Month 2018
Synthesis and Antimicrobial Activities of Novel Quinazolinone Acylhydrazone
Derivatives Containing the Indole Moiety
(E)-N0-((2-Chloro-1-(2-methoxybenzyl)-1H-indol-3-yl)
methylene)-4-oxo-3,4-dihydroquinazoline-2-carbohydrazide
(7i). Yellow solid; yield 79.67%; mp 210–211°С; 1H NMR
Ar-H), 7.87–7.83 (m, 1H, Ar-H), 7.73 (d, J = 7.7 Hz, 1H,
Ar-H), 7.67–7.62 (m, 1H, Ar-H), 7.61–7.56 (m, 1H,
Ar-H), 7.31–7.27 (m, 3H, Ar-H), 7.13–7.09 (m, 1H,
Ar-H), 5.62 (s, 2H, -CH2-) ppm; 13C NMR (100 MHz,
DMSO-d6) δ 161.39, 158.94, 158.40, 156.23, 146.39 (d,
J = 237.5 Hz), 146.21, 136.37, 135.31, 130.41, 130.33,
130.05, 128.94 (d, J = 3.8 Hz), 128.68, 128.16, 126.68
(d, J = 7.2 Hz), 125.33, 124.18, 123.92, 123.37, 122.57,
122.12, 116.11 (d, J = 20.6 Hz), 111.07, 108.66,
47.57 ppm; HRMS (m/z): 474.1126 ([M + H]+) Calcd for
(400 MHz, DMSO-d6) δ 12.40 (s, 1H, -CONH), 12.30
(s, 1H, quinazoline-NH), 8.95 (s, 1H, -N=CH), 8.38–8.34
(m, 1H, Ar-H), 8.20 (d, J = 7.8 Hz, 1H, Ar-H), 7.92 (t,
J = 7.0 Hz, 1H, Ar-H), 7.86 (d, J = 7.6 Hz, 1H, Ar-H),
7.64 (t, J = 7.1 Hz, 1H, Ar-H), 7.50–7.46 (m, 1H, Ar-H),
7.29–7.24 (m, 4H, Ar-H), 7.06 (d, J = 7.7 Hz, 1H, Ar-H),
6.81 (t, J = 7.5 Hz, 1H, Ar-H), 5.48 (s, 2H, -CH2-), 3.86
(s, 3H, -OCH3) ppm; 13C NMR (100 MHz, DMSO-d6) δ
161.40, 156.86, 156.20, 147.58, 146.23, 145.37, 136.46,
135.33, 130.41, 129.44, 128.69, 128.26, 127.08, 126.71,
124.51, 124.03, 123.90, 123.37, 122.43, 122.04, 120.98,
111.48, 111.19, 108.35, 55.98, 42.79 ppm; HRMS (m/z):
C25H18O2N5ClF: 474.1128.
(E)-N0-((2-Chloro-1-(3-fluorobenzyl)-1H-indol-3-yl)
methylene)-4-oxo-3,4-dihydroquinazoline-2-carbohydrazide
(7m). Yellow solid; yield 76.12%; mp 193–194°С; H
1
NMR (400 MHz, DMSO-d6) δ 12.35 (s, 1H, -CONH),
12.26 (s, 1H, quinazoline-NH), 8.97 (s, 1H, -N=CH),
8.39 (dd, J = 7.3, 1.4 Hz, 1H, Ar-H), 8.22 (d, J = 7.9 Hz,
1H, Ar-H), 8.18–8.14 (m, 1H, Ar-H), 7.94 (t, J = 7.6 Hz,
1H, Ar-H), 7.91–7.86 (m, 1H, Ar-H), 7.35–7.27 (m, 5H,
Ar-H), 7.11–7.05 (m, 2H, Ar-H), 5.62 (s, 2H, -CH2-)
ppm; 13C NMR (100 MHz, DMSO-d6) δ 161.77, 156.82,
147.13(d, J = 254.2 Hz), 145.22, 139.71, 138.95, 136.26,
135.30, 133.85, 129.83, 128.86 (d, J = 7.6 Hz), 128.14,
126.98, 126.73, 125.65, 124.78, 124.27, 122.65, 122.15,
120.69, 116.43 (d, J = 20.0 Hz), 111.65, 111.15, 108.68,
46.46 ppm; HRMS (m/z): 474.1131 ([M + H]+) Calcd for
486.1325 ([M + H]+) Calcd for C26H21O3N5Cl: 486.1327.
(E)-N0-((2-Chloro-1-(3-methoxybenzyl)-1H-indol-3-yl)
methylene)-4-oxo-3,4-dihydroquinazoline-2-carbohydrazide
1
(4j).
Yellow solid; yield 82.11%; mp 214–215°С; H
NMR (400 MHz, DMSO-d6) δ 12.45 (s, 1H, -CONH),
12.35 (s, 1H, quinazoline-NH), 8.97 (s, 1H, -N=CH),
8.38 (d, J = 6.8 Hz, 1H, Ar-H), 8.22 (t, J = 7.6 Hz, 1H,
Ar-H), 7.96–7.85 (m, 2H, Ar-H), 7.64 (dd, J = 15.4,
7.4 Hz, 2H, Ar-H), 7.30–7.22 (m, 3H, Ar-H), 6.85 (d,
J = 7.8 Hz, 1H, Ar-H), 6.77 (s, 1H, Ar-H), 6.67 (d,
J = 7.4 Hz, 1H, Ar-H), 5.55 (s, 2H, -CH2-), 3.71 (s, 3H, -
OCH3) ppm; 13C NMR (100 MHz, DMSO-d6) δ 161.18,
159.71, 155.99, 147.34, 146.02, 145.04, 138.46, 136.09,
135.08, 130.25, 129.73, 128.45, 128.01, 126.50, 123.89,
123.70, 123.15, 122.28, 121.85, 118.77, 113.03, 112.80,
111.03, 108.24, 55.27, 46.68 ppm; HRMS (m/z):
C25H18O2N5ClF: 474.1128.
(E)-N0-((2-Chloro-1-(4-fluorobenzyl)-1H-indol-3-yl)
methylene)-4-oxo-3,4-dihydroquinazoline-2-carbohydrazide
(7n). Yellow solid; yield 72.08%; mp 201–202°С; H
1
NMR (400 MHz, DMSO-d6) δ 12.41 (s, 1H, -CONH),
12.33 (s, 1H, quinazoline-NH), 8.97 (s, 1H, -N=CH),
8.40–8.35 (m, 1H, Ar-H), 8.23 (d, J = 6.8 Hz, 1H, Ar-H),
7.97–7.93 (m, 1H, Ar-H), 7.88 (m, J = 7.4 Hz, 1H,
Ar-H), 7.66 (t, J = 8.1 Hz, 2H, Ar-H), 7.35–7.29 (m, 2H,
Ar-H), 7.28–7.23 (m, 2H, Ar-H), 7.21–7.16 (m, 2H,
Ar-H), 5.58 (s, 2H, -CH2-) ppm; 13C NMR (100 MHz,
DMSO-d6) δ 161.39, 160.78, 156.21, 153.90, 147.58,
146.23, 145.23, 136.21, 135.32, 133.35 (d, J = 3.0 Hz),
129.79, 129.29 (d, J = 8.4 Hz), 128.25, 125.44 (d,
J = 257.4 Hz), 123.99, 123.38, 122.55, 122.12, 116.12
(d, J = 21.4 Hz), 111.21, 108.58, 46.33 ppm; HRMS
(m/z): 474.1140 ([M + H]+) Calcd for C25H18O2N5ClF:
486.1326 ([M + H]+) Calcd for C26H21O3N5Cl: 486.1327.
(E)-N0-((2-Chloro-1-(4-methoxybenzyl)-1H-indol-3-yl)
methylene)-4-oxo-3,4-dihydroquinazoline-2-carbohydrazide
1
(7k). Yellow solid; yield 81.23%; mp 201–202°С; H
NMR (400 MHz, DMSO-d6) δ 12.34 (s, 1H, -CONH),
12.27 (s, 1H, quinazoline-NH), 8.96 (s, 1H, -N=CH),
8.38 (dd, J = 16.5, 7.0 Hz, 1H, Ar-H), 8.22 (d,
J = 6.7 Hz, 1H, Ar-H), 8.17 (d, J = 6.7 Hz, 1H, Ar-H),
7.88 (t, J = 7.6 Hz, 2H, Ar-H), 7.74 (d, J = 7.9 Hz, 1H,
Ar-H), 7.68–7.62 (m, 2H, Ar-H), 7.34–7.25 (m, 2H, Ar-
H), 7.21–7.13 (m, 2H, Ar-H), 5.52 (d, J = 11.4 Hz, 2H,
-CH2-); 3.70 (s, 3H, -CH3) ppm; 13C NMR (100 MHz,
DMSO-d6) δ 160.76, 158.68, 157.52, 153.54, 145.57,
142.54, 135.72, 134.65, 130.60, 130.49, 128.36, 128.17,
127.83, 127.62, 126.05, 123.87, 123.50, 122.08, 121.70,
114.13, 112.80, 107.72, 55.02, 46.13 ppm; HRMS (m/z):
474.1128.
(E)-N0-((2-Chloro-1-(3-(trifluoromethyl)benzyl)-1H-indol-3-
yl)methylene)-4-oxo-3,4-dihydroquinazoline-2-carbohydrazide
1
(7o). Yellow solid; yield 67.18%; mp 196–197°С; H
486.1340 ([M + H]+) Calcd for C26H21O3N5Cl: 486.1327.
NMR (400 MHz, DMSO-d6) δ 12.42 (s, 1H, -CONH),
12.35 (s, 1H, quinazoline-NH), 8.97 (s, 1H, -N=CH),
8.40 (d, J = 6.2 Hz, 1H, Ar-H), 8.23 (d, J = 7.3 Hz, 1H,
Ar-H), 7.90 (dd, J = 22.2, 7.3 Hz, 2H, Ar-H), 7.75–7.52
(m, 5H, Ar-H), 7.33 (d, J = 5.9 Hz, 3H, Ar-H), 5.72 (s,
2H, -CH2-) ppm; 13C NMR (100 MHz, DMSO-d6) δ
161.39, 156.25, 147.57, 146.22, 145.18, 138.72, 136.29,
135.32, 130.92, 130.56, 130.04, 129.79, 128.70, 128.25,
(E)-N0-((2-Chloro-1-(2-fluorobenzyl)-1H-indol-3-yl)
methylene)-4-oxo-3,4-dihydroquinazoline-2-carbohydrazide
1
(7l).
Yellow solid; yield 78.05%; mp 191–192°С; H
NMR (400 MHz, DMSO-d6) δ 12.39 (s, 1H, -CONH),
12.32 (s, 1H, quinazoline-NH), 8.94 (s, 1H, -N=CH),
8.39–8.34 (m, 1H, Ar-H), 8.20 (dd, J = 7.9, 1.1 Hz, 1H,
Ar-H), 8.15 (d, J = 9.1, 1H, Ar-H), 7.94–7.88 (m, 1H,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet