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  • 1
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of 2′-benzamido-2′-deoxyadenosine analogues were synthesized in an effort to find new lead structures for the treatment of sleeping sickness. The 2′-deoxy-2′-(3-methoxybenzamido)adenosine (1h) was proved to be a selective inhibitor of the parasite glyceraldehyde 3-phosphate dehydrogenase which confirms the modeling studies. The solution-state conformation of 2′-(thiophene-2-carboxamido) analogue 1d demonstrates a 2′-endo conformation, an orientation of the thiophene ring under the ribose moiety, and the base part occupying a ‘syn’/‘anti’ equilibrium.
    Additional Material: 3 Ill.
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  • 2
    ISSN: 0947-3440
    Keywords: L-glycero-α-D-manno-Heptopyranosides ; Ethanolamine phosphates ; Phenylacetyl, enzymatic cleavage of ; Carbohydrates ; Glucosylations ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Immobilized penicillin-G acylase mediated removal of the N-phenylacetyl protective group in ethanolamine phosphates 7 and 9 furnished compounds 8 and 10, respectively. Deblocking of N-phenylacetyl-protected ethanolamine phosphate heptosyl disaccharide 22, a protected spacer-containing fragment of the inner-core lipopolysaccharide region of Neisseria meningitidis, immunotype L3 was readily accomplished with penicillin-G acylase, yielding target dimer 2. Disaccharide 22 was accessible by elongation of ethyl 1-thio-L-glycero-α-D-manno-heptopyranosyl donor 13 with acceptor 14 under the influence of N-iodosuccinimide/triflic acid. Protective group manipulations, phosphorylation with the reagent 2-cyanoethyl 2-(phenylacetylamino)ethyl N,N-diisopropylphosphoramidite (5) and deprotection furnished LD-Hepp dimer 22.
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  • 3
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 367-379 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of isoalloxazine and alloxazine derivatives have been investigated by 13C-NMR. The synthesis of selectively 13C-enriched derivatives made it possible to assign unambiguously the signals due to the quaternary carbon atoms at position 4, 4a and 10a of the isoalloxazine ring system. The assignment of the other resonances was ensured by the use of selectively deuteriated and chemically modified compounds as well as by decoupling techniques. The assignments differ in part from those published by Breitmaier & Voelter [2] on FMN and FAD. The solvent dependence of the resonances has been studied in dioxan/water mixtures. The experimental data are compared with published MO calculations and discussed.
    Additional Material: 3 Ill.
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  • 4
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 195Pt-, 31P- and 15N-NMR. data are presented for [PtCl2 (t-Bu 15N=CH—CH=15N (t-Bu)) (η2-styrene)] (1), trans-[{PtCl2 (PBu3)}2 (t-Bu 15N=CH—CH=15N (t-Bu))] (2), trans-[PtCl2 (t-Bu 15N=CH—CH=15N (t-Bu)) (PBu3)] (3) and various complexes of the type trans-[PtCl2 (N-ligand) (PBu3)]. In solution the gross structural features of 1 and 2 are shown to be in agreement with those found in the solid state; namely, 1 contains five-coordinate Pt and 2 is dinuclear. In 3 Pt is four-coordinate with only one N-atom of the diimine ligand being coordinated at -50° in CD2Cl2. The NMR. data for 2 and 3 are compared with those of trans-[PtCl2 (N-ligand) (PBu3)] (N-ligand = pyridine, 2, 6-dimethylpyridine, (15N)-hexylamine, (15N)-t-butylamine and (15N)-aniline) and are discussed in terms of the donor and acceptor properties of the N-ligands.
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  • 5
    ISSN: 0947-3440
    Keywords: Biscalix[4]arene ; Lanthanide ions ; Energy transfer ; Luminescence ; Dinuclear complexes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Three types of lower-lower rim linked biscalix[4]arenes that contain carboxylic ester (1) and/or amide functions (2 and 3) at their remaining phenolic oxygen atoms were synthesized. The homo- and heterodinuclear lanthanide ion complexes based on these ligands were used to study the energy transfer between different lanthanide ions. Photophysical studies comparing the luminescence properties of the homodinuclear Eu3+ complex and the heterodinuclear Eu3+-Nd3+ complex of 2 indicated that energy transfer is likely to occur from Eu3+ to Nd3+ with an efficiency of 〉 50%. The luminescence properties turned out to be strongly solvent dependent, which is attributed to structural changes leading to different positions of the lanthanide ions in the cavities provided by the biscalix[4]arene.
    Additional Material: 3 Ill.
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  • 6
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Choline Phosphatides, VI1).3-Palmitoyl-glycerol-I-phosphorylcholine (D-α-LySO-lecithin) and its Inactivity as Substrate for AcyltransferasesEnzyme reactions controlling the content of the strong lytic agent lysolecithin (monoacylglycerol-3-phosphorylcholine) in cell membranes, i. e. by degradation or by reacylation, are of great importance for the living cell. Lysolecithins, well defined with respect to configuration and structure, can be used as substrates for studying the metabolic fate of these compounds in membranes. Five of the six theoretically possible isomers of lysolecithin have been prepared by De Haas and Van Deenen (1965). - In this paper the synthesis of the hitherto unknown 3-acyl-glycerol-I-phosphorylcholine (B) is described. 3,4-lsopropylidene-D-mannitol (1) has been benzylated to give 1,2,5,6-tetrabenzyl-3,4-isopropylidene-D-mannitol (2). Acid hydrolysis
    Notes: Als Modellsubstanzen für biologische Untersuchungen sind einheitliche, konfigurativ eindeutige Lysolecithine von allgemeinem Interesse. Wir beschreiben erstmals die Synthese eines 3-Acyl-glycerin-1-phosphorsäurecholinesters (B) 3.4-Isopropyliden-D-mannit (1) wird zur Tetrabenzyl-Verbindung 2 benzyliert. Saure Hydrolyse von 2 ergibt 1.2.5.6-Tetrabenzy-D-mannit (3), der mittels Bleitetraacetat zu 1.2-Dibenzyl-glycerinaldehyd (4) Gespalten wird. Reduktion von 4 mit Lithiumalant führt zum 1.2-Dibenzyl-glycerin(5), das durch Veresterung mit Palmitinsäurechlorid das 3-Palmitoryl-Dibenzyl 6 liefert. Aus 6 erhält man bei der katalytischen Hydrogenolyse 2-Benzyl-und 1-Benzyl-3-palmitoyl-glycerin (7bzw. ),die chromatographisch getrennt werden . die Phosphorylierung von 7 mittels ß-Brom-äthyl-dichlorphosphat und die nachfolgende Behandlung mit Trimethylamin ergeben 3-Palmitoyl 2-benzyl-glycerin-1-phosphorylcholin (9), das durch katalytische Hydrogenolyse in 3-Palmitoyl-glycerin-1-phosphorylcholin (10) umgewandelt wird. - Das so dargestellte D-αLysolecithin erweist sich im Gegensatz zu 1 -Palmitoyl-glycerin-3-phosphorylcholin (L-α-Lyso-lecithin) nicht als Substrat für Acyl-CoA : Acylglycerinphosphorylcholin-Acyltransferasen,
    Additional Material: 1 Ill.
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  • 7
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 64 (1981), S. 2183-2188 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The conformational behaviour of sulpiride has been investigated by the quantum mechanical PCILO method and by CD. measurements. The results indicate the predominance of a folded, intramolecularly H-bonded conformer, with extended conformers being only slightly less stable. The pharmacological relevance of these results is briefly discussed.
    Additional Material: 3 Ill.
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  • 8
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 715-723 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Electronic properties of dopamine were studied by the ab initio STO-3G MO method. The molecular electrostatic potential (MEP) around the aromatic ring and the catechol group remains practically the same in 3,4-dihydroxytoluene (a model compound) and in neutral dopamine examined in its two extended conformations, namely that found in the crystal (side-chain and aromatic ring almost perpendicular) and the one corresponding to 2-amino-6,7-dihydroxytetralin (6,7-ADTN) (side-chain and aromatic ring almost coplanar). In protonated dopamine and in dopamine hydrochloride, the electrostatic potential of the catechol moiety is overshadowed by the positive charge, but the main features remain discernible. The catechol moiety was examined in its two coplanar conformations containing a ‘flip-flop H-bond’. The electrostatic potential around the catechol moiety is quite complex, with alternating positive and negative maxima. At increasing distances above and away from the catechol moiety, only two peripheral maxima, one negative and one positive, remain perceptible. The ‘flip-flop’ mechanism results in an approximate interchange of these two potential maxima, a fact which tends to level out the structural differences between the α- and β-rotamer of dopamine. Based on these results and on the structure of rigid agonists, some pharmacophoric features of dopamine agonists are proposed.
    Additional Material: 8 Ill.
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  • 9
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The (R)- and (S)-5-(hydroxymethyl)-3-isopropyloxazolidin-2-ones, ((R)- and (S)-2, resp.), pivotal intermediates in the preparation of optically active β-blockers, were synthesized using (R,E)-2-hydroxypent-3-enenitrile (1) as the chiral starting material. In the synthesis of (R)-2, a known cyclization/inversion step was applied.
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  • 10
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: N-Aminoalkylbenzamides and N-aminoalkyl-o-methoxybenzamides have been prepared and examined for their pKa, log P and dopamine receptor affinity. The pKa values range from ca. 7.5 for the derivatives having a one-C-atom side-chain, to ca. 10.3 for the N-aminobutyl derivatives. These variations with chain length are satisfactoryly explained by a field model. The variations in (log P)-values as a function of chain length and substitution at the N-atom indicate the involvement of proximity and conformational effects. The complete inability of the compounds to displace 3H-spiperone and 3H-sulpiride from their specific rat striatal binding sites demonstrates the critical role of adequate aromatic substitution at positions 4 and 5.
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