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Novel 8‐hydroxy‐3‐phenoxazinone derivatives related to the actinomycin D chromophore
Author(s) -
Sehgal Raj K.
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001228
Subject(s) - chromophore , chemistry , alkyl , derivative (finance) , halide , alkylation , dna , product (mathematics) , stereochemistry , photochemistry , organic chemistry , biochemistry , catalysis , financial economics , geometry , mathematics , economics
A reexamination of the reaction of the model actinomycin D chromophore ( 1a ) with DDQ revealed the presence of hitherto unknown 8‐hydroxy‐substituted phenoxazinone derivative 1c as a minor product along with the 7‐hydroxy derivative 1b as the major product. Further, the isomeric hydroxy derivatives can be conveniently converted by reaction with suitable alkyl halides to afford the corresponding alkylated products with suitable alkylating species for interaction of the actinomycin D chromophore with DNA of the cell.