1H NMR (CDCl3, 300 MHz) δ: 2.68 (s, 3H, SCH3), 3.73 (t, J = 2.1 Hz, 2H, CH2), 3.86 (t, J = 2.1 Hz, 2H, CH2), 7.62–7.72 (m, 2H, H-6 and H-7), 8.11–8.59 (m, 2H, H-5 and H-8), 8.79 (s, 1H, H-2). CI MS m/z (rel. intensity) 294 (M + H+, 100), 258 (40). Anal. Calc. for C14H12ClNS2: C 57.23, H 4.12, N 4.77. Found: C 57.44, H 4.05, N 4.80. 4-(4-Chloro-2-butynylseleno)-3-methylthioquinoline (8) Yield 56%. Mp: 67–68°C. 1H NMR (CDCl3, 300 MHz) δ: 2.67 (s, 3H, SCH3), 3.62 (t, J = 2.4 Hz, 2H, CH2), 3.88 (t, J = 2.4 Hz, 2H, CH2), 7.61–7.70 (m, 2H, H-6 and H-7), 8.14–8.52 (m, 2H, H-5 and H-8),
8.76 (s, 1H, H-2). CI MS m/z (rel. intensity) 342 (M + H+, 100), 306 (35). Anal. Calc. for C14H12ClNSSe: C 49.35, H 3.55, N 4.11. Found: C 49.47, H 3.38, N 4.20. 4-(4-Chloro-2-butynylthio)-3-(propargylthio)quinoline (9) Yield 63%. Mp: 109–110°C. RG7420 solubility dmso 1H NMR (CDCl3, 300 MHz) δ: 2.28 (t, J = 2.7 Hz, 1H, CH), 3.74 (t, J = 2,4 Hz, 2H, CH2), 3.84 (d, J = 2.7 Hz,
2H, CH2S), 3.88 (t, J = 2.4 Hz, 2H, CH2), 7.65–7.72 (m, 2H, H-6 and H-7), 8.10–8.59 (m, 2H, H-5 and H-8), 9.01 (s, 1H, H-2). CI MS m/z (rel. intensity) 318 (M + H+, 100), 282 (20), 232 (15). Anal. Calc. for C16H12ClNS2: C 60.46, H 3.81, N 4.41. Found: C 60.67, H 3.90, N 4.30. 4-(4-Chloro-2-butynylseleno)-3-(propargylthio)quinoline (10) Yield 77%. Mp: 92–93°C. 1H NMR (CDCl3, 300 MHz) δ: 2.28 (t, J = 2.7 Hz, 1H, CH), 3.63 (t, J = 2.4 Hz, 2H, CH2), 3.82 (d, J = 2.7 Hz, 2H, CH2S), 3.89 (t, J = 2.4 Hz, 2H, CH2), 7.66–7.72 (m, 2H, H-6 and H-7), 8.07–8.53 (m, 2H, H-5 and H-8), 8.99 (s, 1H, H-2). CI MS m/z (rel. intensity) 366 (M + H+, 100), 326 (20). Anal. Calc. selleck for C16H12ClNSSe: C 52.69, H 3.32, N 3.84. Found: C 52.77, H 3.40, N 3.68. 4-(4-Chloro-2-butynylthio)-3-(4-hydroxy-2-butynylthio)quinoline (11) Yield 58%. Mp: 103–104°C. 1H NMR (CDCl3, Megestrol Acetate 300 MHz) δ: 3.75 (t, J = 2.1 Hz, 2H, CH2), 3.87–3.89 (m, 4H, 2× CH2), 4.24 (t, J = 2.1 Hz, 2H, CH2), 7.66–7.74 (m, 2H, H-6 and H-7), 8.10–8.58 (m, 2H, H-5 and H-8), 9.02 (s, 1H, H-2). CI MS m/z (rel. intensity) 348 (M + H+, 40), 362 (55), 244 (100).
Anal. Calc. for C17H14ClNOS2: C 58.70, H 4.06, N 4.03.