ChemInform Abstract: METABOLIC CONVERSION OF BENZO(A)PYRENE BY SYRIAN HAMSTER LIVER MICROSOMES AND BINDING OF METABOLITES OF DEOXYRIBONUCLEIC ACID

Abstract

Aus Benzo(a)pyren (Ia) werden die Metaboliten (Ib), (Ic), (II), (III) sowie (IVa) und (IVb) erhalten und in ihrer Struktur bestätigt.

Stereochemical course in reactions between nucleophiles and arene oxides

“…nm (c 3645); pmr (CH3) 3.47, (OH) 2.88, (H, and H6) 4.08 and 4.55, (H2_5) 5.95 (broad s) with _6 = 10.5; mass spectrum 127 (1), 126 (6), 109 (10), 108 (100), 95 (6), 94 (64), 93 (17), 79 (14), 78 (55), 77 (20), 68 (9), 67 (6), 66 (29). 65 (84), 64 (7), 63 (15), 62 (7), 61 (6), 55 (10), 51 (24), 50 (16), 41 (7), 40 (11), 39 (56), 38 (15), 37 (7).…”

“…Found: C, 66.60; H, 7.85. Catalytic reduction of 10a at atmospheric pressure with 10 % Pd/C catalyst gave trans-2-methoxycyclohexanol, the structure of which was established by comparison of the ir and mass spectrum with that of an authentic sample prepared as reported previously.48 ZraA«-6-Methoxycyclohexa-2,4-dien-l-yl acetate was prepared as a colorless liquid in 94 % yield (short-path distillation) from reaction of 10a with acetic anhydride in pyridine: ir (CHC13) 3020, 2980, 2810, 1735, 1455, 1410, 1370, 1295, 1225, 1100, 1080, 1020, 995, 945 and 900 cm'1; uv max (95% C2H6OH) 259 nm (e 4470); pmr (CH3C(=0)-) 2.13, (CH3O) 3.47, (He) 4.17, (Hi) 5.70, (H2_5) 6.05 with -e = 7; mass spectrum 136 (4), 133 (3), 109 (10), 108 (100), 94 (21), 93 (16), 79 (16), 78 (56), 77 (19), 65 (71), 63 (13), 51 (21), 50 (13), 45 (22), 44 (34), 43 (28), 39 (38), 38 (10).…”

“…The filtrate and combined washes were dried, filtered, and evaporated to give a yellow oil that was distilled under high vacuum (0.05 mm, pot temp 60°) to yield 631 mg (60%) of a colorless oil that crystallized in the receiver. Recrystallization from etherpentane gave /ra/w-2-amino-3,5-cyclohexadien-l-ol as glistening white needles: mp 62.0-63.5°; ir (CHC13) 3580, 3460, 2980, 2910, 2840, 1580, 1410, 1080, 1015, and 890 cm'1; Xmax(CH3OH) 260 nm (e 2731); pmr (NH2 and OH) 2.80 (exchangeable), (H2) 3.50, (Hi) 4.18, (H3_6) 5.85 with -2 = 12; mass spectrum 112 (2), 111 (36), 94 (17), 93 (38), 82 (45), 80 (12), 69 (14), 68 (13), 67 (19), 66 (42), 65 (27), 59 (31), 56 (14), 55 (14), 54 (13), 44 (14), 43 (100), 42 (14), 41 (22), 40 (11), 39 (38); M+ caled 111.06841, found 111.06818.…”

“…The mixed stereochemistry of solvolytic products formed under acid conditions may be more representative of this latter type of mechanism.21 •22 The binding of Kregion arene oxides, as well as phenols, dihydrodiols, and the parent polycyclic hydrocarbons, to DNA, RNA, and protein has been studied extensively. [37][38][39][40][41] As is the case for other alkylating agents,42•43 the oxides were found to be more reactive toward the purine bases, especially guanine. Information on the chemical nature of this binding has yet to be reported.…”