114326-33-9

Usage

InChI:InChI=1/C26H20O4/c1-15(27)29-25-12-11-21-22(26(25)30-16(2)28)10-9-19-13-18-8-7-17-5-3-4-6-20(17)23(18)14-24(19)21/h3-14,25-26H,1-2H3/t25-,26-/m0/s1

Upstream product

• 114326-28-2 3-methoxy-14-acetoxydibenzanthracene 
• 114326-26-0 7-Methoxy-3-naphthalen-2-yl-3H-naphtho[1,2-c]furan-1-one 
• 114326-27-1 6-Methoxy-2-naphthalen-2-ylmethyl-naphthalene-1-carboxylic acid 
• 114326-31-7 dibenzanthracene-3,4-dione 
• 114326-25-9 6-methoxy-1-naphthoic acid diethylamide 
• 83136-28-1 3-methoxydibenzanthracene 
• 83136-32-7 3-hydroxydibenzanthracene 
• 114326-32-8 Acetic acid (3S,4S)-3-acetoxy-3,4-dihydro-dibenzo[a,j]anthracen-4-yl ester 
• 137676-23-4 (-)-(3S,4S)-trans-3-bromo-1,2,3,4-tetrahydrodibenzanthracen-4-ol 
• 137676-26-7 (-)-(3R,4R)-trans-1,2,3,4-tetrahydrodibenzanthracen-3,4-diol 
• 137676-28-9 (-)-(3R,4R)-trans-1-bromo-1,2,3,4-tetrahydrodibenzanthracen-3,4-diyl diacetate 
• 137676-27-8 (-)-(3R,4R)-trans-1,2,3,4-tetrahydrodibenzanthracen-3,4-diyl diacetate 
• 137676-25-6 (-)-(3R,4S)-3,4-epoxy-1,2,3,4-tetrahydrodibenzanthracene 
• 114326-32-8 (-)-(3R,4R)-trans-3,4-dihydrodibenzanthracen-3,4-diyl diacetate 

Downstream Products

• 114326-34-0 (+/-)-trans-3,4-dihydroxy-syn-1,2-epoxy-1,2,3,4-tetrahydrodibenz[a,j]anthracene 

Relevant academic research and scientific papers

Synthesis of the Mammalian Metabolites of Dibenzanthracene: Dibenzanthracene 3,4-Oxide and (-)-(3R,4R)-trans-3,4-Dihydroxy-3,4-dihydrodibenzanthracene

Dibenzanthracene 3,4-oxide (2) and the isomeric oxepine (19) were synthesised simultaneously from a common dibromoester precursor (9).The oxepine isomer (19) was also formed by photoisomerisation of the arene oxide (2).Resolution and absolute configuration assignment of each enantiomer of trans-3-bromo-4-hydroxy-1,2,3,4-tetrahydrodibenzanthracene (10) was achieved by chromatographic separation and recrystallisation of the MTPA diastereoisomers (11a/11b).The (+)-(3S,4S)bromo-MTPA ester (11a) was used in a seven-step synthesis of the chiral metabolite (-)-(3R,4R)-trans-3,4-dihydroxy-3,4-dihydrodibenzanthracene (3).The (-)-(3R,4R)-bromo-MTPA ester diastereoisomer (11b) similarly served as a precursor of (3S,4R)-dibenzanthracene 3,4-oxide (2) which spontaneously racemised via an unstable oxepine isomer (18).

Synthesis of the Tumorigenic 3,4-Dihydrodiol Metabolites of Dibenzanthracene and 7,14-Dimethyldibenzanthracene

Synthses are described of the trans-3,4-dihydrodiol derivatives (2a and 2b) of dibenzanthracene and 7,14-dimethyldibenzanthracene (1a and 1b), implicated as their proximate carcinogenic metabolites.Conversion of 2a to the bay region anti-diol epoxide derivative 3a, its putative ultimate carcinogenic metabolite, is also reported.The related diol epoxide derivative of 2b could not be prepared due to its chemical instability.Tumorigenicity assays confirm that 1b and 2b are potent carcinogens on mouse skin, while 1a and 2a are only relatively weakly active.The diol epoxide 3a exhibited significantly higher tumorigenicity than its dihydrodiol precursor 2a.These findings are consistent with the hypothesis that the bay region diol epoxide metabolites are the active carcinogenic forms of these hydrocarbons.They also support the generalization that methyl substitution in bay regions enhances the carcinogenic activity of polycyclic aromatic hydrocarbons.