287118-98-3

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Nitroaspirin (NCX 4016)

InChI:InChI=1/C16H14O5/c1-11(18)20-15-8-3-2-7-14(15)16(19)21-13-6-4-5-12(9-13)10-17/h2-9,17H,10H2,1H3

Upstream product

• 203065-55-8 2-(acetyloxy)benzoic acid 3-(formyl)phenyl ester 
• 50-78-2 aspirin 
• 620-24-6 3-Hydroxybenzyl alcohol 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 100-83-4 meta-hydroxybenzaldehyde 

Downstream Products

• 1345092-34-3 3-(((1-chloroethoxy)carbonyloxy)methyl)phenyl 2-acetoxybenzoate 
• 1345091-95-3 3-(((1-(nitrooxy)ethoxy)carbonyloxy)methyl)phenyl 2-acetoxybenzoate 
• 175033-36-0 2-(acetyloxy)benzoic acid 3-[(nitrooxy)methyl]phenyl ester 
• 287118-99-4 2-(acetyloxy)benzoic acid 3-(chloromethyl)-phenyl ester 

Relevant academic research and scientific papers

Nitric Oxide Releasing Prodrugs of Therapeutic Agents

The present invention relates to nitric oxide releasing prodrugs of known drugs or therapeutic agents which are represented herein as compounds of formula (I) wherein the drugs or therapeutic agents contain one or more functional groups independently sele

Chemical insights in the concept of hybrid drugs: The antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin

Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to current beliefs, neither ASA nor NO contributes to this antitumor effect. Rather, an unsubstituted QM was identified as the sole cytotoxic agent. QM forms from 1 after carboxylic ester hydrolysis and, in accordance with the HSAB theory, selectively reacts with cellular GSH, which in turn triggers cell death. Remarkably, a derivative lacking ASA and the -ONO 2 group is 10 times more effective than 1. Thus, our data provide a conclusive molecular mechanism for the antitumor activity of 1. Equally importantly, we show for the first time that a "presumed invisible" linker in a hybrid drug is not so invisible after all and is in fact solely responsible for the biological effect.

Process for obtaining (nitroxymethyl)phenyl esters of salicylic acid derivatives

A process for obtaining (nitroxymethyl)phenyl esters of salicylic acid derivatives of formula (I) wherein R1is the OCOR3group characterized in that it comprises the following steps: a) reaction of a halide of a salicylic acid derivative with hydroxybenzylacohol in the presence of a base: b) nutration of the obtained product in anhydrous conditions by a mixture of nitric acid with a different inorganic acid, or an organic acid, or an anhydride of one or two organic acids: c) recovery of the final product.

Nitric oxide-donating non-steroidal anti-inflammatory drugs: The case of nitroderivatives of aspirin

Nitric oxide (NO) acts as a key signalling mechanism in a number of cells and tissues in the mammalian organism. Modulation of the biosynthesis of NO has emerged to be relevant to the treatment of a variety of human diseases. In the attempt to reduce the serious side effects of non-steroidal anti-inflammatory drugs (NSAIDs), especially in the gastrointestinal tract, a NO-releasing moiety has been linked to conventional NSAIDs. A prototypical example is that of NO-releasing derivatives of aspirin. Thanks to the cytoprotective action of NO such compounds do not produce gastric damage and are emerging as an interesting novel group of drugs for their unique pharmacological properties.