Calc. for C17H17NO3S2: C 58.77, H 4.93,

N 4.03. Found: C 58.98, H 4.85, N 4.19. 4-(4-Cinnamoyloxy-2-butynylthio)-3-methylthioquinoline (23) Yield 91%. Mp: 82–83°C. 1H NMR (CDCl3, 300 MHz) δ: 2.68 (s, 3H, SCH3), 3.73 (t, J = 2.1 Hz, 2H, CH2), 4.57 (t, J = 2.1 Hz, 2H, CH2), 6.36 (d, J = 16.2 Hz, 1H, CH), 7.39–7.68 (m, 8H, CH and C6H5 and H-6 and H-7), 8.04–8.59 (m, 2H, H-5 and H-8), 8.80 (s, 1H, H-2). CI MS m/z (rel. intensity) 406 (M + H+, 100). Anal. Calc. for C23H19NO2S2: C 68.12, H 4.72, N 3.45. Found: C 68.32, H 4.56, N 3.48.

4-(4-Cinnamoyloxy-2-butynylseleno)-3-methylthioquinoline Selleck CP673451 AZD5582 cost (24) Yield 42%. Mp: 98–99°C. 1H NMR (CDCl3, 300 MHz) δ: 2.67 (s, 3H, SCH3), 3.63 (t, J = 2.1 Hz, 2H, CH2), 4.58 (t, J = 2.1 Hz, 2H, CH2), 6.37 (d, J = 15.9 Hz, 1H, CH), 7.39–7.69 (m, 8H, CH and C6H5 and H-6 and H-7), 8.02–8.53 (m, 2H, H-5 i H-8), 8.77 (s, 1H, H-2). CI MS m/z (rel. intensity) 453 (M + H+, 90), 256 (100). Anal. Calc. for C23H19NO2SSe: C 61.06, H 4.23, N 3.10. Found: C 60.81, H 4.12, N 3.18. 4-(4-Cinnamoyloxy-2-butynylthio)-3-(propargylthio)quinoline (25) Yield 80%. Mp: 102–103°C. 1H NMR (CDCl3, 300 MHz) δ: 2.27 (t, J = 2,7 Hz, 1H, CH), 3.75 (t, J = 2,4 Hz, 2H, CH2), 3.84 (d, J = 2.7 Hz, 2H, SCH2), 4.58 (t, J = 2.4 Hz, 2H, CH2), 6.36 (d, J = 15.9 Hz, 1H, CH), 7.39–7.69 (m, 8H, CH and C6H5 and H-6 and H-7), 8.07–8.60 (m, 2H, H-5 and H-8), 9.01 (s, 1H, H-2). CI MS m/z (rel. intensity) 430 (M + H+, 20), 232 (100). Anal. Calc. for C25H19NO2S2:

C 69.90, H 4.46, N 3.26. Found: C 70.12, H 4.52, N 3.38. Antiproliferative assay in vitro Cells The following established in vitro cancer cell lines were applied: SW707 (human colorectal adenocarcinoma), CCRF/CEM (human leukemia), T47D (human breast cancer), P388 LY294002 (mouse leukemia), and B16 (mouse melanoma). All lines were obtained from the American Type Culture Collection (Rockville, Maryland, USA) and maintained at the Cell Culture Collection of the Institute of Immunology and Experimental Therapy, Wroclaw, Poland. Twenty-four hours before addition of the tested agents, the cells were plated in 96-well plate (Sarstedt, USA) at a density of 104 cells per well in 100 μl of culture medium. The cells were cultured in the opti-MEM medium supplemented with 2 mM glutamine (Gibco, Warsaw, Poland), streptomycin (50 μg/ml), penicillin (50 U/ml) (both antibiotics from Polfa, Tarchomin, Poland), and 5% fetal calf serum (Gibco, Grand Island, USA). SRB assay The details of this technique were described by Mocetinostat cell line Skehan et al.