E. Bahman Jahromi and A. Mehranpour
Vol 000
(2 H, d, J 6.8Hz), 8.58 (1H, d, J 2.4 Hz), 8.97 (1 H, d, J
2.4Hz), 9.32 (2 H, d, J 6.8 Hz); δC (100 MHz, d6-DMSO)
30.0, 37.1, 99.3, 104.8, 125.1, 125.5, 126.2, 144.6, 147.2,
147.9, 157.3, 159.3, 172.3; UV: λmax (DMSO)/nm = 363;
EI-MS (70ev): m/z =279 [M+]; Anal. Calcd for
(C17H19N4)(ClO4): C, 53.89; H, 5.01; N, 14.73. Found: C,
53.11; H, 4.87; N, 14.12.
1-(7-Amino-1,8-naphthyridin-3-yl)quinolinium perchlorate
[2b]. Dark brown powder; yield 68%; mp > 400°C; IR
(KBr), (cmÀ1): 3356, 3204, 1599, 1096; δH (400MHz,
d6-DMSO) 7.24 (1 H, d, J 2 Hz), 7.50 (2 H, s, NH2),7.88
(1 H, d, J 8.8Hz), 8.19 (1 H, t, J 7.6 Hz), 8.38 (1H, t, J
7.6Hz), 8.47 (1 H, d, J 8 Hz), 8.61 (1 H, d, J 8Hz), 8.71
(1 H, d, J 2.4Hz), 8.77 (1H, d, J 6.8 Hz), 9.12 (1 H, d, J
2.4Hz), 9.16 (1 H, d, J 6.8 Hz), 10.48 (1 H, d, J 8Hz); δC
(100 MHz, d6-DMSO) 121.1, 126.2, 127.8, 127.9, 130.3,
131.5, 132.0, 132.9, 135.4, 135.8, 137.4, 138.0, 138.4,
145.7, 150.5, 150.8, 153.0; UV: λmax (DMSO)/nm = 307;
EI-MS (70ev): m/z =273 [M+]; Anal. Calcd for
(C17H13N4)(ClO4): C, 54.78; H, 3.48; N, 15.02. Found:
C, 53.49; H, 3.24; N, 15.60.
(DMSO)/nm = 315; EI-MS (70ev): m/z = 271 [M+]; Anal.
Calcd for (C18H13N3): C, 79.68; H, 4.79; N, 15.48.
Found: C, 79.02; H, 4.37; N, 14.98.
2-(7-Amino-1,8-naphthyridin-3-yl)isoquinolinium perchlorate
[2f]. Brown powder; yield 58%; mp > 400°C; IR (KBr),
(cmÀ1): 3451, 3355, 1630, 1086; δH (400MHz,
d6ÀDMSO) 7.03 (1 H, d, J 9.1 Hz), 7.39 (2 H, s, NH2),
8.14–8.20 (2H, m), 8.37 (1H, t, J 8 Hz), 8.47 (1 H, d, J
8 Hz), 8.61 (1 H, d, J 6.3 Hz), 8.72 (1 H, d, J 1.8 Hz), 8.78
(1 H, d, J 7.7 Hz), 9.14 (1 H, d, J 6.3 Hz), 9.19 (1H, d, J
1.8 Hz), 10.46 (1 H, s); δC (100 MHz, d6-DMSO) 115.9,
116.0, 126.2, 127.81, 127.84, 131.5, 132.0, 132.9, 133.4,
135.5, 137.5, 138.1, 138.5, 147.5, 150.7, 157.7, 162.6;
UV: λmax (DMSO)/nm= 369; EI-MS (70ev): m/z= 273
[M+]; Anal. Calcd for (C17H13N4)(ClO4): C, 54.78; H,
3.48; N, 15.02. Found: C, 54.11; H, 3.27; N, 15.60.
6-Bromo-1,8-naphthyridin-2-amine [2 g].
Dark orange
powder; yield 62%; mp = 210°C; IR (KBr), (cmÀ1):
3336, 3193, 1624, 1094; δH (400 MHz, d6-DMSO) 7.11
(d, J 8.8 Hz, 1H), 7.57 (s, 2 H, NH2), 7.86 (d, J 8.8 Hz,
1 H), 8.59 (d, J 4.4 Hz, 1 H), 9.03 (d, J 4.4 Hz, 1 H); δC
(100 MHz, d6-DMSO) 115.2, 116.4, 136.4, 139.3, 140.3,
152.4, 159.6, 161.2; UV: λmax (DMSO)/nm = 361; EI-MS
(70ev): m/z= 224 [M]; Anal. Calcd for (C18H6BrN3): C,
42.88; H, 2.70; N, 18.75. Found: C, 43.01; H, 2.92; N,
18.81.
1-(7-Amino-1,8-naphthyridin-3-yl)pyridinium perchlorate
[2c].
Orange powder; yield 72%; mp >400°C; IR
(KBr), (cmÀ1): 3415, 3065, 1637, 1089; δH (400MHz,
d6-DMSO) 7.19 (1H, d, J 8.8 Hz), 7.77 (2 H, s, NH2),
7.82 (1H, d, J 8.8 Hz), 8.34 (2 H, t, J 7.2 Hz), 8.61 (1 H,
d, J 1.8Hz), 8.81 (1 H, t, J 8 Hz), 8.98 (1 H, d, J 2.8 Hz),
9.42 (2 H, dd, J1 6.8 Hz, J2 1.2 Hz); δC (100 MHz, d6-
DMSO) 105.7, 119.1, 121.1, 128.6, 130.4, 131.9, 132.7,
145.1, 145.3, 146.6, 150.7, 152.8; UV: λmax (DMSO)/
nm = 366; EI-MS(70ev): m/z= 222 [M+]; Anal. Calcd for
(C14H12N3)(ClO4): C, 52.26; H, 3.73; N, 13.05. Found:
C, 51.94; H, 3.25; N, 14.20.
Acknowledgments. Financial support of this work by the Research
Council of the Persian Gulf University is gratefully acknowledged.
REFERENCES AND NOTES
1-(7-Amino-1,8-naphthyridin-3-yl)-4-benzylpyridinium
[1] Bouzard, D.; DiCesare, P.; Essiz, M.; Jacquet, J. P.;
Ledoussal, B.; Remuzon, P.; Kessler, R. E.; Fung Tome, J. J Med Chem
1992, 35, 518.
[2] Rao, G. R.; Mogilaiah, K.; Sreenivasulu, B. Indian J Chem
1996, 35B, 339.
[3] Ferrarini, P. L.; Manera, C.; Mori, C.; Badawneh, M.;
Saccomanni, G. Farmaco 1998, 53, 741.
[4] Zhang, S. X.; Bastow, K. F.; Tachibana, Y.; Kuo, S. C.;
Hamel, E.; Mauger, A.; Narayanan, V. L.; Lee, K. H. J Med Chem
1999, 42, 4081.
[5] Kuroda, T.; Suzuki, F.; Tamura, T.; Ohmori, K.; Hosoe, H. J
Med Chem 1992, 35, 1130.
[6] Ferrarini, P. L.; Badawneh, M.; Franconi, F.; Manera, C.;
Miceli, M.; Mori, C.; Saccomanni, G. Farmaco 2001, 56, 311.
[7] Santilli, A.; Scotese, A. C.; Bauer, R. F.; Bell, S. C. J Med
Chem 1987, 30, 2270.
[8] Kuo, S. C.; Tsai, S. Y.; Li, H. T.; Wu, C. H.; Ishii, K.;
Nakamura, H. Chem Pharm Bull 1988, 36, 4403.
[9] Ferrarini, P. L.; Mori, C.; Tellini, N. Farmaco 1990, 45, 385.
[10] DaSettimo, A.; Primofiore, G.; DaSettimo, F.; Simorini, F.;
Barili, P. L.; Senatore, G.; Martini, C.; Lucacchini, A. Drug Des Discov
1994, 11, 307.
perchlorate [2d].
Dark brown powder; yield 70%;
mp >400°C; IR (KBr), (cmÀ1): 3363, 3187, 2923, 1641,
1094; δH (400 MHz, d6-DMSO) 4.41 (2 H, s, CH2), 7.03
(1 H, d, J 9.1Hz), 7.26–7.56 (5 H, m), 7.70 (2 H, s, NH2),
8.05–8.17 (2 H, m), 8.20 (1 H, d, J 9.1 Hz), 8.43 (1 H, d, J
1.8Hz), 8.49 (1H, d, J 1.8 Hz), 8.96 (2 H, d, J 6.8 Hz); δC
(100 MHz, d6-DMSO) 50.0, 117.3, 117.5, 117.8, 118.4,
118.5, 120.1, 120.8, 122.1, 122.4, 122.6, 124.9, 126.0,
146.2, 147.9, 155.0; UV: λmax (DMSO)/nm = 440; EI-MS
(70ev): m/z = 313 [M+]; Anal. Calcd for (C20H17N4)
(ClO4): C, 58.18; H, 4.11; N, 13.56. Found: C, 57.85; H,
4.46; N, 13.92.
6-Naphthalen-1-yl-1,8-naphthyridin-2-amine [2e]. Olivaceous
powder; yield 65%; mp = 270°C; IR (KBr), (cmÀ1): 3385,
3052, 1588, 1109; δH (400 MHz, d6-DMSO) 7.48 (1 H, d, J
9.1 Hz), 7.69 (2 H, s, NH2), 7.49–7.69 (7 H, m), 7.80 (1 H,
d, J 9.1 Hz), 7.98 (1 H, d, J 2.1 Hz), 8.06 (1 H, d, J 2.1 Hz);
δC (100 MHz, d6-DMSO) 102.3, 124.8, 124.9, 125.0,
125.8, 126.1, 127.2, 128.1, 129.1, 129.9, 130.3, 130.9,
133.2, 134.1, 140.1, 140.2, 141.1, 164.3; UV: λmax
[11] Herzig, S.; Heber, D.; Mescheder, A.; Reifenstein-Herzig, U.;
Thormann, T.; Verborg, M.; Mohr, K. Arzneim Forsch 1994, 44, 937.
[12] Ferrarini, P. L.; Mori, C.; Badawneh, M.; Calderone, V.;
Greco, R.; Manera, C.; Martinelli, A.; Nieri, P.; Saccomauni, G. Eur J
Med Chem 2000, 35, 815.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet