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At least 19 recordsLinked to original sources
PubMed1975

The metabolism of phenyl o-(2-N-morpholinoethoxy)-phenyl ether hydrochloride in the rabbit and rat.

1. Urinary and faecal excretion of radioactivity in 120 h after oral administration of [U-14-C]phenyl o-(2-N-morpholinoethoxy)phenyl ether hydrochloride (200 mg/kg) were 92 and 3% dose in the rabbit, and 60 and 35% in the rat. 2. Urinary metabolites were produced by aromatic hydroxylation and aryl alkyl ether bond cleavage. Some evidence for formation of dioxomorpholino, oxohydroxymorpholino, and ethanolamino derivatives of the drug was obtained. 3. The aromatic hydroxylation product, p-hydroxyphenyl o-(2-N-morpholinoethoxy)phenyl ether hydrochloride had vasopressor activity comparable with the parent compound, but with shorter duration of action.

Animals↗
PubMed1977

Alopecia induced by inhalation exposure to phenyl glycidyl ether.

Rats and dogs were exposed to heated phenyl glycidyl ether (310 degrees C) vapor at average levels of 1.3, 5.0, and 11.8 ppm (v/v) for 6 hr/day, 5 days/wk, for 90 days. No adverse effects were observed in the dogs and rats other than alopecia in rats at the dose levels of 5.0 and 11.8 ppm. Microscopically, the skin lesions revealed slight acanthosis, hyperkeratosis, and occasional patchy parakeratosis in the epidermis. Follicular keratin plugs were observed with hyperkeratosis of epithelium in the hair follicles and sebaceous glands. Inflammatory reaction was mainly confined to the perifollicular region and affected the hair follicles, resulting in atrophy. The number of hair follicles in the resting stage appeared to increase. The hair shafts revealed impairment of keratinization and fragmentation. Extracted hairs showed an increase in the number of dystrophic follicles and constricted or broken hair shafts.

Alopecia↗
PubMed1979

[Testicular atrophy of mice induced by ethylene glycol mono alkyl ethers (author's transl)].

Toxicities of ethylene glycol (EG) and 6 ethylene glycol mono alkyl ethers administered orally were studied. Mice were given various doses (62.5, 125, 250, 500, 1,000, 2,000 and 4,000 mg/kg body weight) of the compounds daily for 5 days/week, for 5 weeks. High doses of ethylene glycol mono methyl ether (EGM), ethylene glycol mono methyl ether acetate (EGMA), ethylene glycol mono ethyl ether (EGE) and ethylene glycol mono ethyl acetate (EGEA) produced marked testicular atrophy and leucopenia. Dose-responce relation was found in these effects. EGM was more effective than EGE, while ethylene glycol mono butyl ether and ethylene glycol mono phenyl ether had but slight effect and EG had no detectable action on testis and leucocytes. Toxic doses being expressed as mg/kg body weight, esterification seemed to weaken the atrophic action of EGM and EGE, but when expressed as mol/kg, significant difference was found neither between EGM and EGMA nor between EGE and EGEA. The mechanism of testicular atrophy induced by low ethylene glycol mono alkyl ethers is likely to be an inhibitory action on cell division.

Animals↗
PubMed1975

Thin layer chromatographic detection and indirect gas chromatographic determination of three carbamate pesticides.

Carbamate pesticide residues are extracted from vegetables and fruits with methylene chloride. The extracts are spotted on silica gel plates and the pesticides are detected by an enzymatic inhibition technique. For quantitative determination, aliquots of the methylene chloride extracts are evaporated to dryness in a rotary evaporator. After the residues are dissolved in ethanol, 0.5N NaOH is added in the hydrolysis step. To remove a number of possible interferences the hydrolyzed phenols are steam-distilled and treated with 1-fluoro-2,4-dinitrobenzene and/or 4-chloro-alpha,alpha,alpha-trifluoro-3,5-dinitrotoluene to form the ether derivatives. Efficiency in the conversion of the phenolic moieties to the phenyl ethers is about 100%. The resulting electron-capturing derivatives enable the carbamate pesticides to be detected in vegetables and fruits at the 0.05 ppm level. Recoveries of 90-94% were obtained from vegetables and fruits fortified with 0.5-2.0 ppm carbaryl, Mesurol, and propoxur.

Carbamates↗
PubMed1977

Binding specificity of the juvenile hormone carrier protein from the hemolymph of the tobacco hornworm Manduca sexta Johannson (Lepidoptera: Sphingidae).

A series of analogues of insect juvenile hormone (four geometric isomers of methyl epoxyfarnesenate, several para-substituted epoxygeranyl phenyl ethers, and epoxyfarnesol and its acetate and haloacetate derivatives) was prepared to investigate the binding specificity of the hemolymph juvenile hormone binding protein from the tobacco hornworm Manduct sexta. The relative binding affinities were determined by a competition assay against radiolabeled methyl (E,E)-3,11-dimethyl-7-ethyl-cis-10,11-epoxytrideca-2,6-dienoate (JH I). The ratio of dissociation constants was estimated by plotting competitor data according to a linear transformation of the dissociation equations describing competition of two ligands for a binding protein. The importance of the geometry of the sesquiterpene hydrocarbon chain is indicated by the fact that the binding affinity is decreased as Z (cis) double bonds are substituted for E (trans) double bonds in the methyl epoxyfarnesenate series; the unepoxidized analogues do not bind. A carboxylic ester function is important although its orientation can be reversed, as indicated by the good binding of epoxyfarnesyl acetate. In the monoterpene series, methyl epoxygeranoate shows no affinity for the binding protein, but substitution of a phenyl or p-carbomethoxyphenyl ether for the ester function imparts a low, but significant affinity. These data taken together with earlier results indicate that the binding site for juvenile hormone in the hemolymph binding protein is characterized by a sterically defined hydrophobic region with polar sites that recognize the epoxide and the ester functions.

Animals↗
PubMed1975

Gas chromatographic evaluation of the volatile constituents of lung, brain and liver tissues.

Volatile metabolites from rat liver, lung and brain tissues were compared using gas chromatography. Volatiles released from the homogenized tissues at 95-100 degrees C were collected on a poly phenyl ether solid adsorbent. The adsorbed volatiles were examined by high-resolution gas chromatography. Markedly differing overall volatile profiles were observed for the tissue types examined, and it appears that certain constituents may be characteristic of a particular tissue.

Animals↗
PubMed1975

Halogenated hydrocarbons in New Orleans drinking water and blood plasma.

Volatile organics from New Orleans drinking water and pooled plasma were collected on a solid phenyl ether polymer and analyzed by gas chromatographic and mass spectrometric techniques. Thirteen halogenated hydrocarbons were identified in the drinking water. Five halogenated compounds were found in the plasma. Tetrachloroethylene and carbon tetrachloride were found in both the plasma and the drinking water. Considerable variation in the relative concentrations of the halogenated hydrocarbons was noted from day to day in the drinking water.

Adult↗
PubMed1978

[Quantitative determination of the phenolic ester of phenylmalonic acid by an IR spectroscopy method].

A quantitative method was developed for determination of phenyl ether of phenylmalonic acid (I) in the presence of phenol. The method is based on measurement of the optic density of the characteristic absorption bands of I at 1133 and 1770 cm-1 of IR-spectrum. Absorption of I at the above frequencies responded to Ber's law. Determination of I (solution in methylen chloride) was carried out on a standard curve in accordance with equation y : bx for the both frequencies. The value of constants b of the direct regressions for the frequencies of 1133 and 1770 cm-1 were determined with relative errtor of +/- 1.2 and 2.3 per cent respectively. The correlation coefficients were equal to 0.98 and 0.95.

Chromatography, Thin Layer↗
PubMed1975

Chemotherapy of experimental Echinococcus granulosus infection. Trials in CF1 mice and jirds (Meriones unguiculatus).

Mice and jirds with experimental secondary hydatidosis (Echinococus granulous) were treated at various post-infection periods with eight different drugs; iodinized oil of thymol, ethyl-N-dimethyl ether of thymol fumarate, chloroguanide, rifampin, pentamidine isethionate, amphotericin B, suramin, and methotrexate. In initial experiments with methotrexate, mice treated after 99 days of infection had significantly fewer infections at necropsy than did controls (33% and 100%, respecitively). However, in subsequent studies at three dose levels of methotrexate in mice 10 days after infection and in mice and jirds 240 days post infection, no significant differences were found in the percentage of animals infected, cyst size, or number between treated and control animals. The other drugs tested were similarly without effect under the experimental conditions used.

Administration, Oral↗
PubMed1978

Molecular connectivity and substructure analysis.

Antimicrobial and antiviral data sets were analyzed by molecular connectivity. Standard structure--activity relationship equations of high quality were produced in both cases. For phenyl propyl ether activity against Staphylococcus aureus, the three variables 1chi, 3chiP, and 4chiUPC yielded an r of 0.957, significantly better than a pi,sigma analysis. Analysis of benzimidazole antiviral data (Lee strain, B flu virus) revealed that the one variable, 6chiP, yielded an r of 0.950, also better than a reported Hansch analysis. Both data sets were further analyzed by partitioning the important regression variables into terms representing various structural features of the molecules. For the phenyl propyl ethers, the para-region of the phenyl ring is important for improved activity and the negative coefficient on 3chiP corresponds to decreased activity for vic-dihydroxy compounds. For the alkylbenzimidazoles, substitution on the five-membered ring is highly important. No discrimination of six-membered ring positions was revealed. These structure--activity relationship observations can form the basis for synthetic decisions to improve activity.

Antifungal Agents↗
PubMed1978

Synthesis of potential hypolipidemic agents. Reaction of substituted phenyl 2,3-epoxypropyl ethers with adenine, uracil, and thymine.

Three adenine derivatives were found to be active hypolipidemic agents at 10 mg/kg/day. The most active compound was 9-(p-chlorophenoxy-2-hydroxypropyl)adenine (5). Compound 5 significantly lowered serum triglyceride and cholesterol content in male Sprague-Dawley rats and inhibited hepatic phosphatidate phosphohydrolase activity in vitro. The synthesis of these agents involved reacting adenine, uracil, and thymine with a series of substituted phenyl 2,3-epoxypropyl ethers.

Adenine↗
PubMed1975

Repeated topical applications of 1,2,4-trichlorobenzene. Effects on rabbit ears.

In a study to evaluate its acnegenic potential, increasing concentrations of 1,2,4-trichlorobenzene were applied topically to the ventral surface of the rabbit ear three times weekly for 13 weeks. Additional groups of rabbits received similar treatment with petroleum ether (solvent controls), received no treatment (negative controls), and received four once-weekly treatments with hexachlorodiphenyloxide, a known chloracnegenic agent (positive controls). Skin response to 1,2,4-trichlorobenzene was characterized grossly by dermal irritation directly related to the concentration of test material; there were the associated histologic changes of acanthosis and hyperkeratosis; there was no primary follicular involvement characteristic of acneform dermatitis. Dermal responses to hexachlorodiphenyloxide consisted of gross follicular enlargement, with waxy excretion on pressure, and severe scaling. The affected ear appeared thickened up to three times normal size and histologic sections showed primary follicular involvement characterized by marked thickening of the sheath and marked distention of the follicles with keratin, with resultant comedone formation, typical of chloracne.

Acne Vulgaris↗
PubMed1975

The prevention by sulphydryl compounds of the toxicity in the cat of 2,6-dimethoxyphenol and its morpholinopropionyl ester.

1 Intravenous (minus)-2,6-dimethoxyphenyl-2-morpholinopropionate hydrochloride (M&B 16,573) produced anaesthesia of short duration in the mouse, rat, rabbit, cat, dog and monkey. In the cat but not in other species, a severe and usually fatal toxic reaction was seen 1-2 h after administration. 2 This toxic reaction but not the anaesthetic properties of M&B 16,573 was prevented by the intravenous administration of cysteine or N-acetylcysteine. Cysteamine or dimercaprol were ineffective. 3 Intravenous administration of 2,6-dimethoxyphenol or 2,6-dimethoxyquinol in the cat produced a response similar to the delayed toxic effects of M&B 16,573 but not preceded by anaesthesia. The toxic effects of these compounds were prevented by cysteine. 4 Intravenous 4-allyl-2,6-dimethoxyphenyl-2-morpholinopropionate hydrochloride produced anaesthesia in the cat without the delayed toxic effects seen after M&B 16,573. 5 The acute toxicity of 2,6-dimethoxyquinol in mice was reduced by the administration of cysteine or N-acetylcysteine. 6 It is postulated that the delayed effects produced by M&B 16,573 in the cat are due to the formation of 2,6-dimethoxyquinol and 2,6-dimethoxybenzoquinone in this species, the toxicity of the latter being reduced by sulphydryl compounds.

Animals↗
PubMed1977

Quantitative aspects of phenyl substituted alcohol and ether bacteriostatic interaction with Escherichia coli B/5.

It is well established that compounds of the class phenylalkane alcohols and ethers exert their antimicrobial action on the bacterial envelope--probably on the membrane. However, the overall stoichiometry, the number of molecules bound vs those merely added per cell, and the kinds of equilibria involved (site binding vs equipartitioning) are not clear. This work examines antimicrobial action on E. coli B/5 with eight such compounds. Directly determined binding data, plate counting viabilities, radiorespirometry, and microcalorimetry of glucose utilization were evaluated. The compounds mostly bind by simply equipartitioning, up to some threshold level, short of kill. That level depends sharply on the number of alkane carbons in the phenyl alkane derivative, but not on the precise structure. Past the threshold, bacteriostatic action is sudden and complete, probably reflecting cooperative behaviour in the cell envelope. The amount of bound compound at the threshold level is only about 0.5 to 3% of the weight of the bacterial envelope hydrocarbon, when bacteriostasis occurs. There is an unexpectedly small dependence on cell concentration. The principal governors on where the monooxygen phenylalkanes kill cells seems to be merely their concentration or chemical potential, the number of aliphatic carbons, and the binding mechanism. Because of the cell concentration independence, the cells act as if they constituted a second phase, relative to the solution. Results from the microcalorimetric method for assay of bacteriostasis correlate well with those from plate counting or viability assays.

Calorimetry↗