154271-40-6

Basic information

• Product Name: chloromethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
• Synonyms: chloromethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
• CAS NO: 154271-40-6
• Molecular Weight: 406.265
• Mol File: 154271-40-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: chloromethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: chloromethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate(154271-40-6)
• EPA Substance Registry System: chloromethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate(154271-40-6)

Safety Data

• Hazardous Substances Data: 154271-40-6(Hazardous Substances Data)

Upstream product

• 49715-04-0 chlorosulfuric acid chloromethyl ester 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 

Downstream Products

• 955130-64-0 C₂₈H₂₉ClN₄O₁₀ 
• 1402916-78-2 3-carbamoyl-1-((2-(-1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetoxy)methyl)pyridine-1-ium iodide 
• 955130-64-0 O₂-(acetoxymethyl) 1-{2-[2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxymethyloxycarbonyl]pyrrolidin-1-yl}diazen-1-ium-1,2-diolate 

Relevant articles and documents

Second-generation aspirin and indomethacin prodrugs possessing an O 2-(acetoxymethyl)-1-(2-carboxypyrrolidin-1-yl)diazenium-1,2-diolate nitric oxide donor moiety: Design, synthesis, biological evaluation, and nitric oxide release studies

The carboxylic acid group of the anti-inflammatory (AI) drugs aspirin and indomethacin was covalently linked to the 1-(2-carboxypyrrolidin-1-yl)diazen-1- ium-1,2-diolate ion via a one-carbon methylene spacer to obtain two new hybrid prodrugs. The aspirin prodrug (23) was a 2.2-fold more potent AI agent than aspirin, whereas the indomethacin prodrug (26) was about 1.6-fold less potent than indomethacin. Prodrugs 23 and 26 slowly released nitric oxide (NO) upon dissolution in phosphate buffer at pH 7.4 (1.1 mol of NO/mol of compound after 43 h), but the rate and the extent of NO release were higher (1.9 mol of NO/mol of compound in 3 min or less) when the compounds were incubated in the presence of porcine liver esterase. In vivo ulcer index (UI) studies showed that the aspirin prodrug 23 (UI = 0.7) and indomethacin prodrug 26 (UI = 0) were substantially less ulcerogenic than the parent drugs aspirin (UI = 51) and indomethacin (UI = 64).