-
1
-
-
22844432580
-
-
For leading references to nicotinic pharmacophore studies see
-
A. A. Jensen, B. Frølund, T. Lijefors, P. Krogsgaard-Larsen, J. Med. Chem. 2005, 48, 4705-4745. For leading references to nicotinic pharmacophore studies see
-
(2005)
J. Med. Chem.
, vol.48
, pp. 4705-4745
-
-
Jensen, A.A.1
Frølund, B.2
Lijefors, T.3
Krogsgaard-Larsen, P.4
-
4
-
-
20844441945
-
-
J. W. Coe, P. R. Brooks, M. G. Vetelino, M. C. Wirtz, E. P. Arnold, J. Huang, S. B. Sands, T. I. Davis, L. A. Lebel, C. B. Fox, A. Shrikhande, J. H. Heym, E. Schaeffer, H. Rollema, Y. Lu, R. S. Mansbach, L. K. Chambers, C. C. Rovetti, D. W. Schulz, F. D. Tingley, B. T. O'Neill, J. Med. Chem. 2005, 48, 3474-3477
-
(2005)
J. Med. Chem.
, vol.48
, pp. 3474-3477
-
-
Coe, J.W.1
Brooks, P.R.2
Vetelino, M.G.3
Wirtz, M.C.4
Arnold, E.P.5
Huang, J.6
Sands, S.B.7
Davis, T.I.8
Lebel, L.A.9
Fox, C.B.10
Shrikhande, A.11
Heym, J.H.12
Schaeffer, E.13
Rollema, H.14
Lu, Y.15
Mansbach, R.S.16
Chambers, L.K.17
Rovetti, C.C.18
Schulz, D.W.19
Tingley, F.D.20
O'Neill, B.T.21
more..
-
5
-
-
77953233982
-
-
J. W. Coe, H. Rollema, B. T. O'Neill, Annu. Rep. Med. Chem. 2009, 44, 71-101.
-
(2009)
Annu. Rep. Med. Chem.
, vol.44
, pp. 71-101
-
-
Coe, J.W.1
Rollema, H.2
O'Neill, B.T.3
-
6
-
-
33747188593
-
-
Natural cytisine has also been used extensively within Eastern Europe for smoking cessation.
-
Natural cytisine has also been used extensively within Eastern Europe for smoking cessation., J. F. Etter, Arch. Intern. Med. 2006, 166, 1553-1559.
-
(2006)
Arch. Intern. Med.
, vol.166
, pp. 1553-1559
-
-
Etter, J.F.1
-
7
-
-
0034918683
-
-
P. Imming, P. Klaperski, M. T. Stubbs, G. Seitz, D. Gündisch, Eur. J. Med. Chem. 2001, 36, 375-388
-
(2001)
Eur. J. Med. Chem.
, vol.36
, pp. 375-388
-
-
Imming, P.1
Klaperski, P.2
Stubbs, M.T.3
Seitz, G.4
Gündisch, D.5
-
8
-
-
0034689851
-
-
E. Marrière, J. Rouden, V. Tadino, M.-C. Lasne, Org. Lett. 2000, 2, 1121-1124
-
(2000)
Org. Lett.
, vol.2
, pp. 1121-1124
-
-
Marrière, E.1
Rouden, J.2
Tadino, V.3
Lasne, M.-C.4
-
9
-
-
33646480887
-
-
S. K. Chellappan, Y. Xiao, W. Tueckmantel, K. J. Kellar, A. P. Kozikowski, J. Med. Chem. 2006, 49, 2673-2676
-
(2006)
J. Med. Chem.
, vol.49
, pp. 2673-2676
-
-
Chellappan, S.K.1
Xiao, Y.2
Tueckmantel, W.3
Kellar, K.J.4
Kozikowski, A.P.5
-
10
-
-
41149084769
-
-
A. P. Kozikowski, S. K. Chellappan, Y. Xiao, K. M. Bajjuri, H. Yuan, K. J. Kellar, P. A. Petukhov, ChemMedChem 2007, 2, 1157-1161
-
(2007)
ChemMedChem
, vol.2
, pp. 1157-1161
-
-
Kozikowski, A.P.1
Chellappan, S.K.2
Xiao, Y.3
Bajjuri, K.M.4
Yuan, H.5
Kellar, K.J.6
Petukhov, P.A.7
-
11
-
-
0345283018
-
-
A small number of C4-substituted cytisine derivatives have been reported; see Ref. [4c] and [8a].
-
G. Roger, B. Lagnel, J. Rouden, L. Besret, H. Valette, S. Demphel, J. Gopisetti, C. Coulon, M. Ottaviani, L. A. Wrenn, S. R. Letchworth, G. A. Bohme, J. Benavides, M.-C. Lasne, M. Bottlaender, F. Dollé, Bioorg. Med. Chem. 2003, 11, 5333-5343. A small number of C4-substituted cytisine derivatives have been reported; see Ref. [4c] and [8a].
-
(2003)
Bioorg. Med. Chem.
, vol.11
, pp. 5333-5343
-
-
Roger, G.1
Lagnel, B.2
Rouden, J.3
Besret, L.4
Valette, H.5
Demphel, S.6
Gopisetti, J.7
Coulon, C.8
Ottaviani, M.9
Wrenn, L.A.10
Letchworth, S.R.11
Bohme, G.A.12
Benavides, J.13
Lasne, M.-C.14
Bottlaender, M.15
Dollé, F.16
-
12
-
-
33750615072
-
-
N. Houllier, S. Gouault, M.-C. Lasne, J. Rouden, Tetrahedron 2006, 62, 11679-11686
-
(2006)
Tetrahedron
, vol.62
, pp. 11679-11686
-
-
Houllier, N.1
Gouault, S.2
Lasne, M.-C.3
Rouden, J.4
-
13
-
-
0037025264
-
-
J. Rouden, A. Ragot, S. Gouault, D. Cahard, J.-C. Plaquevent, M.-C. Lasne, Tetrahedron: Asymmetry 2002, 13, 1299-1305
-
(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 1299-1305
-
-
Rouden, J.1
Ragot, A.2
Gouault, S.3
Cahard, D.4
Plaquevent, J.-C.5
Lasne, M.-C.6
-
15
-
-
0037374126
-
-
C. Canu Boido, B. Tasso, V. Boido, F. Sparatore, Farmaco 2003, 58, 265-277.
-
(2003)
Farmaco
, vol.58
, pp. 265-277
-
-
Canu Boido, C.1
Tasso, B.2
Boido, V.3
Sparatore, F.4
-
17
-
-
0034727943
-
-
For the synthesis of C4-substituted derivatives see B. T. O'Neill, D. Yohannes, M. W. Bundesmann, E. P. Arnold, Org. Lett. 2000, 2, 4201-4204
-
(2000)
Org. Lett.
, vol.2
, pp. 4201-4204
-
-
O'Neill, B.T.1
Yohannes, D.2
Bundesmann, M.W.3
Arnold, E.P.4
-
18
-
-
79956089466
-
-
Ref. [4c]
-
Ref. [4c]
-
-
-
-
19
-
-
78149282046
-
-
P. Durkin, P. Magrone, S. Matthews. C. Dallanoce, T. Gallagher, Synlett 2010, 18, 2789-2791.
-
(2010)
Synlett
, vol.18
, pp. 2789-2791
-
-
Durkin, P.1
Magrone, P.2
Dallanoce, S.3
Matthews, C.4
Gallagher, T.5
-
20
-
-
41149113617
-
-
as well as Ref. [8c].
-
D. Yohannes, K. Procko, L. A. Lebel, C. B. Fox, B. T. O'Neill, Bioorg. Med. Chem. Lett. 2008, 18, 2316; as well as Ref. [8c].
-
(2008)
Bioorg. Med. Chem. Lett.
, vol.18
, pp. 2316
-
-
Yohannes, D.1
Procko, K.2
Lebel, L.A.3
Fox, C.B.4
O'Neill, B.T.5
-
21
-
-
61349183143
-
-
D. Yohannes, C. P. Hansen, S. R. Akireddy, T. A. Hauser, M. N. Kiser, N. J. Gurnon, C. S. Day, B. Bhatti, W. S. Caldwell, Org. Lett. 2008, 10, 5353-5356.
-
(2008)
Org. Lett.
, vol.10
, pp. 5353-5356
-
-
Yohannes, D.1
Hansen, C.P.2
Akireddy, S.R.3
Hauser, T.A.4
Kiser, M.N.5
Gurnon, N.J.6
Day, C.S.7
Bhatti, B.8
Caldwell, W.S.9
-
22
-
-
0035902187
-
-
A. B. Smit, N. I. Syed, D. Schaap, J. van Minnen, J. Klumperman, K. S. Kits, H. Lodder, R. C. van der Schors, R. van Elk, B. Sorgedrager, K. Brejc, T. K. Sixma, W. P. M. Geraerts, Nature 2001, 411, 261-268
-
(2001)
Nature
, vol.411
, pp. 261-268
-
-
Smit, A.B.1
Syed, N.I.2
Schaap, D.3
Van Minnen, J.4
Klumperman, J.5
Kits, K.S.6
Lodder, H.7
Van Der Schors, R.C.8
Van Elk, R.9
Sorgedrager, B.10
Brejc, K.11
Sixma, T.K.12
Geraerts, W.P.M.13
-
23
-
-
0035902009
-
-
K. Brejc, W. J. van Dijk, R. V. Klaassen, M. Schuurmans, J. van der Oost, A. B. Smit, T. K. Sixma, Nature 2001, 411, 269-276
-
(2001)
Nature
, vol.411
, pp. 269-276
-
-
Brejc, K.1
Van Dijk, W.J.2
Klaassen, R.V.3
Schuurmans, M.4
Van Der Oost, J.5
Smit, A.B.6
Sixma, T.K.7
-
24
-
-
1842475289
-
-
P. H. N. Celie, S. E. van Rossum-Fikkert, W. J. van Dijk, K. Brejc, A. B. Smit, T. K. Sixma, Neuron 2004, 41, 907-914
-
(2004)
Neuron
, vol.41
, pp. 907-914
-
-
Celie, P.H.N.1
Van Rossum-Fikkert, S.E.2
Van Dijk, W.J.3
Brejc, K.4
Smit, A.B.5
Sixma, T.K.6
-
25
-
-
18444411922
-
-
Y. Bourne, T. T. Talley, S. B. Hansen, P. Taylor, P. Marchot, EMBO J. 2005, 24, 1512-1522
-
(2005)
EMBO J.
, vol.24
, pp. 1512-1522
-
-
Bourne, Y.1
Talley, T.T.2
Hansen, S.B.3
Taylor, P.4
Marchot, P.5
-
26
-
-
27144473613
-
-
S. B. Hansen, G. Sulzenbacher, T. Huxford, P. Marchot, P. Taylor, Y. Bourne, EMBO J. 2005, 24, 3635-3646.
-
(2005)
EMBO J.
, vol.24
, pp. 3635-3646
-
-
Hansen, S.B.1
Sulzenbacher, G.2
Huxford, T.3
Marchot, P.4
Taylor, P.5
Bourne, Y.6
-
27
-
-
34547520128
-
-
C. D. Dellisanti, Y. Yao, J. C. Stroud, Z. Z. Wang, L. Chen, Nat. Neurosci. 2007, 10, 953-962.
-
(2007)
Nat. Neurosci.
, vol.10
, pp. 953-962
-
-
Dellisanti, C.D.1
Yao, Y.2
Stroud, J.C.3
Wang, Z.Z.4
Chen, L.5
-
28
-
-
77954219703
-
-
J. A. Abin-Carriquiry, M. P. Zunini, B. K. Cassels, S. Wonnacott, F. Dajas, Bioorg. Med. Chem. Lett. 2010, 20, 3683-3687.
-
(2010)
Bioorg. Med. Chem. Lett.
, vol.20
, pp. 3683-3687
-
-
Abin-Carriquiry, J.A.1
Zunini, M.P.2
Cassels, B.K.3
Wonnacott, S.4
Dajas, F.5
-
30
-
-
33746279633
-
-
Angew. Chem. Int. Ed. 2006, 45, 2419-2423.
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 2419-2423
-
-
-
31
-
-
77952998618
-
-
Key step of our earlier method was the intramolecular 1,6-addition of a lactam enolate to a 2-pyridone (22 a → 23 a). This was unsuccessful for 22 b → 23 b and 22 c → 23 c where evidence was obtained for addition of the HMDS anion to the heterocycle.
-
T. Gallagher, I. Derrick, P. M. Durkin, C. A. Haseler, C. Hirschhäuser, P. Magrone, J. Org. Chem. 2010, 75, 3766-3774. Key step of our earlier method was the intramolecular 1,6-addition of a lactam enolate to a 2-pyridone (22 a → 23 a). This was unsuccessful for 22 b → 23 b and 22 c → 23 c where evidence was obtained for addition of the HMDS anion to the heterocycle.
-
(2010)
J. Org. Chem.
, vol.75
, pp. 3766-3774
-
-
Gallagher, T.1
Derrick, I.2
Durkin, P.M.3
Haseler, C.A.4
Hirschhäuser, C.5
Magrone, P.6
-
32
-
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77953558609
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All compounds described here are racemic. The synthesis of (R)- 5 a and nonnatural (+)-cytisine has been reported; see Ref. [14] and also.
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All compounds described here are racemic. The synthesis of (R)- 5 a and nonnatural (+)-cytisine has been reported; see Ref. [14] and also:, M. H. Kim, Y. Park, B. S. Jeong, H. G. Park, S. S. Jew, Org. Lett. 2010, 12, 2826-2829.
-
(2010)
Org. Lett.
, vol.12
, pp. 2826-2829
-
-
Kim, M.H.1
Park, Y.2
Jeong, B.S.3
Park, H.G.4
Jew, S.S.5
-
33
-
-
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-
A related sequence involving configurationally stable cis-piperidines has been described, see Ref. [8a] and.
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A related sequence involving configurationally stable cis-piperidines has been described, see Ref. [8a] and, T. Honda, R. Takahashi, H. Namiki, J. Org. Chem. 2005, 70, 499-504.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 499-504
-
-
Honda, T.1
Takahashi, R.2
Namiki, H.3
-
34
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79956148531
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For conditions used see the Supporting Information. Selective thionation of the lactam C=O of 19 using Lawesson's reagent failed (see the Supporting Information).
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For conditions used see the Supporting Information. Selective thionation of the lactam C=O of 19 using Lawesson's reagent failed (see the Supporting Information).
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35
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79956105089
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2O caused degradation
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2O caused degradation.
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36
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79956122348
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50 of 85 n M (cf. (-)-cytisine 7.7 n M; A. Kennett, S. Wonnacott, C. Hirschhäuser, C. A. Haseler, T. Gallagher, unpublished results). Coe et al. have reported that varenicline is three-fold more potent than cytisine at α4β2 in rat cortex; see Ref. [2a]
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50 of 85 n M (cf. (-)-cytisine 7.7 n M; A. Kennett, S. Wonnacott, C. Hirschhäuser, C. A. Haseler, T. Gallagher, unpublished results). Coe et al. have reported that varenicline is three-fold more potent than cytisine at α4β2 in rat cortex; see Ref. [2a].
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