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  • Organic Chemistry  (7.659)
  • Chemical Engineering  (4.742)
  • 1990-1994  (7.824)
  • 1965-1969  (4.577)
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  • 1
    Digitale Medien
    Digitale Medien
    Nitrostyrene Derivatives of Adenosine 5′-Glutarates Modified with an Alkyl Spacer and their inhibitory activity on epidermal growth factor receptor protein tyrosine kinase (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 59-69 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: β-Nitrostyrene derivatives of adenosine 5′-glutarates are potent and selective bisubstrate-type inhibitors of the epidermal growth factor receptor protein tyrosine kinase (EGF-R PTK). In an attempt to improve the inhibitory activity, this type of compounds was modified with alkyl spacers of varying length between the nitrostyrene and the glutaryl units. The spacers consisted of 1, 3, 4, and 5 atoms to give compounds of the benzyl, oxyethyl, oxypropyl, and oxybutyl series, respectively (Schemes 1 and 2). Adenosine 5′-esters were prepared in the benzyl and oxypropyl series only. Compared to the compounds in the parent series without spacer (IC50 = 0.7-12 μM), most of the modified compounds inhibited the EGF-R PTK only marginally or were inactive (IC50 ≥ 100 μM). The only exceptions were the free acids 19 and 20 with IC50 values of ca. 5 μM. It is noteworthy that esterification of these two hydrogen glutarates with either MeOH or adenosine yielded inactive compounds, which is in contrast to the corresponding substances without spacers.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770109
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  • 2
    Digitale Medien
    Digitale Medien
    Synthese und Eigenschaften der Furo- und Thieno-Analogen von PQQ-TriesterTeil einer Präsentation am ‘2nd International Symposium on PQQ and Quinoproteins’, 19.-22. Nov. 1991, Yamaguchi, Japan. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 100-110 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Synthesis and Characterization of the Furo and Thieno Analogues of the Triester of PQQWe report here the synthesis and properties of the furo and thieno analogues of 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9- tricarboxylic acid ( = PQQ), i.e. the furo- and thieno[2,3-f]quinoline-4,5-quinone (FQQ and TQQ, resp.) derivatives B and C, obtained as triesters. The triester of PQQ derivative A is much more stable than the triesters of B or C, and only the triester of A shows strong activity in nonenzymatic catalytic oxidations.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770113
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  • 3
    Digitale Medien
    Digitale Medien
    Computational Approach to the Receptor-Bound Conformation of Cyclosporin A (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 171-181 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The conversion of the conformation of cyclosporin A (CsA) observed in CHCl3 to the receptor-bound state is investigated by two molecular-mechanics methods, template forcing and dynamic forcing. The conformations of CsA in CHCl3 and complexed with LiCl in THF as determined by NMR are used as starting structures. The transition starting from the CsA/CHCl3-derived conformation is hindered by steric interactions of two side chains (MeBmt1 and Val5). While starting with the CsA/LiCl-derived conformation, the conversion is facile. It is illustrated that these calculations, which are of artificial character, using only the starting and final structures of the observed conformational transition during the receptor-binding event, allow an insight into the interactions between the substrates and receptor in terms of an induced fit.
    Zusätzliches Material: 6 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770120
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  • 4
    Digitale Medien
    Digitale Medien
    Electrochemical Study of Phase-Transfer Catalysis Reactions: The Williamson ether synthesis (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 231-242 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The transfer properties of the ionic species involved in the Williamson ether synthesis by phase-transfer catalysis were investigated using electrochemical techniques developed for the study of polarised liquid/liquid interfaces. This approach allows the measurement of the apparent partition coefficients of the transferring species. From these data, it is proposed that the role of the phase-transfer catalyst salt in the reaction mechanism is to establish a Galvani distribution potential difference between the two phases which in turn acts as the driving force for transferring the reactive aqueous ions to the organic phase.
    Zusätzliches Material: 5 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770125
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  • 5
    Digitale Medien
    Digitale Medien
    Synthesis of (R)- and (S)-5-(Hydroxymethyl)-3-isopropyloxazolidin-2-one, intermediates in the preparation of optically active β-blockers (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 252-256 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: 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.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770127
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  • 6
    Digitale Medien
    Digitale Medien
    Calorimetric Measurements of the Complexation of Cyclosporin A, Ascomycin, Fujimycin, and Rapamycin with Lithium Chloride and with an Immunophilin (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 291-305 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Solutions (2 ml) of small linear and cyclic peptides (4-11), of a peptolide containing nine amino acids and a lactate moiety (12), of the cyclic undecapeptide cyclosporin A (CS, 1), and of the macrolides ascomycin, fujimycin, and rapamycin (13-15) in THF were added to excess LiCl, LiBr, or LiClO4 (up to 3000 equiv. in 40 ml THF) in a calorimeter (calorimetric titration). The enthalpies of interaction measured are in the range of ΔH = -8 to -37 kcal/mol. A similar experiment was carried out with one of the binding proteins of cyclosporin, the human cyclophilin A, to give the thermodynamic parameters for the complexation ΔH = -16, ΔG° = -10 kcal/mol, and ΔS° = -20 cal/mol·deg. at 25° which corresponds to an equilibrium constant K = 2·107 l/mol, in good agreement with the result of independent measurements using different methods. NMR Measurements of the macrolides in (D8)THF containing LiCl show strong down-field shifts of signals of the H-atoms next to C=O and C-OH groups in these molecules.
    Zusätzliches Material: 4 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770129
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  • 7
    Digitale Medien
    Digitale Medien
    NMR of Terminal Oxygen. Part 13Part 12: [1].. 17O-NMR spectra of C-nitroso compounds, thionitrites and NO+ Ion: Resonance effects in O=N - X compounds and correlation with CD spectra (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 306-316 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The 17O-NMR signals of four true C-nitroso compounds 1-4 appear at particularly low field (1550-1265 ppm), whereas the dimers (azodioxy type) resonate at ca. 400 ppm and the ‘isonitroso compounds’ ( = quinone-oximes; 5 and 6) at ca. 250 ppm. S-Nitroso compounds ( = thionitrites; 8 and 9) show shift values of ca. 1300 ppm, not far from C - NO; the NO+ ion is much stronger shielded (474 ppm). The results, together with those for higher-shielded nitroso compounds X - NO (X = RO, R2N, Cl, O-) are discussed in terms of (a) resonance stabilization through n-donation from X(π-bond order, approximated by the known barriers of rotation around the X - N bond) and of (b) electronic excitation energies ΔE. The latter are approximated by long-wave (symmetry-forbidden) UV/VIS absorptions and confirmed, where available, by the maxima of the curves of circular dichroism (CD); the CD curve of thionitrite 9 has been measured. It is found that the δ(17O) values of X - NO depend both on bond order and on ΔE, which could not be separated. The higher shielding of NO+ compared with X - N=O is explained on the basis of anisotropy effects, which differ between sp and sp2 systems.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770130
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  • 8
    Digitale Medien
    Digitale Medien
    Masthead (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994) 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770101
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  • 9
    Digitale Medien
    Digitale Medien
    Enantioselective synthesis of (-)-conduramine C1 and aminobromocyclitol derivatives‘Naked Sugars’ as Synthetic Intermediates, Part XXV. Part XXIV, see [1a]; Part XXIII, see [1b]. (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 1-9 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: (1S,2R,6R,7R)-4-Phenyl-3,10-dioxa-5-azatricyclo[5.2.1.02,6]dec-4-en-9-one ((+)-5) obtained in 6 steps from the Diels-Alder adduct of furan to 1-cyanovinyl (1S)-camphanate ((+)-3) was reduced to the corresponding endo-alcohol (-)-6 the treatment of which with HBr/AcOH provided (-)-(3aS,4S,6R,7S,7aR)-4β-bromo-3aβ,4,5,6,7,7aβ-hexahydro-2-phenyl-1,3-benzoxazole-6β,7α-diyl diacetate ((-)-17). Elimination of HBr with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and acidic hydrolysis furnished (-)-(1R,2S,3R,4R)-4-aminocyclohex-5-ene-1,2,3-triol ( = (-)-conduramine C1;(-)-1).
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770103
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  • 10
    Digitale Medien
    Digitale Medien
    Nucleotides Part XLPart XXXIX: [1].. Synthesis and Characterization of Modified 2′-5′ Adenylate Trimers-Potential Antiviral Agents (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 10-22 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: 2′-5′ Adenylate trimers 41-44 carrying the (tert-butyl)dimethylsilyl (tbds) group at the 3′-OH position of various sugar moieties were synthesized via the phosphoramidite method. The use of the (tert-butyloxy)carbonyl (boc) and 2-(4-nitrophenyl)ethylsulfonyl (npes) groups for 2′-OH protection in neighbourhood to the 3′-O-tbds residue was compared during the synthesis of the target trimers. For other functional positions, the use of the 2-(4-nitrophenyl)ethyl (npe) and 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) blocking groups were favoured.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19940770104
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