The preparation of diamantanedicarboxylic acids with the carboxy groups at the tertiary carbon atoms of the diamantane skeleton is described. The procedure comprises bromination or oxidation of 1- and 4-diamantanecarboxylic acid and Koch-Haaf carboxylation of the reaction products. Of the four diamantanedicarboxylic acids synthesized, two - 1,4- and 1,7-diamantanedicarboxylic acids - have not been so far described.
1. Diamantane binds to liver microsomes from phenobarbital-treated rats with an apparent Ks value of 5.2 x 10(-7) mol/l. This value being lower than that obtained for perhydrophenanthrene indicates that diamantane is very strongly bound to microsomal cytochrome P-450. 2. Metabolic studies show that liver microsomes from phenobarbital-treated rats readily metabolize diamantane to mono-, di- and possibly tri-hydroxy derivatives, whereas liver microsomes from beta-naphthoflavone-induced rats do not bind this hydrocarbon or metabolize it. 3. Reconstituted cytochromes P-450 b and e were more efficient in the hydroxylation of diamantane than liver microsomes; metabolites formed by the reconstituted system do not include all the products formed by microsomes, which indicates the involvement of forms of cytochrome P-450 other than the isozymes b and e.
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