# The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives
## 3 Materials and Methods
#### Synthesis of 2-(1\(H\)-indol-3-yl)quinazolin-4(3\(h\))-one (**3a**) [80]
The products **3b,c,e,s,u,v,y,z,aa** were recrystallized from a suitable solvent without prior purification using column chromatography. 2-(1H-Indol-3-yl)quinazolin-4(3H)-one (**3a**) [80]. A yield of 0.326 g (96%), 14 h, white solid. Mp. \(\geq\) 320 \({}^{\circ}\)C, decomposition (EtOH, lit. [80] > 300 \({}^{\circ}\)C). All the spectral data of 2-(1\(H\)-indol-3-yl)quinazolin-4(3\(H\))-one (**3a**) were consistent with those described above. 2-(1-Methyl-1H-indol-3-yl)quinazolin-4(3H)-one (**3b**) [83]. A yield of 0.211 g (59%), 43 h, white solid. Mp. \(\geq\) 324 \({}^{\circ}\)C, decomposition (EtOH, lit. [83] 290-295 \({}^{\circ}\)C). 1\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.07 (s, 1H), 8.72-8.70 (m, 1H), 8.51 (s, 1H), 8.12-8.10 (m, 1H), 7.80-7.71 (m, 2H), 7.55 (br, \(J\) = 7.6 Hz, 1H), 7.43-7.39 (m, 1H), 7.33-7.25 (m, 2H), and 3.88 (s, 3H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 162.0, 149.9, 149.6, 137.3, 134.2, 132.8, 126.8, 125.9, 125.7, 125.0, 122.6, 122.4, 121.1, 120.4, 110.3, 107.6, and 332. ppm. 2-(1-Ethyl-1H-indol-3-yl)quinazolin-4(3H)-one (**3c**). A yield of 0.327 g (87%), 47 h, pale beige solid. Mp. = 283-284 \({}^{\circ}\)C (EtOH). 1\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.05 (br.s, 1H), 8.72 (d, \(J\) = 7.5 Hz, 1H), 8.62 (br.s, 1H), 8.12 (d, \(J\) = 7.6 Hz, 1H), 7.80-7.72 (m, 2H), 7.58 (d, \(J\) = 7.6 Hz, 1H), 7.43-7.39 (m, 1H), 7.31-7.24 (m, 2H), 4.27 (q, \(J\) = 7.2 Hz, 2H), and 1.48 (t, \(J\) = 7.2 Hz, 3H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.9, 149.9, 149.7, 136.5, 134.2, 131.1, 126.9, 126.0, 125.7, 125.0, 122.51, 122.50, 121.1, 120.4, 110.3, 107.7, 40.8, and 14.7 ppm. HRMS (ESI) Calcd for C\({}_{18}\)H\({}_{16}\)N\({}_{3}\)O [M + H]\({}^{+}\) 290.1288; Found 290.1278. 2-(1-Isopropyl-1H-indol-3-yl)quinazolin-4(3H)-one (**3d**). A yield of 0.319 g (81%), 24 h, beige solid. Mp. = 275-276 \({}^{\circ}\)C (EtOH). 1\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.03 (br.s, 1H), 8.78 (br.s, 1H), 8.73-8.71 (m, 1H), 8.10 (br.d, \(J\) = 7.6 Hz, 1H), 7.80-7.72 (m, 2H), 7.62 (br.d, \(J\) = 7.6 Hz, 1H), 7.43-7.39 (m, 1H), 7.31-7.24 (m, 2H), 4.89-4.80 (m, 1H), 1.54 (s, 3H), and 1.52 (s, 3H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.9, 150.0, 149.7, 136.3, 134.2, 128.5, 126.9, 126.0, 125.7, 125.0, 122.5, 122.4, 121.1, 120.3, 110.4, 107.8, 47.1, and 22.3 (2C) ppm. HRMS (ESI) Calcd for C\({}_{19}\)H\({}_{18}\)N\({}_{3}\)O [M + H]\({}^{+}\) 304.1444; Found 304.1452. 2-(1-Butyl-1H-indol-3-yl)quinazolin-4(3H)-one (**3e**). A yield of 0.317 g (77%), 55 h, white solid. Mp. = 264-265 \({}^{\circ}\)C (EtOH). 1\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.05 (br.s, 1H), 8.72 (br.d, \(J\) = 8.0 Hz, 1H), 8.59 (s, 1H), 8.12-8.10 (m, 1H), 7.80-7.71 (m, 2H), 7.60 (d, \(J\) = 8.0 Hz, 1H), 7.43-7.39 (m, 1H), 7.31-7.24 (m, 2H), 4.25 (t, \(J\) = 7.2 Hz, 2H), 1.88-1.81 (m, 2H), 1.36-1.31 (m, 2H), and 0.94 (t, \(J\) = 7.2 Hz, 3H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz,DMSO-\(d_{6}\)) \(\delta\) = 161.9, 149.9, 149.6, 136.8, 134.2, 131.8, 126.8, 125.9, 125.6, 125.0, 122.51, 122.48, 121.0, 120.3, 110.4, 107.6, 45.6, 31.2, 19.3, and 13.4 ppm. HRMS (ESI) Calcd for C\({}_{20}\)H\({}_{20}\)N\({}_{3}\)O [M + H]\({}^{+}\) 318.1601; Found 318.1598. 2-(1-Benzyl-1H-indol-3-yl)quinazolin-4(3H)-one (**3f**). A yield of 0.411 g (90%), 19 h, white solid. Mp. = 307-308 \({}^{\circ}\)C (EtOH). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.12 (brs., 1H), 8.73-8.71 (m, 1H), 8.66 (brs., 1H), 8.11 (d, \(J\) = 7.6 Hz, 1H), 7.80-7.72 (m, 2H), 7.63-7.60 (m, 1H), 7.43-7.40 (m, 1H), 7.36-7.33 (m, 4H), 7.31-7.24 (m, 3H), and 5.50 (s, 2H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.9, 149.8, 149.6, 137.0, 136.7, 134.2, 132.2, 128.6 (2C), 127.6, 127.4 (2C), 126.9, 126.1, 125.7, 125.1, 122.7, 122.5, 121.2, 120.4, 110.7, 108.3, and 49.7 ppm. HRMS (ESI) Calcd for C\({}_{23}\)H\({}_{18}\)N\({}_{3}\)O [M + H]\({}^{+}\) 352.1444; Found 352.1451.