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  • 1
    Electronic Resource
    Electronic Resource
    Monitoring the behaviour of 4-ketocyclophosphamide versus cyclophosphamide during capillary gas chromatography by mass spectrometry (1987)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 14 (1987), S. 643-647 
    Details
    ISSN: 0887-6134
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Capillary Gas Chromatography (CGC) is capable of determining underivatized cyclophosphamide (CPA) using SCOT OV 275 columns. Then CPA is subjected to in situ degradation resulting in formation of a cyclization product which can be determined selectively in biological fluids. In routine bioanalysis however cyclization products of CPA metabolites might interfere, e.g. 4-keto CPA. In the present study possible formation of cyclization products of 4-keto CPA similar to CPA was monitored by Mass Spectrometry. Cyclization of 4-keto CPA in situ was demonstrated to occur, resulting in a product similar to that of CPA. Both cyclization products could be determined selectively and it appeared that in situ cyclization of 4-keto CPA was negligible (〈5%), probably owing to extra stabilization of the CPA metabolite by keto-enol tautomerism as has been demonstrated by NMR.
    Additional Material: 14 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bms.1200141113
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  • 2
    Electronic Resource
    Electronic Resource
    A CP-MAS NMR study of some deactivation methods in capillary gas chromatography (1984)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 7 (1984), S. 607-614 
    Details
    ISSN: 0935-6304
    Keywords: Gas chromatography, GC ; Fused silica capillary columns ; CP-MAS NMR ; Silylation ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The effect of temperature, water content, and the type of reagent on the silylation of fused silica capillaries was studied by 29Si and 13C CP-MAS NMR. Fumed silica (Cab-O-Sil M5), which is essentially a highly dispersed vitreous quartz with a surface comparable to that of fused silica capillary columns, was selected as a model material.Hexamethyldisilazane (HMDS) and 1,2-diphenyl-1,1,3,3-tetraphenyldisilazane (DPTMDS), which were used as silylation reagents, yielded trimethyl- and dimethylphenylsilyl surface groups respectively at lower temperatures (〈 350°C and 〈250°C respectively). At higher temperatures, increasingly more dimethylsilyl groups are formed, with the silicon bound to two oxygen atoms. This process occurs for DPTMDS at a considerably lower temperature than for HMDS. The formation of silyl groups on the surface and the disappearance of hydroxyl groups are followed independently. The 13C NMR and GC-MS of the reaction products showed that with DPTMDS, the formation of two Si-O-Si links is accompanied by a loss of phenyl groups rather than of methyl groups.After the Cab-O-Sil had been dried over P2O5, the formation of these double links occurred for HMDS only at temperatures above 460°C and for DPTMDS at 400°C. Thus we concluded that water supplies oxygen atoms for double Si-O-Si links (possibly crosslinks) necessary for efficient deactivation. This may explain the less successful silanization of fused silica capillaries because their water content is lower than that of glass capillaries.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240071102
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  • 3
    Electronic Resource
    Electronic Resource
    A study of some deactivation methods for fused silica capillary columns by CP-MAS NMR and capillary gas chromatography (1985)
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 8 (1985), S. 664-672 
    Details
    ISSN: 0935-6304
    Keywords: Gas chromatography, GC ; Fused silica capillary columns ; CP-MAS NMR ; Deactivation methods ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The effect of deactivating a fused silica surface by silylation with 1,1,3,3-tetraphenyl-1,3-dimethylilazane (TPDMDS), triphenylsilylamine (TPSA), and octamethylcyclotetrasiloxane (D4) and by polydimethylsiloxane degradation (PSD) is studied. Rehydrated, dried, and deactivated Cab-O-Sil M5 samples are used as model materials for 29Si CP-MAS NMR analysis.At about 350 °C, TPDMDS yelds mainly diphenylmethylsiloxysilane, dimethyldisiloxysilane, and triphenylsiloxysilane groups. TPSA yields phenyltrisiloxysilane, diphenyldisiloxysilane, and triphenylsiloxysilane groups. At 400°C, the products formed initially are eventually replaced by methyltrisiloxysilane or phenyltrisiloxysilane groups, while a substantial number of silanol groups still remains. The possible consequences for wettability are discussed.D4 reacts with Cab-O-Sil even at 200°C, but a large number of silanol groups remains. This number decreases gradually at higher temperatures and becomes negligible above 400°C. The formation of methyltrisiloxysilane groups, which starts at 425°C, is predominant at 490°C.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jhrc.1240081005
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  • 4
    Electronic Resource
    Electronic Resource
    Identification of oplopanonyl acetate isolated from Chamaecyparis pisifera (1990)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 28 (1990), S. 1030-1034 
    Details
    ISSN: 0749-1581
    Keywords: 2D NMR ; Oplopanonyl acetate ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oplopanonyl acetate was isolated from Chamaecyparis pisifera. Its structure and stereochemical features were established using NMR techniques.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1260281207
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  • 5
    Electronic Resource
    Electronic Resource
    Maravuic acid, a new seco-labdane diterpene from Croton matourensis (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 709-710 
    Details
    ISSN: 0947-3440
    Keywords: Diterpenes ; Croton matourensis ; seco-Labdanes ; Supercritical fluid extraction ; Structure elucidation ; 1D and 2D carbon-13 and proton NMR ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new seco-labdane diterpene, maravuic acid, has been isolated by supercritical fluid extraction using CO2 from the bark of Croton matourensis Aubl. (Euphorbiaceae). Its structure was elucidated by one and two dimensional NMR methods as (12E)-3,4-seco-labda-4(18),8(20),12,14-tetraen-3-oic acid 2.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199504103
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  • 6
    Electronic Resource
    Electronic Resource
    Mass spectrometric characterization of different norandrosterone derivatives by low-cost mass spectrometric detectors using electron ionization and chemical ionization (1990)
    New York, NY : Wiley-Blackwell
    Rapid Communications in Mass Spectrometry 4 (1990), S. 181-185 
    Details
    ISSN: 0951-4198
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Physics
    Notes: The abuse of nortestosterone in sport is an important problem in doping-control analysis. In order to detect the main urinary metabolite of nortestosterone, norandrosterone (NA), sensitive and specific methodology is necessary. In this context the use of a low-cost mass spectrometric detector such as the Finnigan MAT ion-trap detector (ITD) was studied. The electron ionization (EI) and positive-ion chemical ionization (PICI) mass spectra of the methoxime-trimethylsilyi, trimethylsilyl-enol trimethylsilyl ether and pentafluoropropionic ester derivatives of NA are described. The limits of detection of these derivatives are compared with those obtained by the Hewlett-Packard mass selective detector (MSD), another low-cost mass spectrometric detector and operating only in the EI mode. For the derivatives of the reference standard of NA the ITD has in the EI mode the same limit of detection, in the range of 0.5 to 1 ng injected on the column, as the MSD. However, under these conditions the ITD provides more spectrometric information, because it gives full scan data. Moreover, with the same or even improved limits of detection the ITD can operate in the PICI mode. On the other hand, for the analysis of NA isolated from urine samples, the performance of the MSD was better than that of the ITD. The ion trapping technique is probably limited when the chemical background is high.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/rcm.1290040604
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis and pharmacological investigation of stereoisomeric muscarines (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 4 (1992), S. 230-239 
    Details
    ISSN: 0899-0042
    Keywords: total synthesis ; chiral muscarines ; iodocyclization process ; muscarinic receptor subtypes M1, M2, and M3 ; affinity states ; eudismic ratio ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the eight stereoisomers of muscarine has been efficiently accomplished by utilizing the two enantiomers of lactic esters as starting material. The synthetic strategy is based on a SnCl4-catalyzed addition of allyltrimethylsilane to O-protected lactic aldehydes followed by an iodocyclization process. All the final derivatives possess an enantiomeric excess higher than 98%. The four pairs of enantiomers bound to M1, M2, and M3 muscarinic receptor subtypes in membranes from cerebral cortex, heart, and salivary glands, respectively, and recognized heterogeneous states of the receptors. Of the eight isomers, only natural muscarine (+)-1 recognized three affinity states of the M2 receptor. The compound was also the only one to show selectivity in the binding study, demonstrating 37- to 44-fold higher affinity for the M2 than for the M1 or M3 receptors. In addition, the compounds were tested in functional assays on isolated guinea pig atria (M2 receptors) and ileum (mixed population of M2 and M3 receptors) and their muscarinic potencies were determined. Among the eight isomers, again only (+)-1 enantiomer was found to be very active on both tissues. Its potency was more than two orders of magnitude higher than that of its enantiomer (-)-1 as well as the other six isomers. The eudismic ratios (E.R.) deduced from the two functional tests were 324 and 331. © 1992 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530040406
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  • 8
    Electronic Resource
    Electronic Resource
    Toxic doses of rac-, (-)-(S)- and (+)-(R)-propranolol in rats and rabbits (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 411-417 
    Details
    ISSN: 0899-0042
    Keywords: rac-propranolol ; enantiomers ; drug intoxication ; cardiovascular function ; respiratory function ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The contribution of the individual enantiomers ([+]-[R]- and [-]-[S]-propranolol) to rac-propranolol intoxication was studied in anaesthetized, spontaneously breathing (SB) rats and artificially ventilated (AV) rats and rabbits. In the SB rat, propranolol (30 mg.kg-1.h-1 i.v.) decreased heart rate and mean arterial blood pressure and caused hypoventilation, serious hypoxaemia, respiratory acidosis, and death by respiratory arrest. Survival time (ST) in the (+)-(R)-propranolol group (ST 91 ± 5 min) was significantly longer than in the rac-propranolol group (ST 68 ± 6 min). In AV rats and rabbits toxic doses of rac-, (-)-(S)- and (+)-(R)-propranolol, 30 mg.kg-1.h-1 and 15 mg.kg-1.h-1 i.v., respectively, induced comparable effects on haemodynamic variables as in the SB rat. Artificial ventilation lengthened ST by a factor of three to four in rats. In the AV rat, ST's were not significantly different between the rac-, (-)-(S)- and (+)-(R)-propranolol groups. In the rabbit, as in the SB rat, ST in the (+)-(R)-propranolol group was significantly longer than ST's in the rac- and (-)-(S)-propranolol groups. The acute respiratory acidosis in SB rats and the prolonged ST in AV rats suggest that respiratory failure is the primary and cardiovascular failure the secondary cause of death in propranolol intoxication. The potentiation of the toxic effect of the enantiomers observed after dosing the racemate instead of the pure enantiomers could not be explained by a stereoselective difference in plasma propanolol concentration. © 1996 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis and Biological Evaluation of 2-(2-Deoxy-β-D-ribofuranosyl)pyridine-4-carboxamideDedicated to Prof. Frank Alderweireldt on the occasion of his 61st birthday (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 1613-1620 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new protected 2-deoxy-D-ribose derivative, 5-O-[(tert-butyl)diphenylsilyl]-2-deoxy-3,4-O- isopropylidene-aldehydo-D-ribose (5), was synthesized starting from 2-deoxy-D-ribose. This compound was coupled with 2-lithio-4-(4,5-dihydro-4,4-dimethyloxazol-2-yl)pyridine giving a D/L-glycero-mixture 7 of 5-O-[(tert-butyl)diphenylsilyl]-2-deoxy-1-C-[4-(4,5 -dihydro-4,4-dimethyloxazol-2-yl)pyridin-2-yl]-3,4-O-isopropylidene- D-erythro-pentitol. The mixture 7 was 1-O-mesylated with methanesulfonyl chloride and subsequently treated with CF3COOH/H2O and ammonia to afford the α/β-D-anomers 10 of 2-(2-deoxy-D-ribofuranosyl)pyridine-4-carboxamide. Both anomers were purified and separated by HPLC and identified by NMR and DCI-MS. Anomer β-D-10 was evaluated against a series of tumor-cell lines and a variety of viral strains. No antitumor or antiviral activity was observed.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750516
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis of 2′-Deoxy-5-(isothiazol-5-yl)uridine and Its Interaction with the HSV-1 Thymidine Kinase (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1462-1474 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2′-Deoxy-5-(isothiazol-5-yl)uridine (12) was synthesized starting from 2′-deoxy-5-iodouridine using a Pd-catalysed cross-coupling reaction with propiolaldehyde diethyl acetal followed by deprotection and ring closure using thiosulfate. 2′-Deoxyuridine 12 has a particular place among the 5-heteroaryl-substituted 2′-deoxyuridines in that it has a high affinity for herpes simplex virus type 1 (HSV-1)-encoded thymidine kinase (TK) without antiviral activity. Biochemical studies revealed that 12 is a substrate for viral TK. We further investigated the interaction of 12 with the HSV-1 thymidine kinase. The conformation of 12 in solution was established by NMR spectroscopy. The most stable conformer 12A has the S-atom of the isothiazole ring placed in the neighbourhood of the C(4)=O group of the pyrimidine moiety. The compound was docked in its most stable conformation in the active site of HSV-1 TK and subjected to energy minimization. This demonstrated that the isothiazole moiety binds in a cavity lined by the side chains of Tyr-132, Arg-163, Ala-167, and Ala-168 and that the C(3) atom of the isothiazole moiety is located in close proximity of the phenolic O-atom of Tyr-132 and the aliphatic part of the Arg-163 side chain.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790519
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