M. A. Loza-Mejía et al. / Bioorg. Med. Chem. 17 (2009) 3266–3277
3275
1H NMR (CDCl3, d): 1.02 (t, J = 7.2 Hz, 6H) 2-CH3; 2.55 (q, J = 7.2 Hz,
4H) CH2; 2.68 (t, J = 6.9 Hz, 2H) CH2; 3.48 (q, J = 6.9 Hz, 2H) NHCH2;
6.44 (br, 1H) -NH-; 7.00 (s, 1H) –NHAr; 7.04 (d, J = 8.1 Hz, 1H) H-60;
7.08 (s, 1H) H-20; 7.18 (d, J = 8.1 Hz, 1H) H-4; 07.26 (t, J = 8.1, 1H) H-
50; 7.37 (ddd; J = 8.7, 6.9, 1.2 Hz; 1H) H-7; 7.60 (ddd; J = 8.7, 6.9,
1.5 Hz; 1H) H-6; 7.67 (d, J = 8.7 Hz, 1H) H-5; 8.03 (d, J = 8.7 Hz,
1H) H-8; MS (FAB, m/z): 417 (M++1, 100%) Anal. Calcd for
C23H24N6S: C, 66.32; H, 5.81; N, 20.18; S, 7.70. Found: C, 66.17;
H, 6.00; N, 20.96; S, 7.51.
7.4.6. 9-[[(4-Methoxy)phenyl]amino]-2-[2-(N,N-diethylamino)]
ethylaminothiazolo[5,4-b]quinoline (10f)
Yellow solid; (65%); mp 110–112 °C. IR (KBr, cmꢁ1) 3179 (NH)
2966, 2827, (CH); 1599, 1563, 1508, 1495, 1469 (aromatic). 1236
(OCH3); 1H NMR (DMSO-d6, d): 0.88 (t, J = 7.2 Hz, 6H) 2-CH3; 2.41
(q, J = 7.2 Hz, 4H) CH2; 2.45 (t, J = 6.9 Hz, 2H) CH2; 3.23 (q,
J = 6.9 Hz, 2H) NHCH2; 3.68 (s, 3H) OCH3; 6.80 (m, 4H) H-2’, H-60,
H-30, H-50; 7.36 (ddd, J = 8.7, 6.9, 0.9 Hz, 1H) H-7; 7.52 (ddd,
J = 8.7, 6.9, 0.9 Hz, 1H) H-6; 7.79 (dd, J = 8.7, 0.9 Hz, 1H) H-5;
8.06 (dd, J = 8.7, 0.9 Hz, 1H) H-8; 8.13 (br, t, J = 6.9, 1H) –NH–;
8.29 (s, 1H) –NHAr–; MS (EI, m/z): 421 (M+, 15%), 322 (M-99,
80%), 86 (M-335, 100%) Anal. Calcd for C23H27N5OS: C, 65.53; H,
6.46; N, 16.61; S, 7.61. Found: C, 65.66; H, 6.49; N, 16.59; S, 7.47.
7.4.2. 9-[[(3-Chloro)phenyl]amino]-2-[2-(N,N-diethylamino)]
ethylaminothiazolo[5,4-b]quinoline (10b)
Yellow solid; (70%); mp 109–110 °C. IR (KBr, cmꢁ1) 3411
(NH), 2966, 2919, 2849 (CH); 1549, 1561, 1475 (aromatic); 1H
NMR (DMSO-d6, d): 1.10 (t, J = 7.2 Hz, 6H) 2-CH3; 2.97 (q,
J = 7.2 Hz, 4H) CH2; 3.10 (t, J = 6.9 Hz, 2H) CH2; 3.59 (q,
J = 6.9 Hz, 2H) NHCH2; 6.78 (d, J = 8.1 Hz, 1H) H-60; 6.90 (d,
J = 8.1 Hz, 1H) H-40; 7.20 (t, J = 8.1, 1H) H-50; 7.30 (s, 1H) H-20;
7.51 (ddd; J = 8.7, 6.9, 1.2 Hz, 1H) H-7; 7.64 (ddd, J = 8.7, 6.9,
1.5 Hz, 1H) H-6; 7.90 (d, J = 8.7 Hz, 1H) H-5; 8.22 (d, J = 8.7 Hz,
1H) H-8; 8.97 (br, t, J = 6.9, 1H) –NH–; 9.22 (s, 1H) –NHAr–;
MS (FAB, m/z): 426 (M++1, 40%), 86 (M-339, 100%) Anal. Calcd
for C22H24ClN5S: C, 62.03; H, 5.68; N, 20.69; S, 7.49. Found: C,
62.17; H, 5.81; N, 20.52; S, 7.35.
7.4.7. 9-(Phenylamino)-2-[3-(N,N-diethylamino)]propylamino-
thiazolo[5,4-b]quinoline (11a)
Yellow solid; 62 mg (59%); mp 72–75 °C. IR (KBr, cmꢁ1) 3233,
1562, 1493 (–NH–); 2967,2818 (CH); 1597 (aromatic). 1H NMR
(DMSO-d6, d): 0.9 (t, J = 7.2 Hz, 6H) 2-CH3; 1.6 (q, J = 7.0 Hz, 2H) –
CH2–; 2.4 (m, 6H) 3-CH2–; 3.2 (sa, 2H) –CH2–; 6.8 (d, J = 7.2 Hz,
3H) H-20, H-40, H-6’; 7.1 (ddd, J = 8.4,6.9,1.8 Hz, 2H) H-30, H-50;
7.4 (ddd, J = 8.4,6.9,1.5 Hz, 1H) H-7; 7.5 (ddd, J = 8.4,6.9,1.5 Hz,
1H) H-6; 7.9 (dd, J = 8.7,0.9 Hz, 1H) H-5; 8.0 (dd, J = 8.7,0.9 Hz,
1H) H-8; 8.3 (t, J = 5.4 Hz, 1H) –NH–; 8.5(s, 1H) –NH– MS (EI, m/
z) 405 (M+ 100%); 376 (M+-29, 15%); 319 (M+-89, 56%); 306 (M+-
99, 53%); Anal. Calcd for C23H27N5S: C, 68.11; H, 6.71; N, 17.27;
S, 7.91. Found: C, 68.15; H, 6.67; N, 17.31; S, 7.87.
7.4.3. 9-[[(3-Methoxy)phenyl]amino]-2-[2-(N,N-diethylamino)]
ethylaminothiazolo[5,4-b]quinoline (10c)
Brownish solid; (50%); mp 118–120 °C. IR (KBr, cmꢁ1): 3120
(NH), 3053, 2966 2850 (CH), 1595, 1571, 1543, 1503, 1476, (aro-
matic), 1H NMR (DMSO-d6, d): 0.88 (t, J = 7.2 Hz, 6H) 2-CH3; 2.41
(q, J = 7.2 Hz, 4H) CH2; 2.45 (t, J = 6.9 Hz, 2H) CH2; 3.23 (q,
J = 6.9 Hz, 2H) NHCH2; 6.74 (m, 3H) H-20, H-40, H-60; 7.25 (t,
J = 8.7 Hz) H-50; 7.60 (ddd, J = 8.4, 6.6, 1.2 Hz) H-7; 7.84 (ddd,
J = 8.7, 6.6, 1.2 Hz) H-6; 7.97 (dd, J = 8.7, 0.9 Hz, 1H) H-5; 8.53 (d,
J = 8.4 Hz) H-8; 8.13 (br, t, J = 6.9, 1H) –NH–; 8.29 (s, 1H) –NHAr–
; MS (EI, m/z): 421 (M+, 15%), 322 (M-99, 80%), 86 (M-335, 100%)
Anal. Calcd for C23H27N5OS: C, 65.53; H, 6.46; N, 16.61; S, 7.61.
Found: C, 65.41; H, 6.52; N, 16.67; S, 7.76.
7.4.8. 9-[[(3-Cyano)phenyl]amino]-2-[3-(N,N-diethylamino)]
propylaminothiazolo[5,4-b]quinoline (11b)
Yellow solid; 68 mg (57%); mp 73–76 °C. IR (KBr, cmꢁ1) 3209 (–
NH–); 2960, 2815 (CH), 2277 (CN); 1599, 1562,1494 (aromatic); 1H
NMR (DMSO-d6, d): 0.9 (t, J = 7.2 Hz, 3H) 2-CH3; 1.6 (q, J = 7.2 Hz;
2H) –CH2–; 2.4 (m, 6H) 3-CH2–; 3.2 (q, J = 7.2 Hz, 2H) –CH2–; 7.1
(d, J = 7.5 Hz, 2H) H-20, H-60; 7.2 (d, J = 7.5 Hz, 1H) H-40; 7.3 (ddd,
J = 8.4, 7.8, 0.9 Hz, 1H) H-50; 7.5 (ddd, J = 8.1,6.9,1.2 Hz, 1H) H-7;
7.6 (ddd, J = 8.4,6.9,1.2 Hz, 1H) H-6; 7.9 (d, J = 7.5 Hz, 1H) H-5;
8.1 (d, J = 7.8 Hz, 1H) H-8; 8.5 (br) –NH–; 9.0 (br) –NH– MS (EI,
m/z) 430 (M+ 100%); 401 (M+-29, 12%); 344(M+-86, 30%); 330
(M+-100, 27%). Anal. Calcd for C24H26N6S: C, 66.95; H, 6.09; N,
19.52; S, 7.45. Found: C, 66.74; H, 6.39; N, 19.33; S, 7.54.
7.4.4. 9-[[(4-Cyano)phenyl]amino]-2-[2-(N,N-diethylamino)]
ethylaminothiazolo[5,4-b]quinoline (10d)
Pale yellow solid; (61%); mp 114–115 °C. IR (KBr, cmꢁ1) 3320
(NH); 2967, (CH) 2216 (CN), 1602, 1580, 1560, 1511 (aromatic);
1H NMR (DMSO-d6, d):1.10 (t, J = 7.2 Hz, 6H) 2-CH3; 2.97 (q,
J = 7.2 Hz, 4H) CH2; 3.10 (t, J = 6.9 Hz, 2H) CH2; 3.59 (q, J = 6.9 Hz,
2H) NHCH2; 6.84 (d, J = 8.4 Hz, 2H) H-20, H-60; 7.55 (m, 3H) H-30,
H-50, H-7; 7.64 (ddd, J = 7.2, 6.9, 1.2 Hz, 1H) H-6; 7.91 (d,
J = 7.8 Hz, 1H) H-5; 8.04 (d, J = 8.4 Hz, 1H) H-8; 8.50 (br, 1H) –
NH– 9.3 (s, 1H) –NH– MS (FAB, m/z) 430 (M++1, 50%) 86 (M-344,
100%) Anal. Calcd for C23H24N6S: C, 66.32; H, 5.81; N, 20.18; S,
7.70. Found: C, 66.47; H, 5.93; N, 20.10; S, 7.50.
7.4.9. 9-[[(3-Chloro)phenyl]amino]-2-[3-(N,N-diethylamino)]
propylaminothiazolo[5,4-b]quinoline (11c)
Yellow solid; 45 mg (55.0%); mp 55–58 °C. IR (KBr, cmꢁ1) 2966,
1375 (–CH); 1594, 1561, 1497 (aromatic); 1H NMR (DMSO-d6, d):
0.9 (t, J = 7.2 Hz, 6H) 3-CH3; 1.6 (q, J = 6.9 Hz, 2H) –CH2–; 2.4 (m,
6H) 3-CH2–; 3.3 (c, J = 6.6 Hz, 2H) –CH2–; 6.7 (d, J = 9.0 Hz, 1H)
H-60; 6.8 (d, J = 6.3 Hz, 2H) H-20, H-40; 7.1 (t, J = 8.1 Hz, 1H) H-50;
7.5 (t, J = 7.5 Hz, 1H) H-7; 7.6 (t, J = 7.5 Hz, 1H) H-6; 7.9 (t,
J = 8.4 Hz, 1H) H-5; 8.1 (d, J = 8.4 Hz, 1H) H-8; 8.4 (br) –NH–; 8.8
(s, 1H) –NH– MS (EI, m/z) 438 (M+, 100%); 410 (M+-29, 8%); 353
(M+-57, 28%). Anal. Calcd for C23H26ClN5S: C, 62.78; H, 5.96; N,
15.92; S, 7.29. Found: C, 62.78; H, 5.85; N, 15.81; S, 7.29.
7.4.5. 9-[[(4-Chloro)phenyl]amino]-2-[2-(N,N-diethylamino)]
ethylaminothiazolo[5,4-b]quinoline (10e)
Yellow solid; (63%); mp 113–114 °C. IR (KBr, cmꢁ1) 3410 (NH),
2965, 2809, (CH); 1600, 1586, 1566 (aromatic); 1H NMR (DMSO-d6,
d): 1.08 (t, J = 7.2 Hz, 6H) 2-CH3; 2.94 (q, J = 7.2 Hz, 4H) CH2; 3.08 (t,
J = 6.9 Hz, 2H) CH2; 3.58 (q, J = 6.9 Hz, 2H) NHCH2; 6.82 (d,
J = 8.7 Hz, 2H) H-20, H-60; 7.21 (d, J = 8.7 Hz, 2H) H-30, H-50; 7.48
(ddd, J = 8.7, 6.9, 1.2 Hz, 1H) H-7; 7.60 (ddd, J = 8.7, 6.9, 1.5 Hz,
1H) H-6; 7.88 (d, J = 8.7 Hz, 1H) H-5; 8.16 (d, J = 8.7 Hz, 1H) H-8;
8.4 (br, t, J = 6.9, 1H) –NH–; 8.91 (s, 1H) –NHAr–; MS (FAB, m/z):
426 (M++1, 40%), 86 (M-339, 100%) Anal. Calcd for C22H24ClN5S:
C, 62.03; H, 5.68; N, 20.69; S, 7.49. Found: C, 62.21; H, 5.73; N,
20.64; S, 7.30.
7.4.10. 9-[[(4-Cyano)phenyl]amino]-2-[3-(N,N-diethylamino)]
propylaminothiazolo[5,4-b]quinoline (11d)
Yellow solid; 92 mg (71%); mp 75–78 °C IR (KBr, cmꢁ1) 3316 (R–
NH–R); 2960, 1466, 1378 (CH); 2217 (CN); 1603, 1561, 1512, 1466
(aromatic); 1H NMR (DMSO-d6, d):0.9 (t, J = 7.2 Hz, 6H) 2-CH3; 1.6
(q, J = 6.9 Hz, 2H) –CH2–; 2.4 (m, 6H) 3-CH2–; 3.2 (sa, 2H) –CH2–;
6.8 (d, J = 8.4 Hz, 2H) H-2’, H-60; 7.5 (d, J = 8.7 Hz, 3H) H-30, H-50,
H-7; 7.6 (ddd; J = 7.2, 6.9, 1.2 Hz, 1H) H-6; 7.9 (d, J = 7.8 Hz, 1H)
H-5; 8.0 (d, J = 8.4 Hz, 1H) H-8; 8.5 (br, 1H) –NH– 9.3 (s, 1H) –
NH– MS (EI, m/z) 430 (M+, 71%) 401 (M+-29, 9%) 344 (M+-57,