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0036025627
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See, for example:
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See, for example:. Klod S., Koch A., and Kleipenter E. J. Chem. Soc., Perkin Trans. 2 (2002) 1506
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Klod, S.1
Koch, A.2
Kleipenter, E.3
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3
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0011190497
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See, for example:
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See, for example:. Schleyer P.v.R., Maerker C., Dansfeld A., Jiao H., and Hommes N.J.R.v.E. J. Am. Chem. Soc. 118 (1996) 6317
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Schleyer, P.v.R.1
Maerker, C.2
Dansfeld, A.3
Jiao, H.4
Hommes, N.J.R.v.E.5
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6
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33847800907
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The shift occurring on the resonances of a carbon (upfield) and the attached protons (downfield) when a substituent is placed with a γ-gauche arrangement; after the original interpretation, which emphasized the steric interactions between hydrogen atoms and the C(γ) carbon atom (
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The shift occurring on the resonances of a carbon (upfield) and the attached protons (downfield) when a substituent is placed with a γ-gauche arrangement; after the original interpretation, which emphasized the steric interactions between hydrogen atoms and the C(γ) carbon atom (. Eliel E.L., Bailey W.F., Kopp L.D., Willer R.L., Grant D.M., Bertrand R., Christensen K.H., Walling D.K., Duch M.W., Wenkert E., Schell F.M., and Cochran D.W. J. Am. Chem. Soc. 97 (1975) 322
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Eliel, E.L.1
Bailey, W.F.2
Kopp, L.D.3
Willer, R.L.4
Grant, D.M.5
Bertrand, R.6
Christensen, K.H.7
Walling, D.K.8
Duch, M.W.9
Wenkert, E.10
Schell, F.M.11
Cochran, D.W.12
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8
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0001496662
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), the stereoelectronic origin of this effect still remains unknown ( )
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), the stereoelectronic origin of this effect still remains unknown (. Barfield M. J. Am. Chem. Soc. 117 (1995) 2862 )
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(1995)
J. Am. Chem. Soc.
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Barfield, M.1
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16
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4244095036
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Belanger-Giarepy F., Brisse F., Harvey P.D., Butler I.S., and Gilson D.F.R. Acta Crystallogr., Sect. C 43 (1987) 756
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Acta Crystallogr., Sect. C
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Belanger-Giarepy, F.1
Brisse, F.2
Harvey, P.D.3
Butler, I.S.4
Gilson, D.F.R.5
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20
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37049104893
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Duddeck H., Hollowood F., Karim A., and McKervey M.A. J. Chem. Soc., Perkin Trans. 2 (1979) 360
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J. Chem. Soc., Perkin Trans. 2
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Duddeck, H.1
Hollowood, F.2
Karim, A.3
McKervey, M.A.4
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22
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33847042471
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3 solution of amine 5 (50 mg) with TFA (two drops) inside the NMR tube and the mixture was left to equilibrate for several weeks before recording the NMR spectra; compounds 7 and 8 were prepared according to Ref. 11a.
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Between the numerous synthesized aminoadamantane derivatives, 2-alkyl-2-adamantanamines (e.g., compounds 2-5, 7, 8) were the most potent in vitro. For some representative examples see:
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Between the numerous synthesized aminoadamantane derivatives, 2-alkyl-2-adamantanamines (e.g., compounds 2-5, 7, 8) were the most potent in vitro. For some representative examples see:. Kolocouris N., Kolocouris A., Foscolos G.B., Fytas G., Neyts J., Padalko E., Balzarini J., Snoeck R., Andrei G., and De Clercq E. J. Med. Chem. 39 (1996) 3307
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Kolocouris, N.1
Kolocouris, A.2
Foscolos, G.B.3
Fytas, G.4
Neyts, J.5
Padalko, E.6
Balzarini, J.7
Snoeck, R.8
Andrei, G.9
De Clercq, E.10
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0345444664
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Zoidis G., Kolocouris N., Fytas G., Foscolos G.B., Kolocouris A., Fytas G., Karayannis P., Padalko E., Neyts J., and De Clercq E. Antiviral Chem. Chemother. 14 (2003) 155
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Antiviral Chem. Chemother.
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Zoidis, G.1
Kolocouris, N.2
Fytas, G.3
Foscolos, G.B.4
Kolocouris, A.5
Fytas, G.6
Karayannis, P.7
Padalko, E.8
Neyts, J.9
De Clercq, E.10
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25
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0038025788
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Stylianakis I., Kolocouris A., Kolocouris N., Fytas G., Foscolos G.B., Padalko E., Neyts J., and De Clercq E. Bioorg. Med. Chem. Lett. 13 (2003) 1699
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Bioorg. Med. Chem. Lett.
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Stylianakis, I.1
Kolocouris, A.2
Kolocouris, N.3
Fytas, G.4
Foscolos, G.B.5
Padalko, E.6
Neyts, J.7
De Clercq, E.8
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Kolocouris, A.; Broadhurst, R. W.; Zikos, C. Bioorg. Med. Chem. Lett., submitted for publication.
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13C spectra of some 2,2-disubstituted adamantanes have been analyzed (
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13C spectra of some 2,2-disubstituted adamantanes have been analyzed (. Krishnamurthy V., Iyer P.S., and Olah G.A. J. Org. Chem. 48 (1983) 3373
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(1983)
J. Org. Chem.
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Krishnamurthy, V.1
Iyer, P.S.2
Olah, G.A.3
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MM3 (J. Am. Chem. Soc. 1993, 115, 11918) and MMFF94 (J. Comp. Chem. 1996, 17, 587) force fields are implemented in pcmodel (version 9.0), Serena Software.
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1H correlation experiments a relaxation delay of 2 s was used; 2D NOE phase sensitive experiments were run using a mixing time of 1.5 s.
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The interaction of groups that are close in space normally results in shielding of the carbon and deshielding of the protons involved. A remarkable demonstration of a steric compression effect is the δ- or ε-effect on the proton chemical shifts in some tetracyclic norbornyl systems, where the repulsion between groups separated by four or five bonds is so severe that the compressed proton appears uncommonly downfield by 3.1-3.5 ppm, but also, the uncompressed proton moves compensatingly upfield by 0.8-0.9 ppm ( )
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The interaction of groups that are close in space normally results in shielding of the carbon and deshielding of the protons involved. A remarkable demonstration of a steric compression effect is the δ- or ε-effect on the proton chemical shifts in some tetracyclic norbornyl systems, where the repulsion between groups separated by four or five bonds is so severe that the compressed proton appears uncommonly downfield by 3.1-3.5 ppm, but also, the uncompressed proton moves compensatingly upfield by 0.8-0.9 ppm (. Winstein S.P., Carter P., Anet F.A.L., and Bourn A.J.R. J. Am. Chem. Soc. 95 (1973) 8005 )
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J. Am. Chem. Soc.
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Winstein, S.P.1
Carter, P.2
Anet, F.A.L.3
Bourn, A.J.R.4
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For example, the chemical shift difference within the 4′,9′-H methylene in the case of 2-adamantanol or 2-t-Bu-adamantane is only ∼0.10 ppm; in these cases axial -OH or -t-Bu groups adopt an equatorial position with respect to the 1′-2′-3′-4′-5′-9′ cyclohexane ring (see Scheme 1, A = H, B = OH or t-Bu).
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Stereodynamics of Cyclohexane and Substituted Cyclohexanes. Substituent A Values
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Juaristi E. (Ed), VCH, New York
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Bushweller C.H. Stereodynamics of Cyclohexane and Substituted Cyclohexanes. Substituent A Values. In: Juaristi E. (Ed). Conformational Behaviour of Six-Membered Rings (1995), VCH, New York 25
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Conformational Behaviour of Six-Membered Rings
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1H NMR spectra of compounds 1-19 was striking; this high spectrum resolution is important for the liquid-state NMR measurements focusing on how suitable reporter adamantane derivatives contact with the transmembrane portion of the influenza A M2 protein receptor embedded in lipid bilayers (see, for example, Ref. 12a and also: )
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1H NMR spectra of compounds 1-19 was striking; this high spectrum resolution is important for the liquid-state NMR measurements focusing on how suitable reporter adamantane derivatives contact with the transmembrane portion of the influenza A M2 protein receptor embedded in lipid bilayers (see, for example, Ref. 12a and also:. Wang J., Schnell J.R., and Chou J.J. Biochem. Biophys. Res. Commun. 324 (2004) 212 )
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Wang, J.1
Schnell, J.R.2
Chou, J.J.3
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