[reaction: see text] A new spirocyclic diol, 9,9'-spirobixanthene-1,1'-diol, was synthesized in two steps from readily available starting material m-phenoxyanisole. Resolution of the racemic diol was achieved by cocrystallization with N-benzylcinchonidinium chloride and N-benzylquininium chloride in acetonitrile. The corresponding spiro monodentate phosphoramidite ligand has been prepared for R...

Addition of benzamide (BZ) at the onset of S phase inhibited expression of the neoplastic phenotype in human foreskin fibroblasts treated in vitro with (+/-)-7 alpha,8 beta-dihydroxy-9 beta,10 beta-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (B[a]P diol epoxide) in early S phase. Analysis of the specific B[a]P diol epoxide-DNA adducts revealed that ca. 65% of the total adducts in BZ and non-BZ carc...

The nature of the CD-active species obtained by mixing dimolybdenum tetraacetate and a chiral 1,2-diol in DMSO has been studied by different techniques (1D and 2D (1)H NMR, CD, UV/Vis) with two substrates, (R)-phenyl-1,2-ethanediol (1) and (R,R)-butane-2,3-diol (2). The diol/dimolybdenum adducts have diagnostic CD spectra whose sign correlates with the absolute configuration of the organic subs...

The mutagenic activities of the enantiomers of the pair of diastereomeric bay-region benzo(c)phenanthrene 3,4-diol-1,2epoxides were evaluated in histidine-dependent strains of Sal monella typhimurium and in an 8-azaguanine-sensitive Chinese hamster Å“il line. In strains TA 98 and TA 100 of S. typhimurium, the range in mutagenic activity observed for the four optically active isomers was less th...

BACKGROUND The chemistry of tetralin-1,4-dione, the stable tautomer of 1,4-dihydroxynaphthalene, has not been explored previously. It is readily accessible and offers interesting opportunities for synthesis. RESULTS The title reactions were explored. L-Selectride reduced the diketone to give preferentially the cis-diol (d.r. 84 : 16). Red-Al gave preferentially the trans-diol (d.r. 13 : 87). ...

The biotransformation of partheniol by the fungus Calonectria decora ATCC 14767, produced six metabolites. These metabolites are; aromadendr-1(10)-en-8alpha -ol; 5(9),6-tricyclohumul-1(10)-en-8alpha-ol; 4,15-didehydro-6-bicyclohumulan-8a,10alpha-diol; 5(9),6-tricyclohumulan-4a,8alpha-diol; maalian-la,8alpha-diol and 14-epi-1(4)-epoxymaalian-8alpha-ol. The identities of these metabolites were es...

The mutagenic activities of benz(a)acridine, benz(c)acridine, and a number of their derivatives, including 12 epoxides and diol-epoxides, were examined in bacterial and mammalian cells to determine the importance of bay-region activation of azapolycyclic aromatic hydrocarbons. In Salmonella typhimurium strain TA98, the diastereomeric bay-region 3,4-diol-1,2-epoxides of benz(c)acridine, in which...

Riboflavin 5'-phosphate (flavin mononucleotide; FMN) inhibits the mutagenicity of (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (B[a]P diol epoxide), the only known ultimate carcinogenic metabolite of benzo[a]pyrene. Coincubation of 10, 25, and 50 nmol of FMN with strain TA100 of histidine-dependent Salmonella typhimurium inhibits the mutagenicity of ...

The source of NADPH-dependent cytosolic 3 -hydroxysteroid dehydrogenase (3 -HSD) activity is unknown to date. This important reaction leads e.g. to the reduction of the potent androgen 5 -dihydrotestosterone (DHT) into inactive 3 -androstanediol (3 -Diol). Four human cytosolic aldo-keto reductases (AKR1C1– AKR1C4) are known to act as non-positional-specific 3 -/ 17 -/20 -HSDs. We now demonstrat...