-1-tosylindole-2-carboxylate 
• 104699-48-1 ethyl 3-allyl-1-tosylindole-2-carboxylate 
• 146384-54-5 1-(p-toluenesulfonyl)-1H-indole-2-carboxyaldehyde 
• 3770-50-1 2-carbethoxyindole 

Relevant academic research and scientific papers

Synthesis of the cyanobacterial metabolite nostodione A, structural studies and potent antiparasitic activity against Toxoplasma gondii

A total synthesis of the cyanobacterial natural product nostodione A is reported involving a convergent, diversity-oriented route, enabling the assembly of a mini-library of structural analogues. The first single crystal X-ray structural determination on a member of this series is reported along with SAR studies identifying potent inhibitors of invasion and replication of the parasitic protozoan Toxoplasma gondii.

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

1,5-Disubstituted indole-2-carboxaldehyde derivatives 1a–h and glycine alkyl esters 2a–c are shown to undergo a novel cascade imination-heterocylization in the presence of the organic base DIPEA to provide 1-indolyl-3,5,8-substituted γ-carbolines 3aa–ea in good yields. The γ-carbolines are fluorescent and exhibit anticancer activities against cervical, lung, breast, skin, and kidney cancer cells.

Tandem Phospha-Michael Addition/N-Acylation/ Intramolecular Wittig Reaction of aza-o-Quinone Methides: Approaches to 2,3-Disubstituted Indoles

A tandem phospha-Michael addition/N-acylation/intramolecular Wittig reaction of in situ formed aza-o-QMs is disclosed. This approach features high functional group tolerance and provides a convenient and practical access to biologically significant indole derivatives (37 examples, up to 91% yield) under mild reaction conditions. (Figure presented.).

Chromium-Catalyzed Asymmetric Dearomatization-Addition Reactions of Halomethyloxazoles and Indoles

The asymmetric dearomatization-addition reaction of halomethyloxazoles and halomethylindoles with aldehydes is realized in the presence of a carbazole-based bisoxazoline CrCl 2 complex to afford the corresponding enantioenriched, hydroxylated oxazoline and indoline products. The observed excellent chemo-, regio-, diastereo- and enantioselectivities are notable advantages of this protocol. The strategy established in this study is expected to find application in the synthesis of azaheterocycles with biological significance and useful functionalities.

Identification of indole scaffold-based dual inhibitors of NOD1 and NOD2

NOD1 and NOD2 are important members of the pattern recognition receptor family and play a crucial role within the context of innate immunity. However, overactivation of NODs, especially of NOD1, has also been implicated in a number of diseases. Surprisingly, NOD1 remains a virtually unexploited target in this respect. To gain additional insight into the structure–activity relationships of NOD1 inhibitors, a series of novel analogs has been designed and synthesized and then screened for their NOD1-inhibitory activity. Selected compounds were also investigated for their NOD2-inhibitory activity. Two compounds 4 and 15, were identified as potent mixed inhibitors of NOD1 and NOD2, displaying a balanced inhibitory activity on both targets in the low micromolar range. The results obtained have enabled a deeper understanding of the structural requirements for NOD1 and NOD2 inhibition.

Discovery of [5-Amino-1-(2-methyl-3H-benzimidazol-5-yl)pyrazol-4-yl]-(1H-indol-2-yl)methanone (CH5183284/Debio 1347), An Orally Available and Selective Fibroblast Growth Factor Receptor (FGFR) Inhibitor

The fibroblast growth factor receptor (FGFR) family of receptor tyrosine kinases regulates multiple biological processes, such as cell proliferation, migration, apoptosis, and differentiation. Various genetic alterations that drive activation of the recep

A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of N-Tosylaziridines Followed by Copper Powder-Mediated C-N Cyclization/Aromatization

A simple strategy for the syntheses of 2-alkyl indoles via regioselective ring-opening of 2-(2-haloaryl)-3-alkyl-N-tosylaziridines with thiophenol, followed by copper powder-mediated intramolecular C-N cyclization and subsequent aromatization by the elimi

INHIBITORS OF BRUTON'S TYROSINE KINASE

This application discloses compounds according to generic Formula (I): wherein all variables are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are useful for the treatment of oncological, auto-immune, and inflammatory diseases caused by aberrant B-cell activation. Also disclosed are compositions containing compounds of Formula I and at least one carrier, diluent or excipient.

Total synthesis of the cyanobacterial metabolite nostodione A: Discovery of its antiparasitic activity against Toxoplasma gondii

A total synthesis of the cyanobacterial natural product nostodione A is reported involving a convergent, diversity-oriented route. A small assemblage of structural analogues were prepared and their cytotoxicity and anti-invasion activity against the protozoal parasite Toxoplasma gondii is reported for the first time. This journal is the Partner Organisations 2014.