8-chloro-11-(2-(2-fluorophenyl)hydrazineyl)-5-methyl-5H-indolo[2,3-b]quinoline (**B2**)

Yield, 56%; white solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, Methanol-*d*4) *δ* 8.87–8.71 (m, 1H), 8.51 (d, *J* = 8.9 Hz, 1H), 8.20 (d, *J* = 8.8 Hz, 1H), 8.07 (t, *J* = 8.0 Hz, 1H), 7.72 (t, *J* = 7.8 Hz, 1H), 7.59 (s, 1H), 7.29–7.18 (m, 2H), 7.00 (t, *J* = 7.7 Hz, 1H), 6.93–6.82 (m, 2H), 4.24 (s, 3H). 13C NMR (100 MHz, Methanol-*d*4) *δ* 153.54, 149.86, 139.43, 137.74, 136.47, 134.43, 131.86, 126.02, 125.55, 123.16, 121.01, 117.82, 116.68, 116.50, 116.18, 114.74, 112.40, 98.61, 57.28, 36.21. MS-ESI *m*/*z*: calcd for C22H16ClFN4[M + H]+: 391.1048; found: 391.2159.

#### 8-chloro-11-(2-(3-fluorophenyl)hydrazineyl)-5-methyl-5H-indolo[2,3-b]quinoline (**B3**)

Yield, 73%; gray solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 8.77 (s, 1H), 8.47 (d, *J* = 8.8 Hz, 1H), 8.19 (d, *J* = 8.8 Hz, 1H), 8.06 (d, *J* = 8.5 Hz, 1H), 7.71 (t, *J* = 7.8 Hz, 1H), 7.57 (s, 1H), 7.32–7.19 (m, 2H), 6.76 (d, *J* = 8.1 Hz, 1H), 6.66 (m, 2H), 4.22 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 152.56, 138.53, 136.91, 133.54, 131.32, 131.23, 131.09, 124.68, 122.46, 120.00, 116.89, 113.85, 111.50, 109.38, 107.29, 107.07, 100.53, 100.27, 97.70, 35.27. MS-ESI *m*/*z*: calcd for C22H16ClFN4[M + H]+: 391.1045; found: 391.2103.

#### 8-chloro-11-(2-(4-fluorophenyl)hydrazineyl)-5-methyl-5H-indolo[2,3-b]quinoline (**B4**)

Yield, 71%; yellow solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 8.73 (s, 1H), 8.55 (d, *J* = 8.8 Hz, 1H), 8.19 (d, *J* = 8.8 Hz, 1H), 8.06 (t, *J* = 7.9 Hz, 1H), 7.70 (t, *J* = 7.8 Hz, 1H), 7.58 (s, 1H), 7.27–7.20 (m, 1H), 7.05 (t, *J* = 8.7 Hz, 2H), 6.94 (d, *J* = 9.0 Hz, 2H), 4.25 (s, 3H). 13C NMR (100 MHz, DMSO) *δ* 153.54, 144.97, 138.62, 135.38, 134.13, 131.84, 129.43, 127.46, 125.78, 125.61, 122.51, 121.45, 117.37(2C), 116.74(2C), 116.51, 115.73, 115.64, 114.31, 111.99, 33.53. MS-ESI *m*/*z*: calcd for C22H16ClFN4[M + H]+: 391.1061; found: 391.2028.

#### 8-chloro-11-(2-(2,4-difluorophenyl)hydrazineyl)-5-methyl-5H-indolo[2,3-b]quinoline (**B5**)

Yield, 56%; white solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, Methanol-*d*4) *δ* 8.76 (s, 1H), 8.50 (d, *J* = 8.8 Hz, 1H), 8.20 (d, *J* = 8.7 Hz, 1H), 8.12–8.01 (m, 1H), 7.72 (t, *J* = 7.7 Hz, 1H), 7.60 (s, 1H), 7.24 (m, 2H), 6.90 (m, 2H), 4.25 (s, 3H). 13C NMR (100 MHz, CD3OD\_SPE) *δ* 153.30, 152.37, 150.85, 149.28, 141.92, 139.78, 138.11, 134.37, 131.96, 128.69, 127.04, 125.50, 123.72, 120.55, 118.96, 116.90, 115.40, 114.75, 113.19, 107.73, 104.57, 36.00. MS-ESI *m*/*z*: calcd for C22H15ClF2N4[M + H]+: 409.0953; found: 409.2040.

8-chloro-5-methyl-11-(2-(o-tolyl)hydrazineyl)-5H-indolo[2,3-b]quinoline (**B6**)

Yield, 74%; white solid, m.p. 255–256 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 8.82 (s, 1H), 8.46 (d, *J* = 9.3 Hz, 1H), 8.20 (d, *J* = 8.7 Hz, 1H), 8.07 (t, *J* = 8.0 Hz, 1H), 7.72 (t, *J* = 7.7 Hz, 1H), 7.59 (s, 1H), 7.22 (d, *J* = 16.6 Hz, 2H), 7.04 (t, *J* = 7.7 Hz, 1H), 6.83 (t, *J* = 7.4 Hz, 1H), 6.74 (d, *J* = 7.9 Hz, 1H), 4.24 (s, 3H), 3.51 (s, 3H). 13C NMR (100 MHz, DMSO) *δ* 153.17, 148.78, 145.56, 138.03, 133.49, 133.00, 131.11, 130.93, 129.97, 127.17, 124.35, 123.54, 122.84, 122.11, 120.95, 119.56, 117.02, 114.44, 113.76, 112.53, 111.60, 33.86, 20.16. MS-ESI *m*/*z*: calcd for C23H19ClN4[M + H]+: 387.1298; found: 387.2787.
