Reactions of amino-substituted cyclodextrins with 2-arylpropanoic acid derivatives
Reactions of 6A-amino-6A-deoxy-β-cyclodextrin and 3A-amino-3A-deoxy-(2AS,3 AS)-β-cyclodextrin with the 3-nitrophenyl esters of 2-phenylpropanoic acid and Ibuprofen occur with only low diastereoselectivity, to afford the corresponding arylpropanamido-substituted cyclodextrins. These amides are also formed by decarboxylation of corresponding malonates, again with only low diastereoselectivity. The n.m.r. spectra of the amido-substituted cyclodextrins indicate that the aryl substituent is included within the cyclodextrin annulus at low temperature, but becomes dissociated from the cavity as the temperature is increased.
Easton, Christopher J.,Lincoln, Stephen F.,May, Bruce L.,Papageorgiou, John
p. 451 - 456
(2007/10/03)
Ester and amide prodrugs of ibuprofen and naproxen: Synthesis, anti- inflammatory activity, and gastrointestinal toxicity
Ester and amide prodrugs of ibuprofen (1) and naproxen (16) were synthesized and evaluated for anti-inflammatory activity and gastrointestinal toxicity. The chemical structure of the prodrugs was varied in terms of lipophilicity and reactivity toward hydr
Shanbhag,Crider,Gokhale,Harpalani,Dick
p. 149 - 154
(2007/10/02)
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