ISSN:
0170-2041
Keywords:
Benzofurans
;
Singlet oxygen
;
Photooxygenation
;
Dioxetanes
;
Mutagenicity
;
Ames test
;
Salmonella typhimurium
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Tetraphenylporphine-sensitized photooxygenation of benzofuran derivatives 1 afforded the corresponding benzofuran dioxetanes 2 in good yields. Allylic hydroperoxides 3 were formed regioselectively from 2,3-dimethyl-substituted benzofurans as minor products, except in the case of the benzofuran 1d, which gave predominantly the hydroperoxide 3d. The relative reactivities of the benzofurans toward singlet oxygen depended on the nature of substituents at the C-2 and C-3 positions of the furan rings. The benzofuran dioxetanes 2 were strongly mutagenic in the Salmonella typhimurium strain TA 100, their mutagenicity depending on the type of substituents of the dioxetane and of the benzo rings.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199119910106
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