7-(4-((1-(4-Bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-
4-oxo-1,4-dihydroquinoline-3-carboxylic acid (29).
Brown powder; yield: 0.21 g (65%); m.p. 130.4 – 130.5 ; IR vmax: 2955, 2922, 2853, 1717,
1625, 1261 cm-1; 1H NMR (600 MHz, DMSO) δ (ppm): 15.11 (s, 1H, H-11), 8.65 (s, 1H, H-2),
8.37 (s, 1H, H-18), 7.94 – 7.90 (m, 1H, H-5), 7.66 – 7.46 (m, 4H, H-21, H-22), 7.29 (d, J =
8.1 Hz, 1H, H-8), 5.64 (s, 2H, H-19), 4.19 – 4.04 (m, 1H, H-9), 3.80 (s, 2H, H-16), 2.48 –
2.47 (m, 8H, H-13, H-14), 1.28 (q, J = 6.5 Hz, 2H, H-10b), 1.15 (q, J = 6.6 Hz, 2H, H-10a);
HRMS (ESI) m/z: [M+H]+ 581.1307 (calculated for C27H27BrFN6O3: 581.1321).
1-Cyclopropyl-6-fluoro-7-(4-((1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)-4-
oxo-1,4-dihydroquinoline-3-carboxylic acid (30).
Dark yellow solid, yield: 0.09 g (15%); m.p. 118 – 119 ,. IR vmax: 2957, 2924, 2858, 1725,
1
1625 cm-1; H NMR (600 MHz, CDCl3) δ (ppm): 14.95 (s, 1H, H-11), 8.72 (s, 1H, H-2), 8.23
(d, J = 8.7 Hz, 3H, H-18, H-22), 7.95 (d, J = 12.9 Hz, 1H, H-5), 7.44 (d, J = 8.7 Hz, 2H, H-
21), 7.34 (d, J = 7.0 Hz, 1H, H-8), 5.67 (s, 2H, H-19), 3.94 (s, 2H, H-16), 3.55 – 3.51 (m, 1H,
H-9), 3.45 (t, J = 19.7 Hz, 4H, H-14), 2.93 (t, J = 15.3, 4H, H-13), 1.34 (q, J = 6.9 Hz, 2H, H-
10b), 1.19 (q, J = 6.5 Hz, 2H, H-10a); 13C NMR (151 MHz, CDCl3) δ (ppm): 177.14 (C-4),
167.90 (C-11), 153.94 (C-6), 150.34 (C-23), 148.26 (C-2), 148.14 (C-17), 147.64 (C-20),
128.92 (C-21), 124.49 (C-22), 119.81 (C-18), 112.66 (C-5), 104.01 (C-8), 53.37 (C-19),
52.77 (C-13, C-14), 52.35 (C-16), 35.46 (C-9), 8.40 (C-10); HRMS (ESI) m/z: [M+H]+
548.2052 (calculated for C27H27FN7O5: 548.2058); Purity (HPLC): 81%.
1-Cyclopropyl-6-fluoro-4-oxo-7-(4-((1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-
yl)methyl)piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid (31).
Beige solid; yield: 0.11 g (49%); m.p. 122.3 – 123.7 ; IR vmax: 2956, 2923, 2853, 1725,
1
1625 cm-1; H NMR (600 MHz, CDCl3) δ (ppm): 15.00 (s, 1H, H-11), 8.71 (s, 1H, H-2), 7.94
(d, J = 13.0 Hz, 1H, H-5), 7.64 (d, J = 8.2 Hz, 2H, H-21), 7.57 (s, 1H, H-18), 7.40 (d, J = 8.1
Hz, 2H, H-22), 7.33 (d, J = 7.1 Hz, 1H, H-8), 5.61 (s, 2H, H-19), 3.82 (s, 2H, H-16), 3.54 –
3.51 (m, 1H, H-9), 1.36 (q, J = 6.5 Hz, 2H, H-10b), 1.18 (q, J = 6.5 Hz, 2H, H-10a); 13C NMR
(151 MHz, CDCl3) δ (ppm): 177.06 (C-4), 167.80 (C-11), 153.64 (C-6), 147.45 (C-2), 131.12
(C-24), 128.81 (C-21), 126.18 (C-22), 123.24 (C-18), 112.39 (C-5), 108.08 (C-3), 105.03 (C-
8), 53.67 (C-19), 53.08 (C-16), 52.50 (C-14), 49.45 (C-13), 35.33 (C-9), 8.26 (C-10); HRMS
(ESI) m/z: [M+H]+ 571.2019 (calculated for C28H26F4N6O3: 571.2081); Purity (HPLC): 85%.
1-Cyclopropyl-7-(4-((1-((3R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-
methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-
cyclopenta[a]phenanthren-3-yl)-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)-6-fluoro-4-oxo-
1,4-dihydroquinoline-3-carboxylic acid (32).
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