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PubMed2005

Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.

A novel technique, gas chromatography-UV spectrometry (GC-UV), was used to quantify volatile organic compounds (VOCs) in settled dust from 389 residences in Sweden. The dust samples were thermally desorbed in an inert atmosphere and evaporated compounds were concentrated by solid phase micro extraction and separated by capillary GC. Eluting compounds were then detected, identified, and quantified using a diode array UV spectrophotometer. Altogether, 28 compounds were quantified in each sample; 24 of these were found in more than 50% of the samples. The compounds found in highest concentrations were saturated aldehydes (C5-C10), furfuryl alcohol, 2,6-di-tert-butyl-4-methylphenol (BHT), 2-furaldehyde, and benzaldehyde. Alkenals were also found, notably 2-butenal (crotonaldehyde), 2-methyl-propenal (methacrolein), hexenal, heptenal, octenal, and nonenal. The concentrations of each of the 28 compounds ranged between two to three orders of magnitude, or even more. These results demonstrate the presence of a number of VOCs in indoor dust, and provide, for the first time, a quantitative determination of these compounds in a larger number of dust samples from residents. The findings also illustrate the potential use of GC-UV for analysing volatile compounds in indoor dust, some of which are potential irritants (to the skin, eyes or respiratory system) if present at higher concentrations. The potential use of GC-UV for improving survey and control of the human exposure to particle-bound irritants and other chemicals is inferred.

Air Pollution, Indoor↗
PubMed2004

Copper(II) Schiff base coordination compounds of dien with heterocyclic aldehydes and 2-amino-5-methyl-thiazole: synthesis, characterization, antiproliferative and antibacterial studies. Crystal structure of CudienOOCl2.

A new series of coordination compounds of the starting materials [Cu(dienX(2)Y(2))] and their adducts [Cu(dienXXY(2))(2a-5mt)] (where dien=diethylenetriamine, dienXX=Schiff bases of diethylenetriamine with 2-furaldehyde or 2-thiophene-carboxaldehyde, X=O, S, Y=Cl, Br, NO(3) and 2a-5mt=2-amino-5-methylthiazole) were synthesized by stepwise reactions and their structures were established by C, H, N, Cu analysis, spectroscopic, magnetic and molar conductivity measurements. The isolated compounds are monomers, paramagnetic and electrolytic compounds of the type 1:1. In all cases, the pentadentate Schiff base (dienXX) is bonded in a tridentate fashion through the 3 N atoms. In the CudienXXY(2) compounds the coordination sphere is completed by two Cl or Br or NO(3) groups in a square pyramidal arrangement. The proposed structure for this type of compound was further supported by X-ray diffraction analysis of the compound [Cu(dienOO)Cl(2)]. Its basal plane consists of three Cu-N contacts [2.017(2), 2.025(2) and 2.012(2) A] from dienOO, and the Cl(1) atom, while the Cl(2) atom possesses the apical position, the relevant distances being 2.2732(7) A for Cu-Cl(1) and 2.6051(7) A Cu-Cl(2). In the CudienX(2)Y(2).2a-5mt adducts the coordination sphere of copper is further completed by the nitrogen ring atom of the 2a-5mt, forming an octahedral configuration. The study of the biological activity of the compounds synthesized against a panel of different normal and cancer cell lines (MRC5, HeLa, MCF7, HT-29, OAW42, T47D) and bacteria (E. coli, B. cereus, B. subtilis) showed that the adducts of the type [Cu(dienXXY(2))(2a-5mt)] exhibit increased activity both in cancer cells and in bacteria, compared to the starting material of type [Cu(dienXXY(2))].

Aldehydes↗
PubMed2005

In vivo anticancer, anti-inflammatory, and toxicity studies of mixed-ligand Cu(II) complexes of dien and its Schiff dibases with heterocyclic aldehydes and 2-amino-2-thiazoline. Crystal structure of [Cu(dien)(Br)(2a-2tzn)](Br)(H(2)O).

A new series of complexes of the type [Cu(dien)(2a-2tzn)Y(2)] and [Cu(dienXX)(2a-2tzn)Y(2)], where dien=diethylenetriamine and dienXX=Schiff dibase of diethylenetriamine formed with 2-furaldehyde (dienOO), 2-thiophenecarboxaldehyde (dienSS), or pyrrol-2-carboxaldehyde (dienNN); Y=Cl, Br or NO(3); and 2a-2tzn=2-amino-2-thiazoline, were synthesized and their structure established by C, H, N and Cu analysis; IR and electronic spectra; magnetic susceptibility; and molar conductivity. The isolated complexes are monomers, paramagnetic, and electrolytes of types 1:1 or 1:2. In both types of solid state complexes, [Cu(dien)(2a-2tzn)Y(2)] and [Cu(dienXX)(2a-2tzn)Y(2)], dien and its Schiff dibases are bonded to Cu(II) in a tridentate fashion through 3N atoms. The coordination sphere is completed by the endocyclic nitrogen of the thiazoline moiety and by two Cl, Br, or NO(3) groups with distorted octahedral geometry. The proposed structure of these compounds was supported by X-ray analysis of [Cu(dien)(Br)(2a-2tzn)](Br)(H(2)O). The coordination polyhedron around the copper atom can be described as a distorted square pyramid [Cu(dien)(Br)(2a-2tzn)](+). Its basal plane is occupied by the four nitrogen atoms of the dien and thiazoline ligands with Cu-N distances ranging between 1.996(6) and 2.032(3)A, and the axial position is occupied by one of the two bromine atoms (Br1) with a Cu1-Br1 bond distance of 2.782(1)A. The second bromine atom (Br2) is 4.694(2)A from the copper atom, which exists as a discrete anion and is responsible for the cationic nature of the complex. Results regarding toxicity, antitumor, and anti-inflammatory activities of the investigated compounds are promising and allow the selection of a lead compound for further biological studies.

Animals↗
PubMed2002

Lanthanum(III)-catalyzed degradation of cellulose at 250 degrees C.

Lanthanum(III) chloride was found to effectively catalyze the degradation of cellulose in water at 250 degrees C. The degradation conversion of cellulose in the presence of a catalytic amount of lanthanum chloride reached 80.3% after 180 s, which corresponded to the turnover number of 83, whereas the reaction did scarcely proceed in the absence of the catalyst. The degradation products were separately quantified as water-soluble (WS), methanol-soluble (MS), methanol-insoluble (MI), and gaseous (G) products. The HPLC and GC analyses revealed that the WS materials are mainly composed of 5-hydroxymethyl-2-furaldehyde (HMF), D-glucose, and levulinic acid. Cellobiose, the disaccharide component of cellulose, was scarcely detected during the reaction.

Catalysis↗
PubMed2001

CoMFA-SIMCA model for antichagasic nitrofurazone derivatives.

The physico-chemical properties of some 5-nitro-2-furaldehyde semicarbazones (nitrofurazones) and thiophene analogues were compared with their in vitro and in vivo trypanocidal activity against Trypanosoma cruzi (Tulahuen strain). 3D-QSAR models were obtained by applying the SIMCA methodology to the electrostatic and steric fields (CoMFA fields) of the molecules. Nitrofurazones bearing N4 substituents. which cover a range of 14-17 A from the nitro group with a thickness of about 6 A when considering the extended conformer. produced complete survival in infected mice. The in vitro model allows larger N4 substituents than the SURVival model, but they must not bear positive centres in the region 15-16 A from the nitro group. Moreover, the in vitro model is in agreement with the active site of trypanothione reductase (TR). Both models can be of use in the design of novel drugs bearing an amide-like group at a distance of 7-9 A from an easily reducible group.

Animals↗
PubMed2002

Comparison of the evolution of low molecular weight phenolic compounds in typical Sherry wines: Fino, Amontillado, and Oloroso.

Changes in the content of low molecular weight phenolic compounds (hydroxybenzoic and hydroxycinnamic acids, aldehydes, and their esterified derivatives, tyrosol and 5-(hydroxymethyl)-2-furaldehyde) during the aging of three different classes of Sherry wine, Fino, Oloroso, and Amontillado, have been studied. The samples studied were taken from each of the scales of the particular aging system applied to the three classes of wine. Clear differences were observed in the behavior of the low molecular weight phenolic in the three classes of wine. The wines subjected to oxidative aging presented a higher phenolic content overall, with the exception of the esterified derivatives of phenolic compounds that are mainly found in the samples that have not undergone any process of oxidation. MANOVA results confirmed that there are significant differences between all of the samples of the three types of wines. Using LDA, a classification of 100% of the samples has been made.

Aldehydes↗
PubMed2003

Structural identification of nonvolatile dimerization products of glucosamine by gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and nuclear magnetic resonance analysis.

The degradation profile of glucosamine bulk form stressed at 100 degrees C for 2 h in an aqueous solution was studied. Column chromatography of acetylated product mixture led to isolation of two pure compounds (1b and 2b) and a mixture of at least three isomers (3b). 1a and 2a were identified as 5-(hydroxymethyl)-2-furaldehyde (5-HMF) and 2-(tetrahydroxybutyl)-5-(3',4'-dihydroxy-1'-trans-butenyl)pyrazine, respectively, by utilizing a variety of analytical techniques, such as GC-MS, LC-MS, on-line UV spectrum, (1)H and (13)C NMR, and DEPT, as well as (1)H-(1)H COSY. 3a was identified as 2-(tetrahydroxybutyl)-5-(2',3',4'-trihydroxybutyl)pyrazine, commonly known as deoxyfructosazine. In addition, glucosamine solid dosage form was exposed to 40 degrees C/75% relative humility for 10 weeks. Methanol extract of glucosamine solid dosage form was analyzed after acetylation by LC-MS, resulting in degradants 3b and 4b. 3a and 4a were, therefore, determined as deoxyfructosazine and 2,5-bis(tetrahydroxybutyl)pyrazine (fructosazine), respectively. Furthermore, the mechanisms of formation of identified degradation products are proposed and briefly discussed.

Chromatography, High Pressure Liquid↗
PubMed2003

Simultaneous quantitative analysis of maillard reaction precursors and products by high-performance anion exchange chromatography.

A new analytical setup allowing the simultaneous analysis of precursors and products of the Maillard reaction is described. It is based on high-performance anion exchange chromatography with electrochemical (ECD) and diode array detectors (DAD) coupled in series. Chromatography and detection were optimized to permit simultaneous monitoring of compounds relevant to the Maillard reaction, such as the sugar, the amino acid, and the corresponding Amadori compound as well as the cyclic intermediates 5-(hydroxymethyl)-2-furaldehyde, maltol, and 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one. Separation was achieved on a CarboPac PA-1 column using a gradient of sodium acetate in aqueous sodium hydroxide. The Amadori compound, glucose, and glycine were monitored by an ECD operating in the integrated amperometry mode. The number of analyzed compounds was further increased by coupling the ECD with a DAD for the analysis of ultraviolet-active constituents. This method was successfully applied to model Maillard reaction mixtures based on glucose and glycine.

Anions↗
PubMed1999

Phenolic constituents, furans, and total antioxidant status of distilled spirits.

The concentrations of 11 phenols and 5 furans were measured in 12 categories of distilled spirits by HPLC methodology, together with the total antioxidant status (TAS) of the same beverages. Ellagic acid was the phenol present in highest concentration in all beverages. Moderate amounts of syringaldehyde, syringic acid, and gallic acid, as well as lesser amounts of vanillin and vanillic acid, were measurable in most samples of whiskey, brandy, and rum but were largely undetectable in gin, vodka, liqueurs, and miscellaneous spirits. 5-(Hydroxymethyl)furfural was the predominant furan in the former three beverages, notably cognac, with 2-furaldehyde the next highest, but these were undetectable in most of the latter beverages. Highest TAS values were given by armagnac, cognac, and bourbon whiskey, all three of which tended toward the highest concentrations of phenols. Negative TAS values were exhibited by rum, vodka, gin, and miscellaneous spirits in line with the low or undetectable phenol concentrations in these beverages. Wood aging is the most likely source of phenols and furans in distilled spirits. Those beverages exposed to this treatment contain significant antioxidant activity, which is between the ranges for white and red wines, with the potential to augment the antiatherosclerotic functions attributable to the ethanol that they contain.

Alcoholic Beverages↗
PubMed1994

Synthesis and carbonic anhydrase inhibitory activity of 4-substituted 2-thiophenesulfonamides.

A series of 4-substituted 2-thiophenesulfonamides was prepared from 3-thiophenecarboxaldehyde using metalation chemistry developed for 3-furaldehyde. Several of these compounds inhibit carbonic anhydrase II in vitro at concentrations of less than 10 nM. In addition, none of these compounds exhibit sensitization potential as determined from in vitro measurement of cysteine reactivity.

Animals↗
PubMed1975

Substituted 1-[(5-nitrofurfurylidene)amino]-4-imidazolin-2-ones.

A series of 1-[(5-nitrofurfurylidene)amino]-4-imidazolin-2-ones has been prepared. A new synthesis of 4-alkyl-1-[(5-nitrofurfurylidene)amino]-4-imidazolin-2-ones involving the oxidative ring closure of 5-nitro-2-furaldehyde 2-(2-hydroxyethylalkyl)semicarbazones is described. The in vitro testing of the compounds against a variety of bacteria is reported.

Anti-Bacterial Agents↗
PubMed1975

Synthesis and antibacterial properties of methylsulfinyl and methylsulfonyl analongs of some nitrofurans.

The sulfoxides 5-methylsulfinyl-2-furaldehyde semicarbazone (2) and 1-[(5-methylsulfinyl-2-fufurylidene)amino]hydantoin (3) as well as the sulfones 1-[(5-methylsulfonyl-2-furfurylidene)animo]hydantoin (1) and 1-(5-methylsulfonly-2-furyl)-2-(6-amino-3-p-ridazyl)ethylene hydrochloride (4) have been prepared and tested for antibacterial activity against a number of gram-negative and gram-positive organisms. The compounds are much less active than the corresponding 5-nitrofuran derivatives, possibly because their reduction potentials are too negative for them to interfere with reductive enzyme systems within the bacteria.

Anti-Bacterial Agents↗
PubMed2003

Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement.

An enantiospecific synthesis of the phospholipase A(2) inhibitor (+)-(4R)-manoalide is reported in which all 25 carbons of the sesterterpenoid skeleton are constructed from 3-furaldehyde, trimethylalane, oxirane, CO, beta-ionone, and propargyl bromide. The overall yield for the longest linear sequence (12 steps) is 12%. Key steps include (a) a zirconium-catalyzed carboalumination reaction to construct the C10-C11 trisubstituted alkene, (b) a Cu(I)-mediated 1,2-metalate rearrangement to construct the C6-C7 trisubstituted alkene, (c) a Sharpless kinetic resolution to secure the (4R)-stereochemistry, (d) generation of a 5-stannyl-2,3-dihydrofuran by Mo-catalyzed cycloisomerization of a homopropargylic alcohol, and (e) construction of the hydroxyfuranone ring by photooxidation of a silylfuran.

Alkenes↗
PubMed2006

Effect of structure in benzaldehyde oximes on the formation of aldehydes and nitriles under photoinduced electron-transfer conditions.

The mechanistic aspects of the photosensitized reactions of a series of benzaldehyde oximes (1a-o) were studied by steady-state (product studies) and laser flash photolysis methods. Nanosecond laser flash photolysis studies have shown that the reaction of the oxime with triplet chloranil (3CA) proceeds via an electron-transfer mechanism provided the free energy for electron transfer (DeltaG(ET)) is favorable; typically, the oxidation potential of the oxime should be below 2.0 V. Substituted benzaldehyde oximes with oxidation potentials greater than 2.0 V quench 3CA at rates that are independent of the substituent and the oxidation potential. The most likely mechanism under these conditions is a hydrogen atom transfer mechanism as this reaction should be dependent on the O-H bond strength only, which is virtually the same for all oximes. Product studies have shown that aldoximes react to give both the corresponding aldehyde and the nitrile. The important intermediate in the aldehyde pathway is the iminoxyl radical, which is formed via an electron transfer-proton transfer (ET-PT) sequence (for oximes with low oxidation potentials) or via a hydrogen atom transfer (HAT) pathway (for oximes with larger oxidation potentials). The nitriles are proposed to result from intermediate iminoyl radicals, which can be formed via direct hydrogen atom abstraction or via an electron-transfer-proton-transfer sequence. The experimental data seems to support the direct hydrogen atom abstraction as evidenced by the break in linearity in the plot of the quenching rates against the oxidation potential, which suggests a change in mechanism. The nitrile product is favored when electron-accepting substituents are present on the benzene ring of the benzaldehyde oximes or when the hydroxyl hydrogen atom is unavailable for abstraction. The latter is the case in pyridine-2-carboxaldoxime (2), where a strong intramolecular hydrogen bond is formed. Other molecules that form weaker intramolecular hydrogen bonds such as 2-furaldehyde oxime (3) and thiophene-2-carboxaldoxime (4) tend to yield increasing amounts of aldehyde.

Journal Article↗
PubMed1998

Maillard reaction of lactose and fluoxetine hydrochloride, a secondary amine.

Analysis of commercially available generic formulations of fluoxetine HCl revealed the presence of lactose as the most common excipient. We show that such formulations are inherently less stable than formulations with starch as the diluent due to the Maillard reaction between the drug, a secondary amine hydrochloride, and lactose. The Amadori rearrangement product was isolated and characterized; the characterization was aided by reduction with sodium borohydride and subsequent characterization of this reduced adduct. The lactose-fluoxetine HCl reaction was examined in aqueous ethanol and in the solid state, in which factors such as water content, lubricant concentration, and temperature were found to influence the degradation. N-Formylfluoxetine was identified as a major product of this Maillard reaction and it is proposed that N-formyl compounds be used as markers for this drug-excipient interaction since they are easy to prepare synthetically. Many characteristic volatile products of the Maillard reaction have been identified by GC/MS, including furaldehyde, maltol, and 2,3-dihydro-3,5-dihydroxy-6-methyl-4 H-pyran-4-one. Close similarity between the degradation products of simple mixtures and formulated generic products was found; however, at least one product decomposed at a rate nearly 10 times that predicted from the simple models. Maillard products have also been identified in unstressed capsules. The main conclusion is that drugs which are secondary amines (not just primary amines as sometimes reported) undergo the Maillard reaction with lactose under pharmaceutically relevant conditions. This finding should be considered during the selection of excipients and stability protocols for drugs which are secondary amines or their salts, just as it currently is for primary amines.

Antidepressive Agents, Second-Generation↗
PubMed2000

Catalysis by amino acid-derived tetracoordinate complexes: enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes.

Me(2)Zn and Et(2)Zn added to aromatic and aliphatic aldehydes in the presence of 3 mol % of 2. (S)-1-Phenylethanol (91% ee) and (S)-1-phenylpropanol (86% ee) were synthesized from benzaldehyde and (S)-1-furan-2-yl-1-propanol (86% ee) from 2-furaldehyde. Nonanal and 3-phenylpropanal provided (S)-3-undecanol (96% ee) and (S)-1-phenyl-3-pentanol (94% ee). A solid-phase variant was effective with reduced ee's (e.g., 86% ee --> 79% ee) for (S)-1-phenylpropanol.

Journal Article↗
PubMed2002

Molecular characterisation of organic material in air fine particles (PM10) using conventional and reactive pyrolysis-gas chromatography-mass spectrometry.

Pyrolysis-gas chromatography-mass spectrometry (Py-GC-MS) was applied to study the composition of organic constituents in air particulate matter (PM10) collected inside an industrial area. A few milligrams of sampling filters containing air particles were pyrolysed at 700 degrees C directly (conventional) or after the addition of a derivatising reagent (tetramethylammonium hydroxide, TMAH, for pyrolysis-methylation; hexamethyldisilazane, HMDS, for pyrolysis-silylation). Py-GC-MS was also applied to synthetic polymers (poly(styrene-co-isoprene), polylimonene and polypinene) and vegetation samples (coniferous pollen, bark and resin) to identify markers indicative of possible precursors. Pyrolysates of PM10 showed the same suite of compounds in all the four seasons, dominated by hydrocarbons like styrene, limonene and clusters of isomeric alkenes with 14, 15 and 16 carbon atoms. Pyrolysis products of natural origin, including furaldehyde, benzeneacetonitrile, dehydroabietin and other diterpenoids were found, while no specific markers of synthetic rubbers were detected. The principal products released from reactive pyrolysis of PM10 were methyl or trimethylsilyl (TMS) derivatives of 1,6-anhydroglucose (levoglucosan), fatty acids, dehydroabietic acid and other resin acids along with hydroxy (di)carboxylic acids. Possible sources of the detected products (e.g. pine forest, biomass combustion) are discussed.

Aerosols↗
PubMed2003

Stereochemistry of intramolecular Diels-Alder furan (IMDAF) reactions of furyl-substituted chiral ethanolamides.

This paper describes the stereoselective outcome of the intramolecular Diels-Alder furan (IMDAF) reaction of substituted (2S,3S)-ethanolamides 9-13, which were synthesised from a furyl substituted cyanohydrin. The latter was obtained from 2-furaldehyde with high enantioselectivity by an oxynitrilase catalysed addition of hydrogen cyanide. The stereochemistry of the IMDAF products was shown to be dependent on the size of the ethanolamide substituents R. Small substituents (H, Me, CN) gave exclusively exo-cycloaddition, whereas more bulky ones (Ph, Et) gave both evo- and endo-addition, the larger phenyl substituent giving a high endo-exo-ratio.

Journal Article↗