3285-40-3

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl 5-Methoxy-2-Methylindole-3-acetate is used as a synthetic intermediate for the development of indomethacin analogues, which are nonsteroidal anti-inflammatory agents. These analogues are designed to inhibit P-glycoprotein and/or MDR protein without COX-1/COX-2 inhibitory activity, making them potentially more effective and safer alternatives to traditional NSAIDs.
Additionally, Benzyl 5-Methoxy-2-Methylindole-3-acetate is used in the synthesis of indole-based prostaglandin D receptor antagonists. These antagonists have potential applications in the treatment of various conditions, such as allergic diseases, inflammatory disorders, and neurological disorders, by modulating the activity of the prostaglandin D receptor.

Upstream product

• 7588-36-5 methyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate 
• 1076-74-0 5-methoxy-2-methyl-1H-indole 
• 81867-37-0 benzyl iodoacetate 
• 2882-15-7 5-Methoxy-2-methylindole-3-acetic acid 
• 501-53-1 benzyl chloroformate 
• 100-51-6 benzyl alcohol 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 

Downstream Products

• 26001-79-6 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid benzyl ester 
• 1254180-95-4 [1-(2-chloropyridine-4-carbonyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid benzyl ester 
• 1321938-57-1 benzyl [5-methoxy-2-methyl-1-(4-{[(2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl]methoxy}benzoyl)-1H-indol-3-yl]acetate 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 343859-14-3 1-(1-adamantoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid benzyl ester 

Relevant academic research and scientific papers

Ortho-Carbaborane derivatives of indomethacin as cyclooxygenase (COX)-2 selective inhibitors

A series of novel indomethacin analogues with carbaboranes as three-dimensional substitutes for the chlorophenyl ring have been prepared. Their cyclooxygenase (COX) inhibition and enzyme selectivity has been tested and compared to the corresponding adamantyl analogues. Surprisingly, only the ortho-carbaborane derivatives were active compounds. Preliminary biological studies gave an interesting insight into the validity of employing carbaboranes as pharmacophores.

Synthesis and biological evaluation of indomethacin analogs possessing a N-difluoromethyl-1,2-dihydropyrid-2-one ring system: A search for novel cyclooxygenase and lipoxygenase inhibitors

A novel class of indomethacin analogs were synthesized wherein a N-difluoromethyl-1,2-dihydropyrid-2-one moiety (5-LOX pharmacophore) was attached at its C-4 or C-5 position via either a CO (14a-b) or CH2 (19a-b) linker to the indole N1-position. In this regard, replacement of the 4-chlorobenzoyl group present in indomethacin by N-difluoromethyl-1,2- dihydropyrid-2-one-4-(or 5-)carbonyl and N-difluoromethyl-1,2-dihydropyrid-2- one-4-yl(or 5-yl)methylene moieties furnished compounds showing no inhibitory activities against the COX-2/5-LOX enzymes (except for the weak but selective COX-2 inhibitor 19a, COX-2 IC50 = 31 μM), and moderate in vivo anti-inflammatory activities (except for the methylene compound 19a that was inactive). These structure-activity data indicate replacement of the 4-chlorobenzoyl group present in indomethacin by a N-difluoromethyl-1,2- dihydropyrid-2-one ring system connected by a CO or CH2 linker is not a suitable approach for the design of dual COX-2/5-LOX inhibitory analogs of indomethacin.

Aromatic enamide/ene metathesis toward substituted indoles and its application to the synthesis of indomethacins

A. steric and electronic effect: on enamide/ene metathesis, a novel preparation of 2-substituted indoles and 3-substituted indoles using enamide-ene metathesis as a key reaction, and its application to the synthesis of indoniethacin are described. Wiley-VCH Verlag GmbH & Co. KGaA.

Esters and amides of substituted pyrrole acetic acids

Esters and amides of substituted pyrrole acetic acids are useful in the treatment of colonic polyps.