1421-80-3Relevant academic research and scientific papers
Synthesis and Properties of the Seven Isomeric Phenols of Dibenzanthracene
Platt, Karl L.,Oesch, Franz
, p. 5321 - 5326 (1982)
The seven possible monohydroxy derivatives of dibenzanthracene (4a-g) were synthesized by using the reductive cyclization of o-naphthoylnaphthoic acids with hydroiodic acid-red phosphorus.The mass, 1H NMR, and UV spectral properties are discussed in detail as a means of identifying metabolically formed phenols of dibenzanthracene.
Synthesis of Biologically Active Metabolites of Dibenzanthracene
Lee, Hong Mee,Harvey, Ronald G.
, p. 588 - 592 (2007/10/02)
Syntheses are described of the trans 1,2- and 3,4-dihydro diol metabolites (3a and 1a) of dibenzanthracene (DBA) and the corresponding diol epoxide derivatives 4 and 2, implicated as the ultimate carcinogenic metabolites of DBA.The synheses of 1a and 3a are accomplished from DBA via lithium-ammonia reduction to 1,4,7,8,11,14-hexahydrodibenzanthracene, base-catalyzed isomerization, Prevost reaction, dehydrogenation, and basic methanolysis.This approach involves considerably fewer steps and affords superior overall yields than obtainable by more conventional methods entailing multistep ring construction.Epoxidation of 1a affords stereospecifically the anti diol epoxide isomer 2, whereas similar reaction of 3a furnishes a mixture of the corresponding syn and anti diol epoxide isomers in 3:1 ratio.Biological evidence implicates 1a and 2 as proximate and ultimate carcinogenic forms, respectively, of DBA.Synthesis of 3-hydroxydibenzanthracene, also known to be a metabolite of DBA, is also described.
