Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Heptanes”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 19 recordsLinked to original sources
PubMed1992

Fluoronaphthyridines as antibacterial agents. 6. Synthesis and structure-activity relationships of new chiral 7-(1-, 3-, 4-, and 6-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)naphthyridine analogues of 7-[(1R,4R)-2,5- diazabicyclo[2.2.1]heptan-2-yl]-1-(1,1-dimethylethyl)-6-fluoro-1,4-dihy dro-4-oxo-1,8-naphthyridine-3-carboxylic acid. Influence of the configuration on blood pressure in dogs. A quinolone-class effect.

A series of novel chiral 7-(1-, 3-, 4-, and 6-methyl-[(1R,4R)-2,5- diazabicyclo[2.2.1]heptan-2-yl]-substituted naphthyridines has been prepared with the aim of obtaining good in vitro and in vivo antibacterial agents with a decrease of the pseudoallergic type reaction when compared to that observed with 7[(1R,4R)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(1,1-dimethylethyl )1,4- dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid (1a) (BMY 40062). The derivatives 7-[(1R,4R,6S)-6-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]- 1-(1,1-dimethylethyl)-6-fluro-1,4-dihydro-4-oxo-1,8-naphthyridine- 3-carboxylic acid (41) and 7-[(1R,4R,6S)-6-methyl-2,5-diazabicyclo[2.2.1]heptan-2- yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxy lic acid (49) showed potent in vitro and in vivo antibacterial activity against Gram-positive and Gram-negative bacteria. The derivative 49 displayed a less marked decrease in blood pressure (MAP), compared to that of 1a, after intravenous infusion in dogs and was selected as a potential candidate for preclinical trials.

Animals↗
PubMed1982

Synthesis of prostanoids with bicyclo[2.2.1]heptane, bicyclo[3.1.1]heptane, and bicyclo[2.2.2]octane ring systems. Activities of 15-hydroxy epimers on human platelets.

A number of prostanoids with bicyclo[2.2.1]heptane, bicyclo[3.1.1]heptane, and bicyclo[2.2.2]octane ring systems have been prepared by routes which allow the introduction of the omega chain after the alpha chain. The introduction of a 16-p-halophenoxy substituent confers platelet aggregation activity on both 15 alpha- and 15 beta-hydroxy epimers. In the case of the pinane thromboxane ring system, the natural omega-chain compound is an inhibitor of aggregation, whereas the 16-p-fluorophenoxy analogue is a potent aggregation agent.

Bridged Bicyclo Compounds↗
PubMed2001

Separation of 6-deoxy-heptan [correction of 6-deoxy-heptane] from a smooth-type lipopolysaccharide preparation of Burkholderia pseudomallei.

Smooth-type lipopolysaccharide (LPS) of Burkholderia pseudomallei has been reported to contain two kinds of O-antigenic polysaccharides, a 1,3-linked homopolymer of 6-deoxy-heptose and a polymer with a repeating unit of -->3)-glucose-(1-->3)-6-deoxy-talose-(1--> with O-acetyl or O-methyl modifications. A LPS preparation containing these two polysaccharides was separated by gel-permeation chromatography in this study. Chemical analysis of the separated fractions revealed the 6-deoxy-heptan [corrected] to be a polysaccharide without a lipid portion and the polymer of glucose and 6-deoxy-talose to be an O-antigenic polysaccharide of the LPS. This result was further supported by the assay of these polysaccharide molecules for macrophage activation activity. The 6-deoxy-heptan [corrected] showed no macrophage activation, indicating that this polysaccharide was not the LPS, but one of the capsular polysaccharides of B. pseudomallei.

Animals↗
PubMed1996

Evidence for an Elongation/Reduction/C1-Elimination Pathway in the Biosynthesis of n-Heptane in Xylem of Jeffrey Pine.

The biosynthetic pathway to n-heptane was investigated by examining the effect of the [beta]-keto acyl-acyl carrier protein synthase inhibitor (2R,3S)-2,3-epoxy-4-oxo-7E,10E-dodecadienamide (cerulenin), a thiol reagent ([beta]-mercaptoethanol), and an aldehydetrapping reagent (hydroxylamine) on the biosynthesis of n-[14C]heptane and putative intermediates in xylem sections of Jeffrey pine (Pinus jeffreyi Grev.& Balf.) incubated with [14C]acetate. Cerulenin inhibited C18 fatty acid biosynthesis but had relatively little effect on radiolabel incorporation into C8 fatty acyl groups and n-heptane. [beta]-Mercaptoethanol inhibited n-heptane biosynthesis, with a corresponding accumulation of radiolabel into both octanal and 1-octanol, whereas hydroxylamine inhibited both n-heptane and 1-octanol biosynthesis, with radiolabel accumulation in octyl oximes. [14C]Octanal was converted to both n-heptane and 1-octanol when incubated with xylem sections, whereas [14C]1-octanol was converted to octanal and n-heptane in a hydroxylamine-sensitive reaction. These results suggest a pathway for the biosynthesis of n-heptane whereby acetate is polymerized via a typical fatty acid synthase reaction sequence to yield a C8 thioester, which subsequently undergoes a two-electron reduction to generate a free thiol and octanal, the latter of which alternately undergoes an additional, reversible reduction to form 1-octanol or loss of C1 to generate n-heptane.

Journal Article↗
PubMed1986

Identification of the n-heptane metabolites in rat and human urine.

Numerous n-heptane metabolites have been identified and quantified by gas chromatography and mass spectrometry in some tissues and in the urine of Sprague Dawley rats exposed for 6 h to 1800 ppm n-heptane. 2-Heptanol and 3-heptanol were the main biotransformation products of the solvent. 2-Heptanone, 3-heptanone, 4-heptanol, 2,5-heptanedione, gamma-valerolactone, 2-ethyl-5-methyl-2,3-dihydrofuran and 2,6-dimethyl-2,5-dihydropyran were also found as metabolites of n-heptane. In five shoe factory workers and in three rubber factory workers the mean exposure to technical heptane was measured (n-heptane ranged between 5 and 196 mg/m3). In the urine collected at the end of their work shift some n-heptane biotransformation products were found: 2-heptanol, 3-heptanol, 2-heptanone, 4-heptanone and 2,5-heptanedione. 2-Heptanol was the main n-heptane metabolite and its urinary concentrations ranged between 0.1 and 1.9 mg/l. Urinary 2,5-heptanedione was detectable only in some samples and at very low concentration (0.1-0.4 mg/l). These data suggest that n-heptane can be considered as a neurotoxic product, since it gives rise to 2,5-heptanedione, but the small amount of the urinary metabolite is very unlikely to cause clinical damage to the peripheral nervous system.

Animals↗
PubMed2004

Development of headspace solid-phase microextraction with on-fiber derivatization for determination of hexanal and heptanal in human blood.

Hexanal and heptanal in human blood have been regarded as potential biomarkers of lung cancer. Owing to their high volatilities and activities, it is difficult to accurately measure the two biomarkers. In the current work, headspace solid-phase microextraction (HS-SPME) with on-fiber derivatization technique was developed for quantitative analysis of hexanal and heptanal in human blood. In the proposed method, the two aldehydes in blood were headspace extracted by using a poly (dimethylsiloxane)/divinylbenzene (PDMS/DVB) fiber with O-2,3,4,5,6-(pentafluorobenzyl) hydroxylamine (PFBHA) at 60 degrees C for 8 min. The aldehyde oximes formed on the fiber were desorbed and analyzed by gas chromatography-mass spectrometry (GC-MS). The method validations including detection limit, recovery and precision were studied. It was found that the method provided low detection limits of 0.006 nM for hexanal and 0.005 nM for heptanal, recoveries from 89% to 95% and R.S.D. values less than 8.5%. The present method was applied to quantitative analysis of hexanal and heptanal in normal blood and lung cancer blood. Hexanal concentrations from 7.33 to 15.23 microM and heptanal concentrations from 2.47 to 9.23 microM were found in the lung cancer blood, while both hexanal and heptanal in the control blood were lower than 0.6 microM. This further demonstrated that hexanal and heptanal might be the biomarkers of lung cancer. The experimental results showed that GC-MS and HS-SPME with on-fiber derivatization is a simple, rapid, sensitive and solvent-free method for determination of in hexanal and heptanal human blood.

Aldehydes↗
PubMed2004

Molecular dynamics simulation of the coalescence of nanometer-sized water droplets in n-heptane.

Molecular dynamics simulations using a modified Drieding 2.21 force field were carried out to study the coalescence behavior of nanometer-sized water droplets in vacuum and in n-heptane. The coalescence mechanisms of the water droplets in the above-noted environments are fairly similar in a sense that the water droplets form a bridge linking the droplets before they merge. However, in the latter situation, due to the presence of n-heptane molecules in between the water droplets, the coalescence was observed to be slowed down considerably, especially in the first 10 ps of the process. However, once the bridge is formed, the water droplets, in both situations, spend about the same amount of time to form a single droplet. The maximum distance between the droplets above which coalescence does not occur was found to be 10 A. In terms of the dynamics, the diffusion coefficient of n-heptane in the emulsion system was very close to its value in the pure liquid form. This may be because n-heptane is the continuous phase. Nonetheless, the dynamic behavior of water in n-heptane is different from that of pure water during and after the coalescence. In particular, the self-diffusion coefficient of water molecules in n-heptane is about 20% higher than the experimental value of pure water. Due to the lack of strong attraction forces between water and n-heptane molecules, the n-heptane molecules were observed to orient themselves perpendicularly to the water/n-heptane interfaces so that the contacting area is minimized.

Journal Article↗
PubMed2003

An evaluation of amide group planarity in 7-azabicyclo[2.2.1]heptane amides. Low amide bond rotation barrier in solution.

Here we show that amides of bicyclic 7-azabicyclo[2.2.1]heptane are intrinsically nitrogen-pyramidal. Single-crystal X-ray diffraction structures of some relevant bicyclic amides, including the prototype N-benzoyl-7-azabicyclo[2.2.1]heptane, exhibited nitrogen-pyramidalization in the solid state. We evaluated the rotational barriers about the amide bonds of various N-benzoyl-7-azabicyclo[2.2.1]heptanes in solution. The observed reduction of the rotational barriers of the bicyclic amides, as compared with those of the monocyclic pyrrolidine amides, is consistent with a nitrogen-pyramidal structure of 7-azabicyclo[2.2.1]heptane amides in solution. A good correlation was found between the magnitudes of the rotational barrier of N-benzoyl-7-azabicyclo[2.2.1]heptanes bearing para-substituents on the benzoyl group and the Hammett's sigma(p)(+) constants, and this is consistent with the similarity of the solution structures. Calculations with the density functional theory reproduced the nitrogen-pyramidal structures of these bicyclic amides as energy minima. The calculated magnitudes of electron delocalization from the nitrogen nonbonding n(N) orbital to the carbonyl pi orbital of the amide group evaluated by application of the bond model theory correlated well with the rotational barriers of a variety of amides, including amides of 7-azabicyclo[2.2.1]heptane. The nonplanarity of the amide nitrogen of 7-azabicyclo[2.2.1]heptanes would be derived from nitrogen-pyramidalization due to the CNC angle strain and twisting of the amide bond due to the allylic strain.

Journal Article↗
PubMed1984

Identification of volatile metabolites of inhaled n-heptane in rat urine.

Alkanes, alcohols, and ketones which are metabolized to a gamma-diketone can produce peripheral neuropathy in experimental animals and in man. A study was conducted to obtain information about the metabolic pathway of n-heptane and its potential neurotoxicity. Female Wistar rats were exposed to 2000 ppm n-heptane inhalation for 12 weeks. Metabolites in urine were identified by gas chromatography-mass spectrometry. Urinary metabolites were quantified following 6-hr n-heptane exposures. n-Heptane metabolites were 1-, 2-, 3-, and 4-heptanols, 2- and 3-heptanones, 2,5- and 2,6-heptanediols, 5-hydroxy-2-heptanone, 6-hydroxy-2-heptanone, 6-hydroxy-3-heptanone, 2,5- and 2,6-heptanediones, and gamma-valerolactone. The amount of urinary metabolites increased greatly after the second exposure day, achieving a steady-state concentration on subsequent exposure days over the 12 weeks of the exposure regimen. These results showed that n-heptane was metabolized mainly by hydroxylation at omega- 1 carbon atom and to a lesser extent at the omega- 2 carbon atom. 2-Heptanol, 6-hydroxy-2-heptanone, and 3-heptanol were the major metabolites and were excreted as sulfates and glucuronides. 2,5-Heptanedione, which is a neurotoxic agent, was the metabolite found in least amounts (2.4 +/- 2 micrograms/rat) in the urine. No clinical evidence of neurotoxicity was observed after n-heptane exposure. Apparently, the lack of neurotoxicity was due to a low production of 2,5-heptanedione, the toxic metabolite.

Animals↗
PubMed1993

Calibration of albumin-fatty acid binding constants measured by heptane-water partition.

Most measurements of binding affinity of albumin for long-chain fatty acids are based on heptane-water partition. In this method, equilibrium partition of fatty acid between heptane and an albumin-containing buffer is calibrated using the partition ratio between heptane and buffer in the absence of protein. In the current study, we used a variety of techniques to examine potential problems with this approach. Hydrophobic impurities in commercial [3H]palmitate preparations were incompletely removed by standard purification techniques. These impurities contributed from 5% of the total radioactivity in the heptane phase at low albumin concentrations (5 microM) to 62% at higher albumin concentrations (500 microM), thus confounding determination of binding affinity. These were identified by gas chromatography/mass spectroscopy as radio-labeled glycerol monopalmitate and monostearate. When albumin was not present, the partition ratio was similar to values reported by others. However, our results varied by a factor of four (265-1,119) depending on how the solutions were prepared. Although a true equilibrium partition must not depend on starting conditions, the partition ratio after 24-72 h was > 2x as large when tracer [3H]palmitate was added to the heptane phase than when it was added to the aqueous phase. Results also depended on the relative volumes of heptane and buffer used, approaching a maximum of 1,445 +/- 112 for very low heptane/buffer volume ratios. Much of this variability was due to hydrophilic impurities in [3H]palmitate, which ranged from 0.2 to 1.2% in commercial lots down to 0.1-0.5% after alkaline ethanol extraction and < 0.05% after thin-layer chromatography (TLC).(ABSTRACT TRUNCATED AT 250 WORDS)

Calibration↗
PubMed1990

[Spectral interactions of cytochrome P-450 with n-heptane and methanol].

Methanol interacts with cytochrome P-450 to produce the reversed type I spectral change. In the presence of type I substrate n-heptane, the methanol induced spectrum disappears without detectable effects of interaction suggesting that methanol is a very weak ligand for heme iron of cytochrome P-450. Methanol strongly lowers the apparent spectral dissociation constant (Ks app) of n-heptane binding with rat liver cytochrome P-450 both in control and C6-C9 petroleum fraction inhaled group. In control group, titration of cytochrome P-450 with methanolic solutions of n-heptane does not change the maximal spectral interaction (Amax) observed with pure n-heptane. However in the inhaled group during titration of induced cytochrome P-450 with methanolic solutions of n-heptane an additional type I spectral change is observed. Thus addition of "equivalent" amounts of methanol into the reference cuvette during titration with methanolic solutions overestimates the true magnitude of type I spectral change of cytochrome P-450 with n-heptane.

Animals↗
PubMed1998

Use of Fourier transform infrared (FTIR) spectroscopy to follow the adsorption of heptane and 1,4-dioxane vapors on a zinc oxide surface.

Vapor adsorption isotherms of two nonpolar model compounds, heptane and 1,4-dioxane, were determined for a very small particle size zinc oxide (ZnO) powder (median particle size approximately 23 nm) in the lower relative vapor pressure (P/Po) region. The ZnO samples for all adsorption measurements were dried at 400 degrees C for 4 h. A new method, which employed an FTIR spectrometer with a long path gas cell (IR path length of 3.0 m), was developed for the organic vapor adsorption measurements. The amount adsorbed was determined by mass balance. This method allows accurate quantification of organic vapors and is sensitive to very low P/Po values. The heptane and 1, 4-dioxane vapor adsorption isotherms appeared to exhibit the expected Type II behavior. The surface areas obtained for ZnO from BET analyses of the heptane and 1,4-dioxane vapor adsorption isotherms (36.9 and 30.3 m2/g) compared reasonably well to the surface area obtained from BET analysis of the nitrogen vapor adsorption isotherm (32.6 m2/g). The amount of vapor adsorbed by ZnO at P/Po equal to 0.1, in terms of number of moles, was observed to decrease in the order: water10 >> 1,4-dioxane > heptane. It was inferred that, while heptane was only adsorbed via a dipole-induced dipole interaction, 1,4-dioxane was physically adsorbed via an interaction dominated by the oxygen lone-pair orbital. Presumably, this interaction was more comparable to a weak dipole-dipole interaction. These results are consistent with the expected strengths of interaction.

Dioxanes↗
PubMed1980

A comparative study on the neurotoxicity of n-pentane, n-hexane, and n-heptane in the rat.

The neurotoxicity of n-pentane, n-hexane, and n-heptane have been studied in Wistar strain male rats after exposure to 3000 ppm of n-pentane, n-hexane, or n-heptane for 12 hours a day for 16 weeks. The nerve conduction velocity and the distal latency were measured before the beginning of the exposure and after exposure for four, eight, 12, and 16 weeks. The experiment showed that n-hexane disturbed the conduction velocity of the motor nerve and the mixed nerve and prolonged the distal latency in the rat's tail, but that n-pentane and n-heptane did not. The light and electron microscopic examination showed that the peripheral nerve, the neuromuscular junction, and the muscle fibre of the rats exposed to n-hexane were severely impaired, but those of the rats exposed to n-pentane or n-heptane showed no particular changes even after 16 weeks of exposure. These results show that n-hexane is far more toxic to the peripheral nerve of the rat than n-pentane or n-heptane. It is necessary to study the neurotoxicity of other petroleum hydrocarbons, since some reports suggest that petroleum solvents might possibly contain neurotoxic hydrocarbons other than n-hexane.

Animals↗
PubMed2003

4-oxa-1-azabicyclo[3.2.0]heptan-7-one derivatives as anti-tumor agents.

A series of naturally occurring and synthetic novel oxapenam (4-oxa-1-azabicyclo[3.2.0] heptan-7-one) derivatives with their antitumor activity and the structure-activity relationship among this class of compounds is reported. Among the synthetic 4-oxa-1-azabicyclo[3.2.0]heptan-7-one having an ester, amide, ether derivatives of hydroxy group at C-3 position exhibited either no activity or reduced the antitumor activity in vitro. The 3-amino acid 4-oxa-1-azabicyclo[3.2.0]heptan-7-one derivatives showed better antitumor activity than naturally occurring 4-oxa-1-azabicyclo[3.2.0]heptan-7-one derivative G0069A. The trans isomers exhibited superior stability and activity over the cis isomers at the 3- and 5-position. Some of these compounds showed strong cytotoxicity against P388 and KB cells with IC(50) value ranging from 0.004 to 0.6 micro g/ml and they did not show any cross resistance against ADR, 5-FU and VCR resistant cell lines in vitro. Of these, 3-hydroxy methyl, 3-(2-amino-2-carboxy-1-benzyloxy ethyl) and 3-(2-amino-2-carboxy ethyl) 4-oxa-1-azabicyclo[3.2.0] heptan-7-one inhibited 71-84% in vivo tumor growth of colon 26 and S-180 cells subcutaneously implanted into mice at a varying dose between 0.625-15 mg/kg/day depending upon the compounds and the tumor cell lines.

Animals↗
PubMed2005

Effect of Pt and Sn on the adsorption of n-heptane in gamma-Al2O3 catalyst models.

The Grand Canonical Monte-Carlo (GCMC) method has been used to carry out simulations of the adsorption of n-heptane in models of naphtha-reforming catalysts. Models used in the study differed in the number and distribution of metal atoms-Pt and Sn. The number of adsorbed n-heptane molecules grows linearly with increasing number of metal atoms. The effect of Pt content on the adsorption of n-heptane molecules is most distinct at approximately 100 kPa and within the lower range of the temperatures investigated. In the models of bimetallic catalysts, the effect of the two metals is additive. [Figure: see text]. Effect of Pt and Sn on number of n-heptane molecules adsorbed in Al2O3 catalyst in 773 K and 1000 kPa.

Adsorption↗
PubMed2002

Photocatalytic oxidation of heptane in the gas-phase over TiO2.

In this paper, gas-phase photocatalytic oxidation (PCO) of heptane over UV-illuminated TiO2 was carried out at ambient temperature in a batch reactor. Complete oxidation of heptane with almost stoichiometric production of CO2 and H2O was observed. The intermediates detected were propanal, butanal, 3-heptanone, 4-heptanone and carbon monoxide. A scheme of the possible mechanism for PCO of heptane over TiO2 was suggested. Langmuir-Hinshelwood kinetics equation was obtained from the results at different initial concentrations of heptane, oxygen, moisture and light intensity. The photocatalytic activity of TiO2 can be sustained indefinitely. This can be attributed to the production of water in the system, which can replenish the consumed hydroxyl radicals.

Algorithms↗