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PubMed1985

The metabolism of muzolimine.

The metabolism of muzolimine, 3-amino-1-(3,4-dichloro-alpha-methyl-benzyl)-2-pyrazoline-5-one has been studied both in vivo and in vitro in various animal species. Using unlabelled muzolimine the major urinary metabolite in all species studied has been shown by chromatography and mass-spectrometry to have properties identical to synthetic N'-(1-aminoethylidene)-3,4-dichloro-acetophenone hydrazone. In addition, 3,4-dichloroacetophenone, 3,4-dichloromandelic and 3,4-dichlorobenzoic acids have been detected and quantified using GLC techniques. In vitro experiments using hepatic microsomal preparations from various species show that cleavage across the C-N1 bond occurs yielding 3,4-dichloroacetophenone and 3-amino-2-pyrazoline-5-one. The hydrazone was the major metabolite produced by these systems. Moreover, this compound also appears as the major metabolite in faecal extracts. Reverse-Phase High-Performance Liquid Chromatographic techniques have been employed for analysis of in vitro metabolism of muzolimine and confirmed the formation of the above metabolites.

Animals↗
PubMed1985

Interaction of cytochrome P-450 with a hydroperoxide derived from butylated hydroxytoluene. Mechanism of isomerization.

Attack of O2 on the phenoxy radical derived from butylated hydroxytoluene resulted in the formation of 2,6-di-t-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadienone (BOOH). This hydroperoxide was rapidly consumed when incubated with rat liver microsomes in the absence of NADPH. The destruction of BOOH was accompanied by formation of the corresponding alcohol (BOH) and a derivative of the alcohol (B(OH)2) in which a t-butyl methyl group was hydroxylated. This diol was produced also when BOH was incubated with microsomes and NADPH, but at a slower rate. Mass spectral analyses of B(OH)2 formed from substrates labeled with either 2H or 18O, showed that oxygen was transferred from the peroxy group to a t-butyl group (via the heme iron of P-450) without migration of the intermediate alcohol from the enzyme active site. The results support a mechanism involving heterolytic O-O bond cleavage during isomerization of the hydroperoxide to B(OH)2. The chiral diol was produced from BOOH nonstereoselectively, but the NADPH/O2-supported hydroxylation of BOH resulted in the formation of a 20% excess of one enantiomer of B(OH)2. Analyses of products formed from the interaction of cumene hydroperoxide with cytochrome P-450 showed that this substrate undergoes rearrangement also; 2-phenyl-1,2-propanediol was produced, together with cumyl alcohol and acetophenone. These results indicate that isomerization competes with other pathways of hydroperoxide destruction by cytochrome P-450.

Animals↗
PubMed1977

[Experimental investigation of psychophysiological effect of a new antidepressant (lofepramine) as compared to imipramine and placebo (author's transl)].

Using 24 non-selected healthy male students the effects of imipramine (single dose of 100 mg orally) and 4'-chloro-2-[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-propyl]-methylamino]-acetophenone-hydrochloride (lofepramine, Gamonil) (single dose of 140 mg orally) in comparison to placebo (doubleblind) on subjective, physiological and performance variables were examined. All subjects (Ss) received the three drugs in a completely counterbalanced sequence. On the basis of their scores on the Depression Scale of the Freiburger Personality Inventory (FPI, Fahrenberg) Ss were divided into two groups of 12 Ss each, "high depression" and "low depression" group. Two-way analyses of variance were computed. Imipramine and Lofepramine elevate scores in the mood scale, but only for the "high depression" group. For the Ss scoring lower in depression no such effect can be demonstrated. The physiological effects are similar. Reported side effects are less for lofepramine than for imipramine.

Antidepressive Agents↗
PubMed1984

Synthesis of further amino-halogen-substituted phenyl-aminoethanols.

Starting from clenbuterol as a lead structure, new 4-amino-phenyl-aminoethanol analogues have been synthesized by different approaches. In these compounds one or both of the chlorine atoms of clenbuterol are replaced by other residues. This has led to compounds with high intrinsic beta 2-mimetic and/or beta 1-blocking activities. 1-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-2-tert.-butylamino-ethanol hydrochloride (mabuterol) has been selected for clinical development. A detailed description is given also of the syntheses of intermediary new acetophenone derivatives as well as of the resolution of mabuterol into its enantiomers.

Adrenergic beta-Agonists↗
PubMed1983

[Synthesis and antibacterial activity of perchlorylchloramphenicol].

Starting from p-perchloryl acetophenone we have synthesized the perchloryl analogue of chloramphenicol. The new compound is the first chloramphenicol analogue possessing a higher antimicrobial activity as chloramphenicol itself. It showed an about twofold activity against 18 different microbes in the hole plate diffusion test, compared with the parent compound.

Anti-Bacterial Agents↗
PubMed1983

[Experimental observations on the iodination of phenols in the preparation of intermediates of pharmaceutical interest].

A study has been made on the iodination of phenols by elemental iodine in Na2CO3 solution. The results attained by applying the suggested procedure to a number of practical cases have been very encouraging. This method gives rise to the iodine derivatives of aldehydes (2-hydroxy- and 4-hydroxy-3,5-diiodobenzaldehyd), ketones (2-hydroxy-5-iodo-, 2-hydroxy-3,5-diiodo- and 4-hydroxy-3,5-diiodo-acetophenone, 4-hydroxy-3,5-diiodo-propiophenone), acids (3,5-diiodo-4-hydroxybenzoic acid, 3-formyl-4-hydroxy-5-iodobenzoic acid), aminoacids (3-iodo- and 3,5-diiodo-tyrosine), esters (methyl ester of 2-hydroxy- and 4-hydroxy-3,5-diiodobenzoic acid, methyl ester of 3-iodo-5-chloro-, 3-iodo-5-bromo- and 3,4,5-triiodosalicylic acid, dimethyl- and diethyl-ester of 4-hydroxy-5-iodo-isophthalic acid), amides (2-hydroxy-3,5-diiodobenzamide) and benzoxazole derivatives (2-(2'-hydroxy-3',5'-diiodophenyl)benzoxazole).

Chemical Phenomena↗
PubMed1982

Oxiconazole, a new imidazole derivative. Evaluation of antifungal activity in vitro and in vivo.

The new imidazole derivative Z-[2,4-dichloro-2-imidazol-1-yl)acetophenone]-O-(2,4-dichlorobenzyl)-oxime nitrate (oxiconazole, Ro 13-8996) is characterized by a broad fungistatic spectrum against the agents of human mycoses in vitro. In addition, fungicidal activity of various degree was found in selected species (Aspergillus fumigatus, Cryptococcus neoformans, Candida albicans and Trichophyton mentagrophytes). Synthesis of DNA was inhibited by subinhibitory concentrations of oxiconazole in parallel to cell multiplication, whereas synthesis of RNA, protein and carbohydrate was decreased to a lesser extent. The most relevant findings was high topical activity in both trichophytosis in the guinea-pig and vaginal candidiasis in the rat. In these 2 models, oxiconazole proved to be more potent than several reference compounds from the group of imidazole antimycotics. Systemic oral activity of oxiconazole was also found in three mouse models, namely in dermal infection with T. mentagrophytes var. quinckeanum, systemic histoplasmosis and, just to a low degree, systemic candidiasis, but the compound proved to be inactive in cryptococcosis and aspergillosis in the mouse. Based on our findings, a clinical evaluation of oxiconazole as a topical antimycotic in human superficial mycosis, seems to be justified.

Animals↗
PubMed1978

Thermal degradation products of homopolymer polystyrene in air.

Polystyrene without additional compounds was treated in a laboratory oven at elevated temperatures (200 degrees, 350 degrees, 500 degrees C) under slight air flow (0.7 l/min). The thermal degradation products appearing in different phases (gases, vapors, aerosols) were collected and analyzed by methods of chromatography. Thermogravimetric analysis showed the thermal degradation of the polymer to begin at 270 degrees C in air and stop at 425 degrees C. The main groups of vaporized compounds generated were monoalkyl-substituted aromatic hydrocarbons and their oxidized products, of which styrene monomer and benzaldehyde were the most abundant. Only trace amounts of carbon monoxide and aliphatic compounds (hydrocarbons, aldehydes, and acids) were produced. The aerosol produced, the amount of which increased as the temperature rose, contained mainly fragments of the polymer chain (e.g., dimers and trimers of styrene). The traces of styrene, cumene, and ethylbenzene that appeared at 200 degrees could represent residual compounds in the initial polymer and indicate the beginning of the thermal degradation. If proportional concentrations are kept as a criterion, the important products, from the point of view of industrial hygiene, were styrene, benzaldehyde, styrene oxide, acetophenone, and l-phenylethanol. The large amount of aerosol that appeared may also be of practical importance.

Acids↗
PubMed1994

Halogenated isoniazid derivatives as possible antimycobacterial and anti-HIV agents--III.

As part of a research directed to the synthesis of novel isoniazid derivatives with potential activity on mycobacteria and HIV virus, the acetophenone-isonicotinoylhydrazones 3 and the 4-aryl-1-methoxy-1-(4-pyridyl)- 2,3-diaza-1,3-butadienes 5, obtained by reaction between isonicotinoylhydrazones and diazomethane, have been prepared and tested for such activities. Both classes of derivatives showed interesting growth inhibitory activity on non-tubercular mycobacteria, including the emerging M. avium. Such activity appears to be linked to fluorine and/or chlorine presence on benzene rings. In contrast, none of the compounds submitted to the anti-AIDS in vitro screening, displayed any protection against HIV-1 virus-induced cytopathic effect in T4-lymphocyte cell lines.

Antiviral Agents↗
PubMed1993

[The degradation mechanism of penequine hydrochloride in aqueous solutions].

Penequine hydrochloride (I) is a new potent anticholinergic drug, the degradation mechanism of I in aqueous solutions is reported in this paper. I is an ethereal compound, stable in neutral and alkaline solutions, but it decomposes in strong acidic solutions. Its main degradation products have been separated and identified by means of TLC, MS, GC/MS and GC/FTIR. With reference to the general degradation rule of ethereal compound and the structure of the degradation products, we deduced that the ether linkage of I splits in acidic solutions by the catalysis of hydrogen ion, producing 3-quinuclidinol (DP1) and 1-phenyl-1-cyclopentyl glycol. The latter turns into 1-phenyl-1-cyclopentyl acetaldehyde through dehydration and rearrangement. In addition, small amounts of other degradation compounds, e. g. benzaldehyde, acetophenone, phenylcyciopentyl ketone, etc. have also been found, but the mechanism remains to be further studied.

Cyclopentanes↗
PubMedDate not supplied

Physiological disposition and metabolic fate of a new antiarrhythmic agent, alpha, alpha-dimethyl-4-(alpha, alpha, beta, beta-tetrafluorophenethyl) benzylamine in the rat, dog, monkey, baboon, and man.

The physiological disposition of a new orally active antiarrhythmic drug, alpha, alpha-dimethyl-4-(alpha, alpha, beta, beta-tetrafluorophenethyl)benzylamine (MK-251) was investigated in the rat, dog, rhesus monkey, baboon, and man. MK-251 was extensively absorbed after oral administration in all species. Fecal excretion was the major route of tracer elimination in the rat (70%) and dog (80%), whereas the monkey, baboon, and man excreted the majority of the dose via the urine (40-80%). MK-251 and/or its metabolites were widely distributed in rat tissues and exhibited tissue/plasma ratios greater than one in most instances. The lung, liver, and kidney possessed a high tissue affinity for drug and metabolites. The plasma and urinary profile of radioactivity indicated extensive metabolism of MK-251 in all species. Less than 5% of the plasma and urinary radioactivity was identified as unchanged drug. In spite of extensive metabolic transformations, a remarkable feature of this drug is its persistence in the plasma for long periods of time. This is thought to be due to tissue affinity. The metabolic pattern for MK-251 was essentially the same in all species. The major metabolites present in the plasma and the urine were identified as the carbinol analog of MK-251, 2-[4-(alpha, alpha, beta, beta-tetrafluorophenethyl)phenyl]-2-propanol (I), and its glucuronide conjugate. Other metabolites characterized in the urine and plasma were: the N-glucuronide of MK-251, 2-[4-(alpha, alpha, beta, beta-tetrafluorophenethyl)phenyl]propene (II), 2-nitro-2-[4-(alpha, alpha, beta, beta-tetrafluorophenethyl)phenyl]propane (III), alpha, alpha-dimethyl-4-(alpha, alpha, beta, beta-tetrafluorophenethyl)benzyl methyl ether (IV-1) and 4-(alpha, alpha, beta, beta-tetrafluorophenethyl), acetophenone (IV-2). Two minor urinary metabolites were tentatively identified as the N-hydroxy analog of MK-251 and the glycol analog of carbinol I. The in vivo formation of the methyl ether represents the first report of alkylation of a tertiary alcohol.

Adult↗
PubMed1996

Metabolism of all-trans, 9-cis, and 13-cis isomers of retinal by purified isozymes of microsomal cytochrome P450 and mechanism-based inhibition of retinoid oxidation by citral.

The involvement of a series of microsomal cytochrome P450 (P450) isozymes in all-trans-retinoid metabolism, including the conversion of all-trans-retinal to all-trans-retinoic acid, was previously described. In the current study, we examined the role of seven liver microsomal P450 isozymes in the oxidation of three isomers of retinal. P450 1A1, which was not tested previously, is by far the most active in the conversion of all-trans-, 9-cis-, and 13-cis-retinal to the corresponding acids, as well as in the 4-hydroxylation of all-trans- and 13-cis retinal. In contrast, P450s 2B4 and 2C3 are the most active in the 4-hydroxylation of 9-cis-retinal, with turnover numbers approximately 7 times as great as that of P450 1A1. The inclusion of cytochrome b5 in the reconstituted enzyme system is without effect or inhibitory in most cases but stimulates the 4-hydroxylation of 9-cis-retinal by P450 2B4, giving a turnover of 3.7 nmol of product/min/nmol of this isozyme, the highest for any of the retinoid conversions we have studied. Evidence was obtained for two additional catalytic reactions not previously attributed to P450 oxygenases: the oxidation of all-trans- and 9-cis-retinal to the corresponding 4-oxo derivatives by isoform 1A2, and the oxidative cleavage of the acetyl ester of vitamin A (retinyl acetate) to all-trans-retinal, also by isoform 1A2. The physiological significance of the latter reaction, with a Km for the ester of 32 microM and a Vmax of 18 pmol/min/nmol of P450, remains to be established. We also examined the effect on P450 of citral, a terpenoid alpha, beta-unsaturated aldehyde and a known inhibitor of cytosolic retinoid dehydrogenases. Evidence was obtained that citral is an effective mechanism-based inactivator of isozyme 2B4, with a KI of 44 microM as determined by the oxidation of 1-phenylethanol to acetophenone, and by isozyme 1A2 in the oxidation of all-trans-retinal to the corresponding acid and by isozyme 2B4 in the 4-hydroxylation of all-trans-retinol and retinoic acid. Thus, citral is not suitable for use in attempts to distinguish between retinoid conversions catalyzed by dehydrogenases in the cytoplasm and by P450 cytochromes in the endoplasmic reticulum.

Acyclic Monoterpenes↗
PubMed1996

Synthesis of some novel pyrazoline and cyanopyridine derivatives as antimicrobial agents.

Substituted chalcones 2a-j prepared by the treatment of 4'(p-chlorophenylsulphonamido)acetophenone 1 with araldehydes, on condensation with hydrazine hydrate in ethanol and acetic acid provided the desired pyrazolines of the type 3a-j and 4a-j. The same chalcones 2a-j made to react with malononitrile in the presence of ammonium acetate yielded cyanopyridines 5a-j. The structure was confirmed by elemental analyses, IR, NMR and MS spectral studies. The pharmacological profile of the compounds synthesised is described. Most of the compounds displayed their maximum activity against E. coli. Compounds 2b, 2d, 5b, 5d, 5e, 5h and 5i have been selected for their agrochemical screening by DuPont Agricultural Products, U.S.A.

Anti-Bacterial Agents↗
PubMed1996

Halogenated isoniazid derivatives VI. Evaluation of anti-HSV-1 and anti-HIV-1 in vitro activities of fluorinated analogues.

The synthesis and evaluation of antiviral in vitro activity are reported of some 2'-(1-arylethyl)isonicotinohydrazides (5a-d) and N-(1-arylethyl)isonicotinohydrazonic acids (6a-d), obtained by reducing fluorinated acetophenone isonicotinoylhydrazones (2a-d) with sodium cyanoborohydride. These INH analogues, along with other ones previously prepared, i.e. benzaldehyde isonicotinoylhydrazones 1, 4-aryl-1-methoxyl-1-(4-pyridyl)-2,3-diaza-1,3-butadienes 3 and 5-aryl-4-methyl-2-(4-pyridyl)-delta 2-1,3,4-oxadiazolines 4, were assayed for anti-HSV-1 activity on the monoblastoid cell line U937. Only some compounds (1b, 1d, 4d and 4e) displayed a moderate antiherpetic activity. In addition, the reduced compounds 5 and 6, submitted to the anti-HIV-1 screening, did not display significant effects in reducing virus-induced cytopathogenicity. The cytotoxicity of all compounds has been assayed on Vero cells and some considerations in correlation with structure are discussed.

Animals↗
PubMed1997

Synthesis and antimicrobial activities of 2-[(alpha-methylbenzylidene)-hydrazino]benzoxazoles.

New 2-[(alpha-methylbenzylidene)hydrazino]benzoxazole derivatives have been synthesized by reacting ortho or para substituted acetophenones with 2-hydrazinobenzoxazole in ethanol. The structures of the synthesized compounds were confirmed by microanalysis, IR and NMR spectral data. Antimicrobial activities of the compounds were investigated by the microdilution susceptibility test in Mueller-Hinton broth and Sabouraud liquid medium. Test organisms: Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 as Gram (+) bacteria, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa, ATCC 27853 as Gram (-) bacteria, and Candida albicans, Candida stellatoidea, Candida parapsilosis and Candida pseudotropicalis as yeasts. Among the compounds tested 2-[(alpha-methyl-4-chlorobenzylidene)hydrazino]benzoxazole (compounds 4) and 2-[(alpha-methyl-4-nitrobenzylidene)hydrazino]benzoxazole (compound 8) showed the most favorable activity.

Anti-Bacterial Agents↗
PubMed1997

Application of gas-liquid chromatography to the analysis of essential oils. Part XVII. Fingerprinting of essential oils by temperature-programmed gas-liquid chromatography using capillary columns with non-polar stationary phases. Analytical methods committee.

Problems in obtaining reproducible results when 'fingerprinting' essential oils by temperature-programmed gas-liquid chromatography have been reported on in Parts VII and VIII of this series. Those reports were concerned with the general problems and the use of packed columns. This report is concerned with the use of capillary columns and non-polar stationary phases. A collaborative study using capillary columns with non-polar stationary phases has resulted in a method which specifies the 'g-pack value' of a column and gives reproducible relative retention indices for the test compounds limonene, acetophenone, linalol, naphthalene, linalyl acetate and cinnamyl alcohol. The method has been applied successfully to the examination of oil of rosemary. A recommended method is given for the reproducible temperature-programmed gas-liquid chromatographic fingerprinting of essential oils using capillary columns with non-polar stationary phases.

Chromatography, Gas↗
PubMed1998

Odorant response properties of convergent olfactory receptor neurons.

Information about odorant stimuli is thought to be represented in spatial and temporal patterns of activity across neurons in the olfactory epithelium and the olfactory bulb (OB). Previous studies suggest that olfactory receptor neurons (ORNs) distributed in the nasal cavity project to localized regions in the glomerular layer of the OB. However, the functional significance of this convergence is not yet known, and in no studies have the odorant response properties of individual ORNs projecting to defined OB regions been measured directly. We have retrogradely labeled mouse ORNs connecting to different glomeruli in the dorsal OB and tested single cells for responses to odorants using fura-2 calcium imaging. ORNs that project to clusters of dorsomedial (DM) glomeruli exhibit different odorant response profiles from those that project to dorsolateral (DL) glomeruli. DL-projecting ORNs showed responses to compounds with widely different structures, including carvone, eugenol, cinnamaldehyde, and acetophenone. In contrast, DM-projecting neurons exhibited responses to a more structurally restricted set of compounds and responded preferentially to organic acids. These data demonstrate that ORN afferents segregate by odorant responsiveness and that the homogeneity of ORN and glomerular input varies with different OB regions. The data also demonstrate that a subpopulation of ORNs projecting to DM glomeruli is functionally similar.

Animals↗