Premium
Photooxidation of Troglitazone, a New Antidiabetic Drug *
Author(s) -
Fu Yulan,
Sheu Chimin,
Fujita Takashi,
Foote C. S.
Publication year - 1996
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1996.tb05664.x
Subject(s) - troglitazone , chemistry , singlet oxygen , reactivity (psychology) , quinone , acetone , photochemistry , oxygen , quenching (fluorescence) , reaction rate constant , medicinal chemistry , stereochemistry , organic chemistry , fluorescence , kinetics , medicine , peroxisome , biochemistry , physics , alternative medicine , pathology , quantum mechanics , gene
Troglitazone (CS‐045) is a new oral antidiabetic drug reported to be effective in insulin‐resistant diabetes and to show antihypertensive effects. Photooxidation of troglitazone gave the quinone and quinone epoxide as the major final stable products. An intermediate observed by NMR spectroscopy was shown to be the hydroperoxydi‐enone, which is moderately stable at room temperature. The rate constant of singlet oxygen quenching by troglitazone is 2.14 × 10 8 M −1 s −1 and the reaction rate constant in acetone‐d, is 8.64 × 10, M −1 s −1 . Only the chroman ring of troglitazone reacts with and quenches singlet oxygen significantly, and its reactivity and products are analogous to those of a‐tocopherol. The reactivity of CS‐045 toward singlet oxygen is much larger than that of the related compounds lacking the chroman ring.