# 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]
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.28 (brs, 1H), 8.11 (d, \(J\) = 7.6 Hz, 1H), 7.81-7.77 (m, 1H), 7.69-7.67 (m, 1H), 7.53 (d, \(J\) = 3.0 Hz, 1H), 7.48-7.44 (m, 1H), 6.36 (d, \(J\) = 3.0 Hz, 1H), and 2.41 (s, 3H) ppm; \({}^{13}\)C\({}^{[}\)H\(]\) NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.4, 156.0, 148.8, 144.4, 143.9, 134.4, 127.0, 126.0, 125.8, 120.9, 115.7, 108.8, and 13.4 ppm. 2-(5-Ethyl-furan-2-yl)quinazolin-4(3H)-one (**3v**). A yield of 0.265 g (85%), 9 h, pale yellow solid. Mp. = 187-188 \({}^{\circ}\)C (EtOH). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.30 (brs, 1H), 8.11 (d, \(J\) = 8.0 Hz, 1H), 7.80-7.77 (m, 1H), 7.69-7.67 (m, 1H), 7.52 (d, \(J\) = 3.0 Hz, 1H), 7.48-7.44 (m, 1H), 6.37 (d, \(J\) = 3.0 Hz, 1H), 2.75 (q, \(J\) = 7.6 Hz, 2H), and 1.25 (t, \(J\) = 7.6 Hz, 3H) ppm; \({}^{13}\)C\({}^{[}\)H\(]\) NMR (100 MHz,\(J\) = 2.0 Hz, 11H), 7.08 (s, 1H), 6.15 (br.s, 1H), and 4.07 (s, 3H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.8, 148.7, 146.7, 134.2, 129.9, 126.9, 125.6, 125.5, 123.9, 120.3, 114.7, 107.6, and 37.4 ppm. HRMS (ESI) Calcd for C\({}_{13}\)H\({}_{12}\)N\({}_{3}\)O [M + H]\({}^{+}\) 226.0975; Found 226.0979. 2-(Thiophen-2-yl)quinazolin-4(3H)-one (**3x**) [84]. A yield of 0.291 g (98%), 14.5 h, pale yellow solid. Mp. = 287 \({}^{\circ}\)C (EtOH) (lit. [84] 246-248 \({}^{\circ}\)C). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.58 (br.s, 1H), 8.23 (d, \(J\) = 2.8 Hz, 1H), 8.13-8.12 (m, 1H), 7.85-7.78 (m, 2H), 7.66-7.64 (m, 1H), 7.50-7.46 (m, 1H), and 7.24-7.22 (m, 1H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.7, 148.5, 147.8, 137.3, 134.5, 132.0, 129.3, 128.3, 126.8, 126.2, 125.9, and 120.8 ppm. 2-(Pyridin-4-yl)quinazolin-4(3H)-one (**3y**) [84]. A yield of 0.044 g (15%), 7.5 h, white solid. Mp. = 276-277 \({}^{\circ}\)C (EtOH) (lit. [84] 270-272 \({}^{\circ}\)C). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.69 (br.s, 1H), 8.78 (d, \(J\) = 4.4 Hz, 2H), 8.18 (br.d, \(J\) = 7.6 Hz, 1H), 8.11 (d, \(J\) = 4.4 Hz, 2H), 7.88-7.84 (m, 1H), 7.79-7.77 (m, 1H), and 7.59-7.55 (m, 1H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.9, 150.4, 150.1 (2C), 148.2, 139.8, 134.6, 127.6, 127.2, 125.8, 121.4 (2C), and 121.4 ppm. 2-(Naphthalene-2-yl)quinazolin-4(3H)-one (**3z**) [83]. A yield of 0.301 g (85%), 9 h, pale yellow solid. Mp. = 285-286 \({}^{\circ}\)C (EtOH) (lit. [83] 285-287 \({}^{\circ}\)C). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.59 (br.s, 1H), 8.82 (br.s, 1H), 8.32-8.30 (m, 1H), 8.19 (d, \(J\) = 7.6 Hz, 1H), 8.08-8.06 (m, 2H), 8.02-8.00 (m, 1H), 7.88-7.84 (m, 1H), 7.81-7.79 (m, 1H), 7.66-7.61 (m, 2H), and 7.56-7.52 (m, 1H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 162.2, 152.2, 148.6, 134.5, 134.1, 132.2, 129.9, 128.8, 128.03, 127.97, 127.8, 127.5, 127.4, 126.8, 126.5, 125.8, 121.4, and 121.0 ppm. 2-Cyclohexylquinazolin-4(3H)-one (**3 aa**) [87]. A yield of 0.261 g (88%), 8 h, white solid. Mp. = 222 \({}^{\circ}\)C (EtOAc) (lit. [87] 230-231 \({}^{\circ}\)C). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 11.99 (br.s, 1H), 8.07 (br.d, \(J\) = 7.6 Hz, 1H), 7.77-7.73 (m, 1H), 7.58 (br.d, \(J\) = 8.0 Hz, 1H), 7.45-7.42 (m, 1H), 2.61-2.55 (m, 1H), 1.92-1.89 (m, 2H), 1.80-1.77 (m, 2H), 1.69-1.55 (m, 3H), and 1.35-1.20 (m, 3H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.8, 160.6, 148.9, 134.0, 126.9, 125.7, 125.5, 120.9, 427.01 (2C), 25.4 (2C), and 25.2 ppm. 3-Amino-2-(1H-indol-3-yl)quinazolin-4(3H)-one (**3 ab**). A yield of 0.212 g (59%), 15 h, pale brown solid. Mp. = 235 \({}^{\circ}\)C, decomposition (EtOH).