26001-79-6

Basic information

• Product Name: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, phenylmethyl ester
• Synonyms: [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid benzyl ester;[1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid benzyl ester;1-(4-Chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeurebenzylester;[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-indol-3-yl]-acetic acid benzyl ester;2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid benzyl ester
• CAS NO: 26001-79-6
• Molecular Formula: C26H22ClNO4
• Molecular Weight: 447.918
• Mol File: 26001-79-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 552.4±50.0 °C(Predicted)
• Density: 1.23±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, phenylmethyl ester(26001-79-6)
• EPA Substance Registry System: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, phenylmethyl ester(26001-79-6)

Safety Data

• Hazardous Substances Data: 26001-79-6(Hazardous Substances Data)

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 3285-40-3 (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid benzyl ester 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 76812-83-4 6-Nitro-1-(4-chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeurebenzylester 
• 76812-82-3 4-Nitro-1-(4-chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeurebenzylester 
• 344238-45-5 4-Nitro-1-(4-chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeure 
• 344238-44-4 6-Nitro-1-(4-chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeure 

Relevant articles and documents

Design and synthesis of indomethacin analogues that inhibit P-glycoprotein and/or multidrug resistant protein without Cox inhibitory activity

We designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug resistance indicated that NSAIDS modulation of multidrug-resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities.

Synthesis and biological evaluation of ester derivatives of indomethacin as selective COX-2 inhibitors

The ester derivatives of indomethacin were prepared by condensing indomethacin with an equimolar quantity of an appropriate alcoholic compound in anhydrous dichloromethane in the presence of DCC and DMAP. Spectral studies comprising of IR, 1H NMR, mass, and microanalysis were performed in order to confirm their structures. In vivo anti-inflammatory studies were carried out using carrageenan rat paw edema method and in vivo ulcerogenic studies by ulcer index method for the panel of synthesized compounds. Out of eleven compounds, the compound IIc displayed moderate anti-inflammatory activity with no observable ulcerogenic effect when compared to indomethacin. Furthermore, compound IIc, indomethacin and celecoxib were tested at a concentration of 20 μM against COX-1 and COX-2 enzymes by colorimetric COX inhibitor screening assay. Compound IIc was found to be active against COX-2 and COX-1 enzymes exhibiting 62.0 and 12.9% inhibition, respectively. Springer Science+Business Media, LLC 2011.

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.