123892-57-9

Usage

Chemical Family

1H-Indole

Substituents

7-methyl, 1-[(4-methylphenyl)sulfonyl]

Molecular Structure

A bicyclic structure with a sulfonyl group attached to the 1-position and a 4-methylphenyl group further substituting the sulfonyl group.

Applications

Medicinal chemistry, pharmaceutical research, potential antitumor, antibacterial, and antifungal properties.

Usage

Chemical intermediate in organic synthesis, versatile building block for the preparation of various other organic compounds.

Upstream product

• 53848-17-2 2-bromo-6-methylaniline 
• 894810-85-6 N-p-toluenesulfonyl-2-bromo-6-methylaniline 
• 894810-46-9 N-allyl-4-methyl-N-(2-methyl-6-vinyl-phenyl)-benzenesulfonamide 
• 143262-04-8 N-tosyl-2-(1-isopropylthio-2-methoxyethyl)-6-methylanilide 
• 933-67-5 7-methyl-1H-indole 
• 98-59-9 p-toluenesulfonyl chloride 
• 95-53-4 o-toluidine 
• 143262-00-4 2-(1-isopropylthio-2-methoxyethyl)-6-methylaniline 
• 894810-86-7 N-p-toluenesulfonyl-2-ethenyl-6-methylaniline 

Downstream Products

• 1396259-60-1 C₃₅H₃₅NO₄ 
• 1396259-49-6 C₄₂H₄₁NO₆S 
• 887338-40-1 C₁₆H₁₄BrNO₂S 
• 1396260-29-9 1-(4-cyclopropylbenzyl)-7-methyl-3-(β-D-xylopyranosyl)-1H-indole 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors

Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors are the current focus on the indication for the management of hyperglycemia in diabetes. Here, a novel series of C-linked indolylxyloside-based inhibitors of SGLT2 has been discovered. Structure-activity relationship studies revealed that substituents at the 7-position of the indole moiety and a p-cyclopropylphenyl group in the distal position were necessary for optimum inhibitory activity. The pharmacokinetic study demonstrates that the most potent compound 1i is metabolically stable with a low clearance in rats. In further efficacy study, 1i is found to significantly lower blood glucose levels of streptozotocin (STZ)-induced diabetic rats.

Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles

A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.

SYNTHESIS OF 4-, 5-, 6- AND 7-SUBSTITUTED N-TOSYLINDOLES FROM SUBSTITUTED ANILINES

4-, 5-, 6-, and 7-Substituted N-tosylindoles are prepared from N-tosylanilides, carrying 2-acetoxy-1-(isopropylthio)ethyl group at the ortho position, which can be prepared from substituted anilines and dialkyl sulfide by sigmatropic rearrangement.