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PubMed2001

Photolysis of PAHs in aqueous phase by UV irradiation.

The photooxidation of polycyclic aromatic hydrocarbons (PAHs) was investigated in an aqueous ethanolic solution irradiated with a medium-pressure mercury lamp in laboratory photoreactors equipped with a quartz immersion well. Degradation photolysis of fluorene was more efficient than sensitized photolytic oxidation in the presence of TiO2 suspensions. Photolysis kinetics was dependent on molecular weight and the presence and type of substituents. During the photolytic degradation of fluorene and its derivatives, 9-fluorenone and its corresponding derivatives, which were more resistant to photolysis, were formed.

Environmental Pollutants↗
PubMedDate not supplied

Aromatic hydrocarbon growth from indene.

Aromatic hydrocarbon growth from indene (C9H8), which contains the five-membered ring cyclopentadienyl moiety, was investigated experimentally in a 4 s flow reactor over a temperature range 650-850 degrees C. Major products observed were three C18H12 isomers (chrysene, benz[a]anthracene and benzo[c]phenanthrene), two C17H12 isomers (benzo[a]fluorene and benzo[b]fluorene), and two C10H8 isomers (naphthalene and benzofulvene). Reaction pathways to these products are proposed. Indenyl radical addition to indene produces a resonance-stabilized radical intermediate which further reacts by one of two routes. Rearrangement by intramolecular addition produces a bridged structure that leads to the formation of C17H12 and C10H8 products. Alternatively, beta scission produces biindenyl, which leads to the formation of C18H12 products by a ring condensation mechanism analogous to that proposed for cyclopentadiene-to-naphthalene conversion. Temperature dependencies of both the partitioning between these two routes and the product isomer distributions are consistent with thermochemical modeling using semi-empirical molecular orbital methods. The results further illustrate the role of resonance-stabilized radical rearrangement in aromatic growth and condensation of systems with cyclopentadienyl moieties.

Journal Article↗
PubMed2002

Anaerobic biodegradation of polycyclic aromatic hydrocarbon in soil.

Known concentrations of phenanthrene, pyrene, anthracene, fluorene and acenapthene were added to soil samples to investigate the anaerobic degradation potential of polycyclic aromatic hydrocarbon (PAH). Consortia-treated river sediments taken from known sites of long-term pollution were added as inoculum. Mixtures of soil, consortia, and PAH (individually or combined) were amended with nutrients and batch incubated. High-to-low degradation rates for both soil types were phenanthrene > pyrene > anthracene > fluorene > acenaphthene. Degradation rates were faster in Taida soil than in Guishan soil. Faster individual PAH degradation rates were also observed in cultures containing a mixture of PAH substrates compared to the presence of a single substrate. Optimal incubation conditions were noted as pH 8.0 and 30 degrees C. Degradation was enhanced for PAH by the addition of acetate, lactate, or pyruvate. The addition of municipal sewage or oil refinery sludge to the soil samples stimulated PAH degradation. Biodegradation was also measured under three anaerobic conditions; results show the high-to-low order of biodegradation rates to be sulfate-reducing conditions > methanogenic conditions > nitrate-reducing conditions. The results show that sulfate-reducing bacteria, methanogen, and eubacteria are involved in the PAH degradation; sulfate-reducing bacteria constitute a major component of the PAH-adapted consortia.

Anaerobiosis↗
PubMed2003

PCBs, PCNs, PCDD/Fs, PAHs and Cl-PAHs in air and water particulate samples--patterns and variations.

Methodology for the determination of biologically active polychlorinated biphenyls (PCBs), non-ortho PCBs, polychlorinated naphthalenes (PCNs), polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs), polycyclic aromatic hydrocarbons (PAHs) was used to investigate concentrations and patterns of certain chlorinated PAH (Cl-PAH) in source related samples using synthetic reference mixtures. Thus, in addition to the above mentioned compounds, mono-heptachlorosubstituted fluorenes, phenanthrenes/anthracenes and pyrenes/fluoranthenes (Cl-PAHs) were measured in vapour and particulate air samples from urban road tunnels, samples of settling particulate matter (SPM), and in bottom sediment samples from two point source locations (pulp and paper, and Mg-plant/Fe-Mn-smelter/chlor-alkali) and in the Baltic Sea. Concentrations in air samples followed: PAHs>PCBs>PCNs>non-ortho PCBs or Cl-PAHs>PCDD/Fs. SPM samples collected at increasing distance to the urban area of Stockholm showed: PAHs>PCBs>PCNs>PCDD/Fs>non-ortho PCBs or Cl-PAHs. For all compound groups there was a tenfold (Cl-PAHs fivefold) concentration decrease in SPM samples from highest levels in the urban water area to lowest levels at a distance of 26 km from city centre. PCB profiles of SPM showed similarities with combined profiles of Aroclor 1242 and 1254. PCN profiles of SPM showed similarities with combined profiles of Halowax 1099 and 1014. A correlation with concentration of all tested Cl-PAH and their corresponding parent PAH was found only for Cl-fluorene.

Air↗
PubMed2000

Biodegradation of polycyclic aromatic hydrocarbons by a mixed culture.

We investigated the potential biodegradation of polycyclic aromatic hydrocarbons (PAHs) by an aerobic mixed culture utilizing phenanthrene as its carbon source. Following a 3-5 h post-treatment lag phase, complete degradation of 5 mg/l phenanthrene occurred within 28 h (optimal conditions determined as 30 degrees C and pH 7.0). Phenanthrene degradation was enhanced by the individual addition of yeast extract, acetate, glucose or pyruvate. Results show that the higher the phenanthrene concentration, the slower the degradation rate. While the mixed culture was also capable of efficiently degrading pyrene and acenaphthene, it failed to degrade anthracene and fluorene. In samples containing a mixture of the five PAHs, treatment with the aerobic culture increased degradation rates for fluorene and anthracene and decreased degradation rates for acenaphthene, phenanthrene and pyrene. Finally, it was observed that when nonionic surfactants were present at levels above critical micelle concentrations (CMCs), phenanthrene degradation was completely inhibited by the addition of Brij 30 and Brij 35, and delayed by the addition of Triton X100 and Triton N101.

Acenaphthenes↗
PubMed2003

Supercritical fluid generated stationary phases for liquid chromatography and capillary electrochromatography.

Chromatographic silica-bonded stationary phases have been prepared using supercritical CO(2) as the reaction medium. (29)Si solid-state NMR spectra of the generated bonded silica phases show unreacted silica species Q(3) and Q(4), alongside important resonances for surface-bound ligands, T(1), T(2), and T(3). Initially, a fluorinated octyl silica (C(8)) phase was produced, by reacting (1)H,(1)H,(2)H,(2)H-perfluorooctyltriethoxysilane with silica particles (3 microm) in sc-CO(2) at 60 degrees C and 450 atm for 3 h. In-house-packed LC columns of this fluorinated sc-C(8) silica phase yielded typical reversed-phase behavior when a standard test mix of benzamide (k' = 1.03), benzophenone (k' = 8.11), and biphenyl (k' = 14.92) was eluted. When packed into fused-silica capillaries for CEC, this fluorinated sc-C(8) silica phase gave linear plots of log k' versus percentage MeOH for benzophenone and biphenyl and, in contrast to octyl or octadecyl silica phases, displayed selectivity for aromatic thioureas when chromatographed among a series of synthetic organic thiourea test solutes. Similarily, an octadecyl silica phase (sc-C(18) silica) was prepared by reaction of n-octadecyltriethoxysilane in sc-CO(2), packed at 9500 psi and examined by LC. The sc-C(18) silica LC column yielded high column efficiency (up to 141 000 N/m (fluorene)) and excellent asymmetry factors (1.06, fluorene) without resource to end-capping. Following a second silylating or end-capping step using hexamethyldisilazane in sc-CO(2), sc-end-capped sc-C(18) silica phases elute N,N-DMA before toluene and the toluidine isomers as a single peak, indicating lowered silanol activity according to the Engelhardt test. A rapid separation of the important pharmaceutical substances, ketoprofen, naproxen, fentoprofen, and ibuprofen, on an sc-end-capped sc-C(18) silica phase is also shown.

Journal Article↗
PubMed1985

Covalent binding of a carcinogen as a probe for the dynamics of deoxyribonucleic acid.

In order to determine the kinetic parameters of the binding to DNA of two closely related ultimate carcinogens, 2-(N-acetoxy-N-acetylamino)fluorene (N-Aco-AAF) and 2-(N-hydroxyamino)fluorene (N-OH-AF), three kinds of experiments were performed: measurement of the final amount of adduct (N-Aco-AAF and N-OH-AF), determination of the initial rate, and study of the reaction with deoxyguanosine (N-Aco-AAF only) at temperatures between 4 and 50 degrees C. The kinetic treatment of the chemical equations relies on two main assumptions: (i) binding of carcinogen to the C8 of guanine (G) could occur either with the classical B conformation or with a transient conformational state of the sugar--phosphate chain at the level of the guanine and denoted by G*; (ii) the equilibrium between G and G* is fast as compared to the chemical rate of carcinogen binding. These two assumptions have been verified by comparing experimental and calculated values of some of the data. From experimental data it is possible then to determine the characteristic independent parameters of the reaction: the constant K of the G in equilibrium G* and the enthalpy change delta H of the process, the rate constant k3 of the binding to the C8 of G, and the rate constant k1 of hydrolysis of the carcinogen with their corresponding activation enthalpies E3 and E1. Some essential results obtained are as follows: (a) The amount of G* that represents about 10% of the G at room temperature increases with temperature and is higher in denatured than in native DNA. (b) The values of delta H (approximately 9 kcal mol-1) and delta S (approximately 27 cal K-1 mol-1) of the G in equilibrium G* equilibrium are close to those associated with single base pair opening [Wartell, R.M., & Benight, A.S. (1982) Biopolymers 21, 2069]. (c) N-Aco-AAF reacts only with the G* conformation while N-OH-AF binds preferentially to the "classical" G (B conformation). Therefore, the electrophilic carcinogens behave as probes of the dynamic state of the DNA, but the rate of the G in equilibrium G* exchange is fast as compared to the binding rate of the carcinogen.(ABSTRACT TRUNCATED AT 400 WORDS)

2-Acetylaminofluorene↗
PubMed2003

Biosurfactant- and biodegradation-enhanced partitioning of polycyclic aromatic hydrocarbons from nonaqueous-phase liquids.

A study was conducted on the effect of two different biological factors, microbial surfactants and biodegradation, on the kinetics of partitioning of polycyclic aromatic hydrocarbons (PAHs) from nonaqueous-phase liquids (NAPLs). The effect of rhamnolipid biosurfactants on partitioning into the aqueous phase of naphthalene, fluorene, phenanthrene, and pyrene, initially dissolved in di-2-ethylhexyl phthalate (DEHP) or 2,2,4,4,6,8,8-heptamethylnonane (HMN), was determined in multiple-solute experiments. Biosurfactants at a concentration above the CMC enhanced the partitioning rate of fluorene, phenanthrene, and pyrene but were ineffective with naphthalene. Enhancement of partitioning was also observed in the presence of suspended humic acid-clay complexes, which simulated the solids often present in the subsurface. Biosurfactants sorbed to the complexes modified PAH partitioning between the NAPL and these solids, increasing the fraction of solid-phase PAH. Biodegradation-driven partitioning was estimated in mineralization experiments with phenanthrene initially present in HMN and three representative soil bacterial strains, differing in their potential adherence to the NAPL. In the three cases, the rates of mineralization were very similar and significantly higher than the abiotic rate of partitioning. Our study suggests that in NAPL-polluted sites, partitioning of PAH may be efficiently enhanced by in situ treatments involving the use of biosurfactants and biodegradation.

Biodegradation, Environmental↗
PubMed2006

Molecular simulations of benzene and PAH interactions with soot.

Molecular mechanics simulations and ab initio calculations were performed to investigate the mechanism of PAH-soot adsorption. Partitioning of benzene, naphthalene, fluorene, phenanthrene, anthracene, pyrene, fluoranthene, benzo[a]anthracene, benzo[k]fluoranthene, benzo[a]pyrene, and benzo[g,h,i]perylene between water and soot was modeled with classical and quantum mechanical calculations in order to determine a method for predicting log(K(d)) values. In both cases, the predicted mechanism of adsorption is interaction of the pi-electrons in the PAH and soot (i.e., pi-pi van der Waals forces). Solvation energies, the energy difference between the solute in the gas phase and in the model aqueous phase, calculated with molecular mechanics did not follow the observed solubilities of the PAHs. Molecular dynamics simulations overestimate the favorability of PAHs in the aqueous phase. Hence, the partitioning between the aqueous phase and soot does not accurately correlate with observed log(K(d)) values. Models of PAH adsorption using structures from molecular mechanics and energies from ab initio calculations do produce water-soot partitioning energies that correlate well with observed log(K(d)) values. The log(K(d)) values for benzene, anthracene, fluorene, and benzo[a]pyrene were predicted based on the correlation between calculated partitioning energies and observed log(K(d)) values. Results presented here suggest that partitioning of PAHs onto soot should depend on the size of the PAH, the planarity of PAH molecule, and the aromaticity of the compound. The methodology developed bythis research can be used to predict PAH K(d) values that have not yet been measured.

Benzene↗
PubMed2005

Silver(I) compounds consisting of [2.2]paracyclophane: reversible guest-driven solid-state transformation and incorporation behavior.

Reaction of [2.2]paracyclophane with silver(I) heptafluorobutyrate (AgC3F7CO2) has isolated three novel networks: [Ag4(pcp)(C3F7CO2)4] x pyrene (1), [Ag4(pcp)(C3F7CO2)4] x phen (phen = phenanthrene) (2), and [Ag4(pcp)(C3F7CO2)4] x fluorene (3), and an intercalation compound [Ag4(pcp)(C3F7CO2)4] x 2benzene (4). All the four complexes exhibit two-dimensional (2D) sheet structures in which AgC3F7CO2 form an infinite chain and pcp acts as linkage. 1, 2, and 3 show 2D flat sheets with cavities in which guest molecules are situated, whereas 4 exhibits 2D zigzag layers between which guest benzene molecules are intercalated. Pcp shows mu-di-eta1-eta2 coordination mode in 1, mu-tetra-eta1 coordination mode in 2 and 3, and mu-tetra-eta2 coordination mode in 4. The reversible guest exchanges were observed between complex 1, 2, or 3 and intercalation compound 4. It is unprecedented for metal-organic inclusion complexes that the guest exchange occurs where the guest is the solute molecule. Furthermore, 4 can release the guest, and the original framework was completely recovered after reincorporation of benzene. It should be noted that 4 can incorporate pyrene, phen, and fluorene to give 1, 2, and 3, respectively, after desorption.

Journal Article↗
PubMed1997

Hydrogen Atom Abstraction by Permanganate: Oxidations of Arylalkanes in Organic Solvents.

Oxidations of arylalkanes by (n)()Bu(4)NMnO(4) have been studied in toluene solvent: toluene, ethylbenzene, diphenylmethane, triphenylmethane, 9,10-dihydroanthracene, xanthene, and fluorene. Toluene is oxidized to benzoic acid and a small amount of benzaldehyde; other substrates give oxygenated and/or dehydrogenated products. The manganese product of all of the reactions is colloidal MnO(2). The kinetics of the reactions, monitored by UV/vis spectrometry, show that the initial reactions are first order in the concentrations of both (n)()Bu(4)NMnO(4) and substrate. No induction periods are observed. The same rate constants for toluene oxidation are observed in neat toluene and in o-dichlorobenzene solvent, within experimental errors. The presence of O(2) increases the rate of (n)()Bu(4)NMnO(4) disappearance. The reactions of toluene and dihydroanthracene exhibit primary isotope effects: k(C)()7(H)()8/k(C)()7(D)()8 = 6 (+/-1) at 45 degrees C and k(C)()14(H)()12/k(C)()14(D)()12 = 3.0 (+/-0.6) at 25 degrees C. The rates of oxidation of substituted toluenes show only small substituent effects. In the reactions of dihydroanthracene and fluorene, the MnO(2) product is consumed in a subsequent reaction that appears to form a charge-transfer complex. The rate-limiting step in all of the reactions is hydrogen atom transfer from the substrate to a permanganate oxo group. The enthalpies of activation for the different substrates are directly proportional to the DeltaH degrees for the hydrogen atom transfer step, as is typical of organic radical reactions. The ability of permanganate to abstract a hydrogen atom is explained on the basis of its ability to form an 80 +/- 3 kcal/mol bond to H(*), as calculated from a thermochemical cycle. (This bond strength is slightly lower than given in earlier calculations.) Rates of H(*) abstraction by (n)()Bu(4)NMnO(4) correlate with rates of abstraction by oxygen radicals.

Journal Article↗
PubMed2002

Anionic cyclization of a cross-conjugated enediyne.

Cross-conjugated enediynes cannot follow the Bergman cycloaromatization as it involves a methylenediyne moiety with only five pi e(-), insufficient for aromatization. Under reductive conditions the cyclization is made feasible by generating a product with a Hückel number of pi electrons. We illustrate this principle and demonstrate for the first time an anionic cyclization of a cross-conjugated enediyne that results in formation of a five-membered ring. 9-(3-Phenyl-1-phenylethynylprop-2-ynylidene)-9H-fluorene (3) was reduced by potassium to yield the dianion of 9-(3,4-diphenylcyclopenta-2,4-dienylidene)-9H-fluorene (4(2-)), which contains a cyclopentadienyl fragment, and oxidation with iodine yielded the unstable fulvalene 4.

Alkynes↗
PubMed2002

Ter(9,9-diarylfluorene)s: highly efficient blue emitter with promising electrochemical and thermal stability.

Novel ter(9,9-diarylfluorene)s were synthesized by a Suzuki-coupling reaction of 2-bromofluorene (1) and 2,7-fluorenediboronic ester derivatives (3) with high isolated yields (63-86%). The X-ray structure analysis of ter(9,9'-spirobifluorene) (4aa) revealed that the conjugated chromophore adopts a helical conformation. This conformation effectively releases the steric interaction between the fluorene moieties and prevents inter-chromophore interactions. The introduction of aryl groups at the C9 position of fluorene was highly beneficial to the thermal and morphological stability of these oligomers. These terfluorenes exhibit intense blue fluorescence with excellent quantum yields both in solution ( approximately 100%) and in solid state (66-90%), and possess interesting reversible redox properties. Highly efficient blue light-emitting OLED devices were fabricated using 4aa and 4cc as emitters as well as hole transporters. The devices exhibit low turn-on voltage ( approximately 3 V) and high EL external quantum efficiency (2.5-3%).

Journal Article↗
PubMed2003

Homoleptic cyclometalated iridium complexes with highly efficient red phosphorescence and application to organic light-emitting diode.

Phosphorescence studies of a series of facial homoleptic cyclometalated iridium(III) complexes have been carried out. The complexes studied have the general structure Ir(III)(C-N)(3), where (C-N) is a monoanionic cyclometalating ligand: 2-(5-methylthiophen-2-yl)pyridinato, 2-(thiophen-2-yl)-5-trifluoromethylpyridinato, 2,5-di(thiophen-2-yl)pyridinato, 2,5-di(5-methylthiophen-2-yl)pyridinato, 2-(benzo[b]thiophen-2-yl)pyridinato, 2-(9,9-dimethyl-9H-fluoren-2-yl)pyridinato, 1-phenylisoquinolinato, 1-(thiophen-2-yl)isoquinolinato, or 1-(9,9-dimethyl-9H-fluoren-2-yl)isoquinolinato. Luminescence properties of all the complexes at 298 K in toluene are as follows: quantum yields of phosphorescence Phi(p) = 0.08-0.29, emission peaks lambda(max) = 558-652 nm, and emission lifetimes tau = 0.74-4.7 micros. Bathochromic shifts of the Ir(thpy)(3) family [the complexes with 2-(thiophen-2-yl)pyridine derivatives] are observed by introducing appropriate substituents, e.g., methyl, trifluoromethyl, or thiophen-2-yl. However, Phi(p) of the red emissive complexes (lambda(max) > 600 nm) becomes small, caused by a significant decrease of the radiative rate constant, k(r). In contrast, the complexes with the 1-arylisoquinoline ligands are found to have marked red shifts of lambda(max) and very high Phi(p) (0.19-0.26). These complexes are found to possess dominantly (3)MLCT (metal-to-ligand charge transfer) excited states and have k(r) values approximately 1 order of magnitude larger than those of the Ir(thpy)(3) family. An organic light-emitting diode (OLED) device that uses Ir(1-phenylisoquinolinato)(3) as a phosphorescent dopant produces very high efficiency (external quantum efficiency eta(ex) = 10.3% and power efficiency 8.0 lm/W at 100 cd/m(2)) and pure-red emission with 1931 CIE (Commission Internationale de L'Eclairage) chromaticity coordinates (x = 0.68, y = 0.32).

Journal Article↗
PubMed2006

Molecular wires comprising pi-extended ethynyl- and butadiynyl-2,5-diphenyl-1,3,4-oxadiazole derivatives: synthesis, redox, structural, and optoelectronic properties.

2,5-Diphenyl-1,3,4-oxadiazole (OXD) derivatives with terminal ethynyl- (4a,b) and butadiynyl- (8a,b) substituents have been synthesized in high yields. 2-Methyl-3,5-hexadiyn-2-ol has not been exploited previously in the synthesis of terminal butadiynes. Crystals of 8a and 8b are remarkably stable to long-term storage under ambient conditions. The X-ray crystal structure of 8a reveals that the butadiyne moieties are spatially isolated by the aromatic moieties, which explains the high stability. Two series of derived pi-conjugated molecules, Donor-(C[triple bond]C)(n)-OXD (n = 1, 2) and OXD-(C[triple bond]C)(n)-Donor-(C[triple bond]C)(n)-OXD (n = 1) [Donor = tetrathiafulvalene (TTF), bithiophene, 9-(4,5-dimethyl-1,3-dithiol-2-ylidene)fluorene, and triphenylamine], have been synthesized using Sonogashira reactions and characterized by X-ray crystallography, cyclic voltammetry, and optical absorption/emission spectroscopy. The electron-withdrawing effect of the OXD units is manifested by a positive shift of the donor oxidation waves in these systems: the butadiynylene spacer (n = 2) further shifts the first oxidation waves by 40-80 mV compared to analogues n = 1. The absorption spectra of TTF-OXD hybrids 10d and 11 are blue-shifted by 80 nm compared to the bithienyl-bridged derivative 10f and are similar to the butadiynyl-OXD building-block 8a, demonstrating that conjugation is disrupted by a neutral TTF unit. Solutions of the TTF-OXD and 9-(4,5-dimethyl-1,3-dithiol-2-ylidene)fluorene-OXD hybrids, 10d, 10g, 11, and 13, are only very weakly fluorescent due to quenching from the electron-donor moieties. In contrast, the triphenylamine-OXD hybrids 12a, 12b, 14a, and 14b are fluorescent; the PLQYs of the butadiynylene derivatives 14a and 14b are lower than those of the ethynylene-bridged analogues 12a and 12b.

Journal Article↗
PubMed2006

Triplet energy back transfer in conjugated polymers with pendant phosphorescent iridium complexes.

The nature of Dexter triplet energy transfer between bonded systems of a red phosphorescent iridium complex 13 and a conjugated polymer, polyfluorene, has been investigated in electrophosphorescent organic light-emitting diodes. Red-emitting phosphorescent iridium complexes based on the [Ir(btp)(2)(acac)] fragment (where btp is 2-(2'-benzo[b]thienyl)pyridinato and acac is acetylacetonate) have been attached either directly (spacerless) or through a -(CH(2))(8)- chain (octamethylene-tethered) at the 9-position of a 9-octylfluorene host. The resulting dibromo-functionalized spacerless (8) or octamethylene-tethered (12) fluorene monomers were chain extended by Suzuki polycondensations using the bis(boronate)-terminated fluorene macromonomers 16 in the presence of end-capping chlorobenzene solvent to produce the statistical spacerless (17) and octamethylene-tethered (18) copolymers containing an even dispersion of the pendant phosphorescent fragments. The spacerless monomer 12 adopts a face-to-face conformation with a separation of only 3.6 A between the iridium complex and fluorenyl group, as shown by X-ray analysis of a single crystal, and this facilitates intramolecular triplet energy transfer in the spacerless copolymers 17. The photo- and electroluminescence efficiencies of the octamethylene-tethered copolymers 18 are double those of the spacerless copolymers 17, and this is consistent with suppression of the back transfer of triplets from the red phosphorescent iridium complex to the polyfluorene backbone in 18. The incorporation of a -(CH(2))(8)- chain between the polymer host and phosphorescent guest is thus an important design principle for achieving higher efficiencies in those electrophosphorescent organic light-emitting diodes for which the triplet energy levels of the host and guest are similar.

Journal Article↗
PubMed1986

Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol.

A recently discovered and structurally distinct class of antiepileptic drugs is the (arylalkyl)imidazoles. Two independently discovered representatives of this class, denzimol (alpha-[4-(2-phenylethyl)phenyl]-1H-imidazole-1-ethanol) and nafimidone (2-(1H-imidazol-1-yl)-1-(2-naphthalenyl)ethanone), are undergoing clinical evaluation. Our structure-activity relationship (SAR) studies revealed that in addition to the naphthalenyl and phenethylphenyl aryl moieties of nafimidone and denzimol, respectively, fluorenyl, benzo[b]thienyl, and benzofuranyl aryl groups provided several highly active (arylalkyl)imidazole anticonvulsants. These structurally diverse aryl moieties, and comparable anticonvulsant activities, lend credence to the hypothesis that the pharmacophore of this class of anticonvulsants is the alkylimidazole portion of the molecule, with the lipophilic aryl portion enabling penetration of the blood-brain barrier. We focused our SAR studies on the (fluorenylalkyl)imidazole series. A representative compound from this series is 1-(9H-fluoren-2-yl)-2-(1H-imidazol-1-yl)ethanone. This agent was twice as potent as nafimidone in inhibiting maximal electroshock seizures in mice (po ED50's = 25 and 56 mg/kg, respectively) and considerably less toxic in the rat (po LD50's = 4550 and 504 mg/kg, respectively). The tertiary alcohol alpha-(9H-fluoren-2-yl)-alpha-methyl-1H-imidazole-1-ethanol was as potent as denzimol in mice (po ED50's = 10 and 12 mg/kg, respectively). This series of imidazole anticonvulsants was highly selective; while many compounds displayed potent antielectroshock activity, little or not activity was observed against pentylenetetrazole-induced clonic seizures or in the horizontal screen test for ataxia. All active compounds that we tested in this series, as well as denzimol and nafimidone, potentiated hexobarbital-induced sleeping time in mice, probably by imidazole-mediated inhibition of cytochrome P-450. The SAR's for the anticonvulsant activity and the sleeping time potentiation were similar. The propensity of these (arylalkyl)imidazole anticonvulsants to interact strongly with cytochrome P-450 and thereby impair the metabolism of other antiepileptic drugs may severely limit their clinical utility as anticonvulsants.

Animals↗
PubMed1977

Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. 8. Bis-basic derivatives of carbazole, dibenzofuran, and dibenzothiophene.

A series of bisalkamine esters, bis-basic ethers, and bis-basic ketones of carbazole, N-ethylcarbazole, dibenzofuran, and dibenzothiophene was synthesized and evaluated for antiviral activity. The series also included two bis-basic alkanes of N-ethylcarbazole and one bis-basic carboxamide of dibenzofuran. Structure-activity relationships indicated that within the carbazole and N-ethylcarbazole series the bisalkamine esters gave the most active derivatives while the bis-basic ketone derivatives of dibenzofuran and dibenzothiophene afforded the more potent compounds within the respective series. The [6,5,6]heterocyclic nuclei were compared with the [6,5,6] aromatic nuclei (fluroene and fluoren-9-one) including tilorone with respect to antiviral activity against encephalomyocarditis (EMC) virus. Maximum activity was associated with the bis-basic ketone side chain and fluoren-9-one nucleus.

Animals↗