N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-3-fluorobenzenesulfonamide (**D2**)

Yield, 69%; white solid, m.p. 321–323 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 12.73 (s, 1H), 8.87 (d, *J* = 8.4 Hz, 1H), 8.04 (d, *J* = 8.5 Hz, 1H), 7.99 (d, *J* = 8.6 Hz, 1H), 7.88 (t, *J* = 7.9 Hz, 1H), 7.72 (d, *J* = 7.7 Hz, 1H), 7.63–7.56 (m, 2H), 7.53 (t, *J* = 7.6 Hz, 1H), 7.48 (s, 1H), 7.40 (t, *J* = 8.6, 2.7 Hz, 1H), 7.13 (d, *J* = 8.4 Hz, 1H), 4.15 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 163.31, 160.86, 154.96, 149.91 (d, *J* = 6.0 Hz), 147.97, 138.32, 132.65, 131.36 (d, *J* = 7.9 Hz), 129.95, 129.66, 124.02, 123.27, 122.12, 121.88 (d, *J* = 2.6 Hz), 121.56, 117.84 (d, *J* = 20.9 Hz), 116.39, 112.69, 112.46, 111.51, 107.10, 35.25. MS-ESI *m*/*z*: calcd for C22H15ClFN3O2S[M + H]+: 440.0558; found: 440.1708.

#### N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-4-fluorobenzenesulfonamide (**D3**)

Yield, 75%; white solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 12.71 (s, 1H), 8.96 (d, *J* = 8.4 Hz, 1H), 8.04 (d, *J* = 8.4 Hz, 1H), 7.99 (d, *J* = 8.7 Hz, 1H), 7.93 (m, 2H), 7.87 (d, *J* = 8.3 Hz, 1H), 7.53 (t, *J* = 7.7 Hz, 1H), 7.48 (s, 1H), 7.36 (t, *J* = 8.8 Hz, 2H), 7.15 (d, *J* = 8.4 Hz, 1H), 4.14 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 164.65, 162.19, 153.50, 149.74, 147.83, 144.10, 138.42, 137.97, 132.63, 129.84 (d, *J* = 7.4 Hz), 128.40 (d, *J* = 9.0 Hz, 2C), 124.02, 123.18, 121.96, 121.37, 116.38, 116.06 (2C), 115.84, 111.45, 35.20. MS-ESI *m*/*z*: calcd for C22H15ClFN3O2S[M + H]+: 440.0543; found: 440.1703.

N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-2-methylbenzenesulfonamide (**D4**)

Yield, 67%; yellow solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 12.64 (s, 1H), 9.05 (d, *J* = 8.4 Hz, 1H), 7.98 (m, 3H), 7.88 (t, *J* = 7.9 Hz, 1H), 7.54 (t, *J* = 7.6 Hz, 1H), 7.49 (s, 1H), 7.46 (d, *J* = 7.6 Hz, 1H), 7.36 (d, *J* = 13.3 Hz, 2H), 7.07 (d, *J* = 8.4 Hz, 1H), 4.14 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 154.98, 147.81, 145.37, 138.55, 136.23, 132.58, 132.25, 131.23, 130.11, 129.55, 126.33, 126.10, 124.72, 123.57, 123.00, 122.47, 121.73, 121.33, 116.34, 111.50, 106.04, 35.09, 20.48. MS-ESI *m*/*z*: calcd for C23H18ClN3O2S[M + H]+: 436.0808; found: 436.1984.

N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-4-methylbenzenesulfonamide (**D5**)

Yield, 84%; white solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 12.67 (s, 1H), 9.02 (d, J = 8.2 Hz, 1H), 8.10 (d, *J* = 8.3 Hz, 1H), 7.97 (d, *J* = 8.6 Hz, 1H), 7.87 (t, *J* = 7.8 Hz, 1H), 7.79 (d, *J* = 7.8 Hz, 2H), 7.52 (t, *J* = 7.8 Hz, 1H), 7.47 (s, 1H), 7.34 (d, *J* = 7.8 Hz, 2H), 7.13 (d, *J* = 8.3 Hz, 1H), 4.13 (s, 3H), 2.40 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 155.02, 147.63, 144.82, 140.83, 138.48, 137.78, 132.57, 130.07, 129.59, 129.42 (2C), 125.76 (2C), 124.13, 123.06, 122.36, 121.88, 121.32, 116.33, 112.41, 111.34, 99.99, 35.14, 21.41. MS-ESI *m*/*z*: calcd for C23H18ClN3O2S[M + H]+: 436.0804; found: 436.1940.
