1080
M. A. L. Blackie et al. / Bioorg. Med. Chem. Lett. 20 (2010) 1078–1080
3
3
d, JHH = 9), 7.40–7.37 (1H, m), 7.31–7.22 (4H, m), 6.52 (1H, d, JHH = 5), 4.42
(2H, s), 3.46 (2H, s), 2.24 (6 H, s); dC{H} (100 MHz) 152.3, 150.7 (CIV), 149.5 (CIV),
137.5 (CIV), 137.2 (CIV), 134.7 (CIV), 132.1, 130.1, 128.6, 128.1, 124.9, 122.3,
118.3 (CIV), 99.0, 62.7, 47.4, 45.1 (2C); IR (KBr) mmax 3426br m, 3212br m,
3065m, 3021m, 2968m, 2941m, 2858m, 2817m, 2790m, 2768m, 1662m,
1610m, 1575s, 1485m, 1449m, 1350m, 1326m, 1284m, 1237s, 1163m, 1147m,
1040w, 1014m, 967w, 901m, 882m, 840m, 811s, 771m, 746s, 645m, 590m,
541m; HRMS (EI) m/z 325.13380 [M+, C19H20N335Cl requires 325.13458].
Supplementary data
Supplementary data associated with this article can be found, in
References and notes
12. N-(2-((Dimethylamino)methyl)benzyl)quinolin-4-amine, 5: mp 133 °C
;
C19H21N3 requires C, 78.32; H, 7.26; N, 14.42. Found C, 78.38; H, 7.21; N,
1. World Health Report 2002.
3
14.45; dH (300 MHz, solvent CDCl3) 8.57 (1H, d JHH = 6 Hz), 8.14 (1H, br NH),
2. (a) De, D.; Krogstad, F. M.; Cogswell, F. B.; Krogstad, D. J. Am. J. Trop. Med. Hyg.
1996, 55, 579; (b) Ridley, R. G.; Hofheinz, W.; Matile, H.; Jaquet, C.; Dora, A.;
Masciadri, R.; Jolidon, S.; Richter, W. E.; Guenzi, A.; Girometta, M.-A.; Urwyler,
H.; Huber, W.; Thaithong, G.; Peters, W. Antimicrob. Agents Chemother. 1996, 40,
1846.
3. Biot, C.; Gloriam, G.; Maciejewski, L.; Brocard, J. S.; Domarle, O.; Blampain, G.;
Millet, P.; Georges, A. J.; Abessolo, H.; Dive, D.; Lebibi, J. J. Med. Chem. 1997, 40,
3715.
4. Dubar, F.; Khalife, J.; Brocard, J.; Dive, D.; Biot, C. Molecules 2008, 13, 2900.
5. Biot, C.; Chavain, N.; Dubar, F.; Pradines, B.; Trivelli, X.; Brocard, J.; Forfar, I.;
Dive, D. J. Organomet. Chem. 2009, 16, 845.
6. Biot, C.; Taramelli, D.; Forfar-Bares, I.; Maciejewski, L.; Boyce, M.; Nowogrocki,
G.; Brocard, J. S.; Basilico, N.; Olliaro, P.; Egan, T. J. Mol. Pharmacol. 2005, 2, 185.
7. Beagley, P.; Blackie, M. A. L.; Chibale, K.; Clarkson, C.; Meijboom, R.; Moss, J. R.;
Smith, P. J.; Su, H. Dalton Trans. 2003, 3046.
3
3
4
7.95 (1H, d JHH = 8 Hz), 7.69 (1H, dd, JHH = 8 Hz, JHH = 1 Hz), 7.52–7.60 (1H,
m), 7.39–7.42 (1H, m), 7.20–7.36 (4H, m), 6.48 (1H, d 3JHH = 6 Hz), 4.46 (2H, s),
3.48 (2H, s), 2.26 (6H, s); dC{H} (75 MHz, solvent CDCl3) 151.1, 150.5, 148.7,
137.6 (CIV), 137.2, 131.8, 130.5, 129.6, 128.7, 124.0, 120.4, 119.6, 98.5 (CIV),
62.5, 41.2, 44.9 (2C); m/z (FAB) 292 (M+H, 100), 290 (15), 247 (17), 148 (7), 129
(10).
13. Levi, E. M.; Hauser, C. R. J. Org. Chem. 1969, 34, 2482.
14. Barnish, I. T.; Hauser, C. R. J. Org. Chem. 1968, 33, 1372.
15. Hine, J.; Li, W.-S. J. Org. Chem. 1975, 40, 289.
16. N-(7-Chloroquinolin-4-yl)-N0-(2-dimethylamino-methylbenzyl)-ethane-1,2-
diamine, 6: 1.88 g, 60%; C21H25N4Cl requires C, 68.37; H, 6.83; N, 15.19. Found
3
C, 68.05; H, 6.75; N, 12.10; dH (400 MHz) 8.53 (1H, d, JHH = 5), 7.95 (1H, d,
3
4
3
4JHH = 2), 7.76 (1H, d, JHH = 9), 7.38 (1H, dd, JHH = 2 and JHH = 9), 7.33–7.18
(4H, m), 6.41 (1H, d, 3JHH = 5), 3.85 (2H, s), 3.43 (2H, s), 3.34–3.29 (2H, m), 3.00–
2.95 (2H, m), 2.11 (6H, s) dC{H} (100 MHz) 152.0, 150.5 (CIV), 149.2 (CIV), 138.0
(CIV), 137.5 (CIV), 131.1 (2C), 130.8 (2C), 128.7, 127.8, 125.3, 121.2 (CIV), 99.2,
62.5, 51.6, 45.0, 44.7 (2C), 40.2; IR (NaCl neat) mmax 3265m, 3054m, 2944m,
2858m, 2820m, 1611s, 1582vs, 1535s, 1450s, 1428m, 1367s, 1331s, 1265s,
1140m, 1081m, 1041w, 1017m, 878m, 843m, 808m, 738s, 703m; HRMS (EI) m/
z 368.17829 [M+, C21H25N435Cl requires 368.17677].
8. Kaschula, C. H.; Egan, T. J.; Hunter, R.; Basilico, N.; Parapini, S.; Taramelli, D.;
Pasini, E.; Monti, D. J. Med. Chem. 2002, 45, 3531.
9. Blackie, M. A. L.; Beagley, P.; Croft, S. L.; Kendrick, H.; Moss, J. R.; Chibale, K.
Bioorg. Med. Chem. 2007, 15, 6510.
10. Funke, A.; Bovet, D.; Montezin, G. Ann. Inst. Pasteur 1946, 72, 264.
11. 7-Chloro-N-(2-((dimethylamino)methyl)benzyl)-quinolin-4-amine 3: C19H20
-
17. Chibale, K.; Moss, J. R.; Blackie, M.; van Schalkwyk, D.; Smith, P. J. Tetrahedron
Lett. 2000, 41, 6231.
ClN3 requires C, 70.04; H, 6.19; N, 12.90. Found. C, 69.98; H, 6.25; N, 12.76; dH
(400 MHz) 8.53 (1H, d, 3JHH = 5), 8.31 (1H, br s), 7.90 (1H, d, 4JHH = 2), 7.62 (1H,