97609-58-0

Upstream product

• 49715-04-0 chlorosulfuric acid chloromethyl ester 
• 50-78-2 aspirin 

Downstream Products

• 955130-63-9 C₁₈H₂₁N₃O₁₀ 
• 1248570-65-1 (2-acetyloxybenzoyl)oxymethyl 3-[3-(tert-butoxycarbonylamino)propanoyloxy]-4-(3-nitrooxypropoxy)benzoate 
• 1248570-73-1 (2-acetyloxybenzoyl)oxymethyl 3-[3-(tert-butoxycarbonylamino)propanoyloxy]-4-(3-nitrooxybutoxy)benzoate 
• 1248570-76-4 (2-acetyloxybenzoyl)oxymethyl 3-[2-(tert-butoxycarbonylamino)acetyl]oxy-4-(3-nitrooxypropoxy)benzoate 
• 1447760-32-8 (2-acetyloxybenzoyl)oxymethyl 3-[4-(tert-butoxycarbonylamino)butanoyloxy]-4-[3-nitrooxypropoxy]benzoate 
• 1447760-37-3 (2-acetyloxybenzoyl)oxymethyl 3-[3-(tert-butoxycarbonylamino)propanoyloxy]-4-(2,3-bisnitrooxypropoxy)benzoate 
• 1447760-38-4 (2-acetyloxybenzoyl)oxymethyl 3-hydroxy-4-(3-nitrooxypropoxy)benzoate 
• 1248570-50-4 (2-acetyloxybenzoyl)oxymethyl 3-(morpholin-4-ylmethyl)-4-[3-(nitrooxy)propoxy]benzoate 
• 1402916-77-1 1-((2-acetoxybenzoyl)oxy)-3-carboylpyridin-1-ium iodide 
• 955130-65-1 C₂₁H₁₉N₅O₁₂ 
• 955130-63-9 O-(acetoxymethyl) 1-[2-(acetylsalicyloyloxymethyloxycarbonyl)-pyrrolidin-1-yl]diazen-1-ium-1,2-diolate 
• 1144618-70-1 [(4-{[(3-aminocarbonyl-furoxan-4-yl)methyl]thio}benzoyl)oxy]methyl 2-(acetyloxy)benzoate 
• 1144618-68-7 [(4-{[(3-methyl-furoxan-4-yl)methyl]thio}benzoyl)oxy]methyl 2-(acetyloxy)benzoate 
• 1144618-64-3 [(4-{[2,3-bis(nitrooxy)propyl]thio}benzoyl)oxy]methyl 2-(acetyloxy)benzoate 

Relevant academic research and scientific papers

SUBSTITUTED METHYLFORMYL REAGENTS AND METHOD OF USING SAME TO MODIFY PHYSICOCHEMICAL AND/OR PHARMACOKINETIC PROPERTIES OF COMPOUNDS

The present invention relates to the synthesis and application of novel chiral/ achiral substituted methyl formyl reagents to modify pharmaceutical agents and/or biologically active substances to modify the physicochemical, biological and/or pharmacokinetic properties of the resulting compounds from the unmodified original agent.

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).