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  • Organic Chemistry  (84)
  • 1995-1999  (39)
  • 1970-1974  (15)
  • 1965-1969  (10)
  • 1930-1934  (20)
  • 1
    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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  • 2
    Electronic Resource
    Electronic Resource
    Etude sur les dérivés benzoylés de l'indigo II (1934)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 17 (1934), S. 113-128 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19340170117
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  • 3
    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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  • 4
    Electronic Resource
    Electronic Resource
    Amines as leaving groups in nucleophilic aromatic substitution reactions. III.For Part II, see Ref. 2. Hydrolysis of 1-amino-2,4-dinitrobenzenes (1995)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 8 (1995), S. 113-120 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The kinetic study of the reaction of 1-pyrrolidino-2,4-dinitrobenzene, 1-piperidino-2,4-dinitrobenzene and 1-morpholino-2,4-dinitrobenzene with NaOH in the presence and absence of the amine leaving group was carried out in aqueous solutions at 25°C, giving 2,4-dinitrophenol as the only product. A mechanism involving the formation of σ complexes by addition of HO- or the amine to the unsubstituted positions of the aromatic ring is proposed. These complexes were found to react faster than the original substrates.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610080211
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  • 5
    Electronic Resource
    Electronic Resource
    The Stabilization Energy of [18] Annulene. A thermochemical determination (1974)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 57 (1974), S. 2276-2288 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The thermal rearrangement of [18]annulene in solution gives benzene and 1,2-benzo-1,3,7-cyclooctatriene. This reaction has been investigated using a differential scanning calorimeter and the associated enthalpy change has been measured. The enthalpy of the reaction (in the gase phase at 298°K) is \documentclass{article}\pagestyle{empty}\begin{document}$$ \Delta {\rm H}_{\rm r} \left({{\rm g},\,298^ \circ } \right) = - 50.7 \pm 5\,{\rm kcal mol}^{{\rm - 1}} $$\end{document} From this value and the enthalpies of formation of the reaction products, the enthalpy of formation of [18]annulene is obtained: \documentclass{article}\pagestyle{empty}\begin{document}$$ \Delta {\rm H}_{\rm f} \,^ \circ \left({{\rm 1,}\,{\rm g},\,298^ \circ } \right) = 124 \pm 5.5\,{\rm kcal mol}^{{\rm - 1}} $$\end{document} The stabilization energy of [18]annulene, defined as the difference between the enthalpy of formation of the hypothetical Kékulé [18]annulene (with single and double bonds of normal lengths) and the heat of formation of the real molecule is then \documentclass{article}\pagestyle{empty}\begin{document}$$ \Delta {\rm H}_{{\rm stab}{\rm .}} \left({\rm 1} \right) = 37 \pm 6\,{\rm kcal mol}^{{\rm - 1}} $$\end{document} a value close to the corresponding quantity found for benzene.The very large stabilization energy of [18]annulen (100 ± 6 kcal mol-1) previously reported in the literature, based on measurements of the heat of combustion, is not correct since the annulene is certainly oxidized in the bomb prior to combustion.The isodynamic conformational mobility of [18]annulene is not incompatible with a stabilization energy of 37 kcal mol-1; the activation enthalpy observed for this process (ΔH≠ = 16.1 kcal mol-1) indicates that the stabilization is not completely destroyed in the transition state.The mechanism of the thermolysis of [18]annulen, investigated by kinetic measurements and by analysis of the shape of the thermograms, is discussed.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19740570745
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  • 6
    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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  • 7
    Electronic Resource
    Electronic Resource
    Design and Synthesis of Potent Macrocyclic Benzolactam Growth Hormone SecretagoguesDedicated to the Memory of Professor Wolfgang Oppolzer.2Deceased March 15, 1996. (1997)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 80 (1997), S. 1244-1259 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of a variety of potent macrocyclic growth hormone secretagogues, i.e. 5, 9, 12, and 20-22, based on the known lead structure L-692,429 (1) is described. These conformationally constrained growth hormone secretagogues were prepared by joining the two essential pharmacophores, the amino-acid side chain at the 1H-1-benzazepine moiety and the 1,1′-biphenyl moiety with a variety of linkers. The most potent analog was found to be L-744,080 (21), a derivative in which a 2′-carboxamide moiety at 1,1-biphenyl is N,O-joined to the OH group of the (2-hydroxypropyl)amino-acid side chain by a C4 ester linker. This potent analog may be useful in determining the bound conformation of the benzolactam class of growth hormone secretagogues at the newly identified GHS receptor, L-744,080 (21) with an ED50 of 20 nM was up to fifty times more potent than the seco-acid precursor and 3-fold more potent than the parent 2′-tetrazole compound L-692, 429 (1).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19970800421
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  • 8
    Electronic Resource
    Electronic Resource
    Non-destructive Removal of the Bornanesultam Auxiliary in α-Substituted N-Acylbornane-10,2-sultanis under Mild Conditions: An efficient synthesis of enantiomerically pure ketones and aldehydes (1997)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 80 (1997), S. 1319-1337 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: α-Substituted N-acylbornane-10, 2-sultams 6, 9, and 10 can be converted into enantiomerically pure ketones 5. 13, and 14, respectively, via a two-step procedure involving a known mercaptolysis reaction followed by an [Fe(acac)3]-mediated coupling of the resulting S-benzyl thioesters with Grignard reagents. Furthermore, enantiomerically pure aldehydes 23 can be obtained from α-substituted N-acylbornane-10,2-sultams 6 via a one-step reduction with (i-Bu)2AIH. No epimerization at the α-chiral center is observed during the cleavage reaction whereby the chiral auxiliary, bornane-10,2-sultam 1 or ent-l, was recovered. By using this methodology, several natural products or precursors thereof can be prepared.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19970800502
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  • 9
    Electronic Resource
    Electronic Resource
    Origin of diastereoselectivity in the thermal [4+2] cycloadditions of dienophiles derived from Oppolzer's sultams: Steric vs. Stereoelectronic InfluencesPresented in part at the IXth Eur. Symp. Org. Chem., 18-23 June 1995, Warse, Poland.Dedicated to the memory of Professor Wolfgang von Oppolzer (1997)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 80 (1997), S. 146-172 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Comparative semi-empirical PM3 and ab initio STO 3-21G calculations on bornanesultam-derived dienophiles containing the structural moiety SO2—N—C(O)—X(α) = Y(β) suggest that, among the conformers of low energy, the thermodynamically less stable SO2/C(O)-syn,C(O)/X=Y-s-cis conformation is also reactive in terms of LUMO level and atomic coefficients. Furthermore, the X(α), Y(β) LUMO atomic coefficients are nonequivalent with respect to both X(α)-re and X(α)-si faces, and thus have, depending on the conformation, a matching or mismatching stereoelectronic influence with the co-operative steric effect. This dissymmetry is believed to result from the generalized anemone effect of the N lone pair, itself anomerically stabilized and directed, in the absence of crucial steric interactions, by the pseudo-axial anti-periplanar S=O bond. Five N-acyl-substituted bornanesultams arc discussed ((-)-1a: N-acryloyl, X=CH, Y=CH2; (-)-1b; N-crotonoyl, X=CH, Y=CHMe; (-)-1c: N-N′-fumaroyl, X=CH, Y=CH(C(O)-bornanesultam); 2a: N-glyoxyloyl, X=CH, Y=O; 2b: N-acylnitroso, X=N, Y=O). In this context, differences with toluenesultams 3 are pointed out. A previous report on N-(acylnitroso)-bornanesultam 2b is revisited, and the diastereoselectivity observed is shown to result from thermodynamic control.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19970800115
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  • 10
    Electronic Resource
    Electronic Resource
    Fluorescence Quenching of 2,2′-Bithiazole-Containing Calix[4]arenes by Copper(I). Access to the corresponding [ML2], [ML], and [M2L] copper(I) complexes (1997)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 80 (1997), S. 1229-1243 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The complexing behaviour of 2,2′-bithiazole-containing calix[4]arenes towards Cu1 was investigated. The extinction of the intrinsic blue fluorescence of the free ligands upon addition of stoichiometric amounts of the metallic salt was used as complexation probe. This extinction was directly related to the chelation of the metal and allowed the controlled synthesis of new mono- and dimetalic complexes which were fully characterized.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19970800420
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