A study of chemical carcinogenesis. 84. Synthesis and fluorescence spectra of structural analogs of potential benzo[b]fluoranthene-DNA adducts

Chemical Carcinogenesis. Part 151. Synthesis of Fjord Region Diol Epoxides as Potential Ultimate Carcinogens of Dibenzo[a,l]pyrene

“…MS I-(9-Phenanthryl)-2-(2-methoxyphenyl)ethylene (1). A solution of 9-(bromomethyl)phenanthrene (12) (43.5 g, 160 mmol) and triphenylphosphine (49.0 g, 180 mmol) in 300 mL of toluene was heated under reflux for 3 h. The reaction mixture was cooled, and the phosphonium salt (76.0 g, 90 %) was isolated by filtration. To a stirred solution of the salt (30.0 g, 56.2 mmol) and o-anisaldehyde (5.10g, 37,4 mmol) in 290 mL of MeOH was added NaOMe (3.40 g, 56.2 mmol).…”

“…This was prepared from 8 in 84% yield as described for 10: mp 234-236 °C; IR (KBr) 3049, 2925, 2856,1697,1663,1589,1549,1431,1275,1244,909,764,749,651, 603,583 cm-1; NMR 6.55 (d, 1H, Hu, «/13,u = 10.5 Hz), 7.62 (dd, 1H, Ha, «/a,3 = e/1,2 = 8.2 Hz), 7.85 (dd, 1H, H3,1/2,3 = e/3,4 = 8.2 Hz), 8.05-8.15 (m, 3H, He, H8, and H9), 8.20 (d, 1H, H7, «/8,7 -7.2 Hz), 8.28 (d, 1H, Hi, «/i,2 -8.2 Hz), 8.45 (d, 1H, Hu,«/13,14 = 10.5 Hz), 8.80 (d, 1H, H4, J3,4 = 8.2 Hz), 8.85 (s, 1H, Hu), 8.88 (d, 1H, Hs, </s,e = 7.4 Hz); MS (m/z, relative intensity) 334 (M+, 20), 332 (30), 304 (100); high-resolution MS, caled for C24H12O2 (M+) 332.0837, found 332.0841. DB[a,7]P-ll,12-diol (12). To a stirred suspension of 11 (50.0 mg, 0.15 mmol) in absolute ethanol (100 mL) was added 200 mg (5.38 mmol) of NaBH4 in portions.…”

“…The organic phase was washed with H2O, dried (Na2S04), and concentrated. The resulting yellow residue was purified by chromatography on Florisil with elution by CHaCla/EtOAc (50:50) to give pure diol 12 (35 mg, 69%): mp 190-192 °C; IR (KBr) 3412, 3222, 3049, 2924,2853,1446,1194,1072,748,649,581 cm-1; NMR 4.58-4.62 (m, 1H, Hu), 4.72 (d, 1H, Hn, Ju.u = 10.5 Hz), 6.30 (dd, 1H, Hu, =/13,14 = 10.1 Hz, J12,13= 2.1 Hz), 7.27 (d, 1H, Hu, «/13,14 = 10.1 Hz), 7.71-7.80 (m, 2H, H2 and H3), 8.08-8.17 (m, 3H, He, H", and H9), 8.26 (d, 1H, H7, =/6>7 = 7.5 Hz), 8.43 (s, 1H, Hu), 8.53 (d, 1H, Hi, </i,2 = 9.1 Hz), 8.95-9.05 (m, 2H, H4 emd Hs); MS (m/z, relative intensity) 346 (M\ 70), 318 (60), 289 (100).…”

Fluoranthene-based triarylamines as hole-transporting and emitting materials for efficient electroluminescent devices

“…It is interesting to note that the data is not significantly different from those observed for the basic unit fluoranthene (289 and 360 nm). 27 It suggests that outer phenyl rings do not extend the conjugation of the core dramatically. This is possibly due to the twisting of the phenyl groups out of the plane of the aromatic p-system which inhibits an effective p-conjugation with the fluoranthene core (see below for theoretical results).…”

Bacterial and Human Cell Mutagenicity Study of Some C 18 H 10 Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons Associated with Fossil Fuels Combustion

“…Compounds 5 and 6 (ratio 1:6) were isolated as a white powder ( Acephenanthren-4-one 7andAcephenanthren-5-one (8). A mixture of crude compounds 5 and 6 (12.5 g, 53 mmol) was cyclized according to the procedure ofAmin et al (40). After work-up and column chromatography (silica; CH2CI2/ petroleum ether 3:1), 5.0 g (44%) of a yellow mass was obtained, consisting of compounds 7 and 8 in a ratio of 4:1.…”