96334-91-7Relevant academic research and scientific papers
9-anthryloxyaminoalkanes and related compounds as anti-inflammatory and analgetic agents
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, (2008/06/13)
Compounds useful for treating inflammation, pain and swelling, represented by the formula: STR1 and the pharmaceutically acceptable acid addition salts thereof, wherein: Y and Z are each independently halo, alkyl or alkoxy; l and m are each independently integers of 0-4; b is an integer of 2-12; and X is selected from the group consisting of: --NR1 R2, --NR1 (CH2 CH2 OH), STR2 in which R1 and R2 are independently H, alkyl or cycloalkyl; R3 is H, alkyl or CH2 CH2 OH; and n is an integer of 3-7.
Facile Aryl Ether Hydrolysis: Kinetics and Mechanism of 9-Anthryl Ether Cleavage in Aqueous Solution
Powell, Michael F.
, p. 56 - 61 (2007/10/02)
The hydrolysis rates of anthryl ether, 4-(9-anthroxy)butylamine (1), have been determined in aqueous solution from pH 1 to 12 and 25 to 80 deg C, wherein it was found that this ether reacted significantly faster than other aryl ethers.The observed rate constants varied with pH according to eq 1 and values for kH+, kO, kN, and Ka (1) have been evaluated.At low pH, hydrolysis of 1 is characterized by general acid catalysis with carboxylic acid buffers (α = 0.61 +/- 0.06) and a solvent isotope effect of 1.85 +/- 0.09 at 25 deg C.Further, the product deut erium isotope effect for reaction of 1 and H+ is ca.3 and, when the reaction is carried out in 18O water, the anthrone reaction product contains exlusively 18O.These observations show unequivocally that acid hydrolysis occurs by rate-determining proton transfer to the 10-position of the anthracene moiety, followed by rapid reaction of water at the 9-position of the oxonium ion intermediate.The acid-catalyzed hydrolysis of 1 was thus found to resemble vinyl ether hydrolysis (i.e., an A-SE2 mechanism) instead of an A-2 mechanism shown by most other aryl ethers, such as anisole.
