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Structure and Photochemical Behavior of the Cyclodextrin Inclusion Complexes of the Benzoylthiophene‐Derived Drugs Tiaprofenic Acid (=5‐Benzoyl‐ α ‐methylthiophene‐2‐acetic Acid) and Suprofen (= α ‐Methyl‐4‐(2‐thienylcarbonyl)benzeneacetic Acid)
Author(s) -
Monti Sandra,
Encinas Susana,
Lahoz Agustin,
Marconi Giancarlo,
Sortino Salvatore,
PerezPrieto Julia,
Miranda Miguel A.
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010919)84:9<2452::aid-hlca2452>3.0.co;2-t
Subject(s) - chemistry , cyclodextrin , excited state , circular dichroism , photochemistry , carboxylate , acetic acid , reactivity (psychology) , photodegradation , stereochemistry , medicinal chemistry , organic chemistry , catalysis , photocatalysis , medicine , physics , alternative medicine , pathology , nuclear physics
The effect of β ‐cyclodextrin ( β ‐CD) on the excited‐state reactivity of the two benzoylthiophene derivatives, tiaprofenic acid (TPA; 2 ) and suprofen (SPF; 3 ) in their carboxylate forms is studied. The presence of β ‐cyclodextrin does not affect the nature of the photoproduced transients and the photoproducts, but increases the photodegradation quantum yields of both drugs. The efficiency of the photodecarboxylation process is enhanced. This effect is rationalized in the light of the inclusion of 2 and 3 in the β ‐CD cavity, affecting the energy of the lowest excited states of the drugs. The structure of the complexes is determined by induced circular dichroism, and molecular‐mechanics and dynamic Monte Carlo calculations. The photoreactivity of the decarboxylated photoproduct 7 of tiaprofenic acid ( 2 ) in presence of β ‐CD is also examined.