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[reaction: see text] A new method for the generation of highly reactive benzyl cations by thermal decomposition of aryl-benzyl-sulfamoylcarbamates, obtained in a one-pot reaction from chlorosulfonyl isocyanate, is described. The generated cations alkylate aromatic compounds efficiently in the absence of catalysts.
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The in vivo metabolism and excretion of benzyl acetate (BA), a model compound for glycine conjugation, was examined in male Fischer 344 rats and C57BL/6N mice. Rats aged 3-4, 9, and 25 months received a single oral dose of either 5 or 500 mg/kg 14C-BA, while male mice aged 2, 13, and 25 months received a single oral dose of 10 mg/kg 14C-BA. Urine and feces were collected for 96 hr. Biliary excretion and plasma elimination were also examined in male Fischer rats after iv administration of 5 mg/kg 14C-BA. In both young and old rats and mice, hippuric acid (HA) was the major urinary metabolite after oral dosing of BA. No significant age-related difference was observed in rats in the urinary elimination of BA-derived radioactivity or in the percentage of the total dose excreted as hippuric acid (approximately 95%). Twenty-five-month old rats excreted a significantly higher percentage of the total dose as benzyl mercapturic acid (approximately 2%) than did 3- to 4-month-old rats (approximately 1%) at the 5 mg dose. Benzyl mercapturic acid excretion in 3- to 4-month-old rats was also increased significantly at 500 mg/kg BA vs. 5 mg/kg BA. Fecal excretion of BA-derived radioactivity declined significantly in 25-month-old rats at both the 5 and 500 mg dose. This decrease was reflected by an age-related decline in biliary excretion and higher plasma levels of BA-derived radioactivity. Examination of plasma metabolites revealed a significantly higher level of HA and benzoyl glucuronide in 25-month rats.(ABSTRACT TRUNCATED AT 250 WORDS)
Molecular structure, spectroscopic and photophysical data for the singlet state of 3-benzyl-lumiflavin in different solvents are presented. Theoretical studies concerning singlet-singlet and triplet-triplet excitation energies were carried out using time-dependent density functional theory (TD-DFT) calculations. These predictions are in good agreement with the experimental results, which reflect the solvent interactions. All the observable singlet-singlet transitions have pi-pi* character. The title compound appears to be an efficient sensitizer of the production of singlet oxygen (phi(Delta)= 0.53). The crystal structure of 3-benzyl-lumiflavin is also presented, along with its solid-state photophysical data.
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Unsymmetrically substituted N-nitrosomethylbenzylamine is an oesophageal carcinogen with potential methylating and benzylating properties. Whereas the methylating activity of the compound has been investigated, little is known of its potential benzylating properties. In order to elucidate the biological consequences of benzylation, related model compounds which are presumed benzylating agents were synthesized and tested for mutagenicity. N-nitrosobenzylurea and its structural analogue N-nitroso-p-methylbenzylurea were direct acting mutagens in Salmonella typhimurium TA 98. Activity was also present in TA 1535, but it was less pronounced. N-nitroso-alpha-acetoxybenzyl-benzylamine was equally mutagenic in S. typhimurium TA and TA 1535. N-nitroso-acetoxymethyl-benzylamine and N-nitrosoacetoxy-methyl-p-methylbenzylamine are two model compounds which may decompose by hydrolysis or through esterases to yield intermediates also though to arise after alpha-C hydroxylation of the methyl group of the parent nitrosamines. These compounds needed additional activation by enzymes present in the post-mitochondrial supernatant of rat liver. They were distinctly mutagenic in TA 98. Furthermore, all compounds also caused the induction of phage lambda in a qualitative assay with Escherichia coli Br 513. Thus, benzylation of DNA clearly results in a biological consequence. These findings are supportive of the theory that if enzymic attack occurs on the methyl group of N-nitrosomethylbenzylamine, benzylation may also contribute to the overall biological activity of the compound.
The synthesis and structure--activity profile of 2-substituted benzimidazol-4-ols as inhibitors of cell-free RBL-1 5-lipoxygenase are discussed, and their potency is compared with that of the standard inhibitors phenidone, AA 861, BW 755C, and nordihydroguaiaretic acid. In contrast to the standard compounds, most did not inhibit the release of slow-reacting substance of anaphylaxis (SRS-A) in vivo when administered at 200 microM ip to rats subjected to peritoneal anaphylaxis, although five compounds containing a methoxylated benzyl group (compounds 36, 39, 42, and 43) or hydroxylated benzyl group (41) showed similar activity to that of phenidone, nordihydroguaiaretic acid, and AA 861. Of the many compounds tested, two, 5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol (57) and 2-(4-methoxybenzyl)-7-methyl-1H-benzimidazol-4-ol (36), like dexamethasone, inhibited monocyte accumulation in a pleural exudate model of inflammation. Standard lipoxygenase inhibitors such as phenidone, BW 755C, and AA 861 were inactive in this system.
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Fourth instar larvae of Culex pipiens were exposed to six benzyl-1,3-benzodioxole derivatives to assess the effectiveness of these compounds as anti-juvenile hormone agents. Mortality ranging from between 18 and 99% was observed in larvae and early pupae but the surviving adults showed no clearly defined anti-juvenile hormone effects. Adult effects included a reduction in number of eggs developed and the presence of degenerating eggs 4 days after the blood meal.
By reaction of 3-chloro-1,2-benzisothiazole with phenylacetonitrile, 3-benzyl-1,2-benzisothiazole derivatives can be obtained. These compounds seem to mimic the benzylisoquinoline structure so they can exhibit spasmolytic activities. Both antimuscarinic and direct muscle-relaxant properties have been found with N,N-dimethyl-3-phenyl-3-(1,2-benzisothiazol-3-yl) propylamine hydrochloride.
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