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Methoxy‐ and acetoxy‐8‐oxoberbines ‐ synthesis, antitumor activity, and interaction with DNA
Author(s) -
Weimar Christian,
Angerer Silvia Von,
Wiegrebe Wolfgang
Publication year - 1991
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.2503240810
Subject(s) - chemistry , dna , in vitro , ether , intercalation (chemistry) , cleavage (geology) , dna synthesis , acetylation , stereochemistry , cell growth , cell culture , biochemistry , organic chemistry , biology , paleontology , genetics , fracture (geology) , gene
Most of the methoxy‐8 H ‐dibenzo[ a,g ]isoquinolin‐8‐ones 3a‐h and their acetoxy derivatives 6a‐e were synthesized by condensation of 1‐oxo‐1,2,3,4‐tetrahydroisoquinolines 4a‐c and homophthalic acid anhydrides 5a and b, ether cleavage and acetylation. These protoberberinones were tested for cytostatic activity in vitro using MDA‐MB‐231 mammary tumor cells and for interaction with native calf thymus DNA. Tetramethoxy‐8‐oxoberbine 3f shows an inhibition of cell proliferation of 87% at a concentration of 10 −5 mole; its cytostatic effect does not depend on intercalation into DNA.