7-Hydroxy-8-[(dimethylamino)methyl]-5-methoxy-3-(4-fluorophenyl)-4H-chromen-4-one (6c). C H FNO ,
19 18
4
yield 73%, mp 210–211°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm, J/Hz): 2.43 [6H, s, (CH ) N], 3.84 (2H, s, 8-CH ), 3.93
3
3 2
2
3
3
3
4
(3H, s, 5-OCH ), 6.34 (1H, s, H-6), 7.08 (2H, dd, J = 8.8, J = 8.8, H-3ꢀ, H-5ꢀ), 7.36 (2H, dd, J = 8.8, J = 5.5,
3
HH
HF
HH
HF
H-2ꢀ, H-6ꢀ), 7.74 (1H, s, H-2), 10.12 (1H, s, 7-OH).
7-Hydroxy-8-[(dimethylamino)methyl]-5-methoxy-3-(4-chlorophenyl)-4H-chromen-4-one Hydrochloride (6d).
3
C H ClNO 4HCl, yield 36%, mp 197–198°C. PMR spectrum (400 MHz, DMSO-d , ꢁ, ppm, J/Hz): 2.77 [6H, d, J = 4.4,
19 18
4
6
3
(CH ) N], 3.82 (3H, s, 5-OCH ), 4.30 (2H, d, J = 4.4, 8-CH ), 6.72 (1H, s, H-8), 7.46–7.55 (4H, m, H-2ꢀ, H-3ꢀ, H-5ꢀ, H-6ꢀ),
3 2
3
2
+
8.26 (1H, s, H-2), 9.97 (1H, m, NH ), 11.91 (1H, s, 7-OH).
7-Hydroxy-5-methoxy-8-(piperidin-1-ylmethyl)-3-phenyl-4H-chromen-4-one (7a). C H NO , yield 51%,
22 23
4
mp 184–185°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm): 1.17–3.55 (10H, m, piperidine protons), 3.79 (3H, s, 5-OCH ),
3
3
4.11 (2H, s, 8-CH ), 6.51 (1H, s, H-6), 7.28–7.38 (3H, m, H-2ꢀ, H-4ꢀ, H-6ꢀ), 7.43-7.47 (2H, m, H-3ꢀ, H-5ꢀ), 7.73 (1H, s, H-2).
2
7-Hydroxy-5-methoxy-3-(4-methoxyphenyl)-8-(piperidin-1-ylmethyl)-4H-chromen-4-one (7b). C H NO ,
23 25
5
yield 51%, mp 189–190°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm, J/Hz): 1.17–3.33 (10H, m, piperidine protons), 3.83
3
3
(3H, s, 4ꢀ-OCH ), 3.89 (2H, s, 8-CH ), 3.92 (3H, s, 5-OCH ), 6.31 (1H, s, H-6), 6.93 (2H, d, J = 8.5, H-3ꢀ, H-5ꢀ), 7.47 (2H, d,
3
2
3
3
J = 8.5, H-2ꢀ, H-6ꢀ), 7.72 (1H, s, H-2), 9.05 (1H, s, 7-OH).
7-Hydroxy-5-methoxy-8-(piperidin-1-ylmethyl)-3-(4-fluorophenyl)-4H-chromen-4-one (7c). C H FNO , yield
22 22
4
53%, mp 197–198°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm, J/Hz): 1.44–3.25 (10H, m, piperidine protons), 3.89 (3H, s,
3
3
3
3
5-OCH ), 3.98 (2H, s, 8-CH ), 6.40 (1H, s, H-6), 7.08 (2H, dd, J = 8.8, J = 8.8, H-3ꢀ, H-5ꢀ), 7.50 (2H, dd, J = 8.8,
3
2
HH
HF
HH
4
J
= 5.5, H-2ꢀ, H-6ꢀ), 7.73 (1H, s, H-2).
HF
7-Hydroxy-5-methoxy-8-(piperidin-1-ylmethyl)-3-(4-chlorophenyl)-4H-chromen-4-one (7d). C H ClNO ,
22 22
4
yield 62%, mp 212–213°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm, J/Hz): 1.19–3.35 (10H, m, piperidine protons), 3.90
3
3
3
(2H, s, 8-CH ), 3.92 (3H, s, 5-OCH ), 6.31 (1H, s, H-6), 7.36 (2H, d, J = 8.4, H-3ꢀ, H-5ꢀ), 7.48 (2H, d, J = 8.4, H-2ꢀ, H-6ꢀ),
2
3
7.74 (1H, s, H-2), 10.55 (1H, s, 7-OH).
7-Hydroxy-5-methoxy-3-(2-methoxyphenyl)-8-(piperidin-1-ylmethyl)-4H-chromen-4-one (7e). C H NO , yield
23 25
5
78%, mp 167–168°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm): 1.22–3.23 (10H, m, piperidine protons), 3.79 (3H, s,
3
2ꢀ-OCH ), 3.90 (3H, s, 5-OCH ), 3.91 (2H, s, 8-CH ), 6.30 (1H, s, H-6), 6.91–7.02 (2H, m, H-3ꢀ, H-5ꢀ), 7.26–7.38 (2H, m,
3
3
2
H-4ꢀ, H-6ꢀ), 7.71 (1H, s, H-2).
7-Hydroxy-8-[(4-methylpiperazin-1-yl)methyl]-5-methoxy-3-phenyl-4H-chromen-4-one (8a). C H N O , yield
22 24
2 4
60%, mp 189–190°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm): 2.14–3.10 (11H, m, piperazine protons), 3.93 (3H, s, 5-
3
OCH ), 3.95 (2H, s, 8-CH ), 6.33 (1H, s, H-6), 7.32–7.43 (3H, m, H-2ꢀ, H-4ꢀ, H-6ꢀ), 7.50–7.56 (2H, m, H-3ꢀ, H-5ꢀ), 7.71 (1H,
3
2
s, H-2).
7-Hydroxy-8-[(4-methylpiperazin-1-yl)methyl]-5-methoxy-3-(4-chlorophenyl)-4H-chromen-4-one (8d).
C H ClN O , yield 55%, mp 195–197°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm, J/Hz): 2.04–3.22 (11H, m, piperazine
22 23
2
4
3
3
3
protons), 3.93 (3H, s, 5-OCH ), 3.95 (2H, s, 8-CH ), 6.33 (1H, s, H-6), 7.36 (2H, d, J = 8.5, H-3ꢀ, H-5ꢀ), 7.48 (2H, d, J = 8.5,
3
2
H-2ꢀ, H-6ꢀ), 7.76 (1H, s, H-2).
7-Hydroxy-8-[(4-methylpiperazin-1-yl)methyl]-5-methoxy-3-(2-methoxyphenyl)-4H-chromen-4-one (8e).
C H N O , yield 83%, mp 164–166°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm): 2.13–3.15 (11H, m, piperazine protons),
23 26
2
5
3
3.78 (3H, s, 2ꢀ-OCH ), 3.90 (3H, s, 5-OCH ), 3.95 (2H, s, 8-CH ), 6.31 (1H, s, H-6), 6.92–7.03 (2H, m, H-3ꢀ, H-5ꢀ), 7.26–7.38
3
3
2
(2H, m, H-4ꢀ, H-6ꢀ), 7.74 (1H, s, H-2).
7-Hydroxy-5-methoxy-3-(4-methoxyphenyl)-8-(morpholin-4-ylmethyl)-4H-chromen-4-one (9b). C H NO ,
22 23
6
yield 73%, mp 199–200°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm, J/Hz): 2.30–3.03 (4H, m, 3ꢀꢀ-NCH , 5ꢀꢀ-NCH ), 3.74–
3
2
2
3
3.87 [7H, m + s, O(CH ) , 4ꢀ-OCH ], 3.89 (3H, s, 5-OCH ), 3.98 (2H, s, 8-CH ), 6.36 (1H, s, H-6), 6.92 (2H, d, J = 8.8,
H-3ꢀ, H-5ꢀ), 7.46 (2H, d, J = 8.8, H-2ꢀ, H-6ꢀ), 7.74 (1H, s, H-2).
2 2
3
3
3
2
7-Hydroxy-5-methoxy-8-(morpholin-4-ylmethyl)-3-(4-fluorophenyl)-4H-chromen-4-one (9c). C H FNO ,
21 20
5
yield 88%, mp 237–239°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm, J/Hz): 2.38–3.08 (4H, m, 3ꢀꢀ-NCH , 5ꢀꢀ-NCH ), 3.71–
3
2
2
3
3
3.89 [4H, m, O(CH ) ], 3.92 (3H, s, 5-OCH ), 3.98 (2H, s, 8-CH ), 6.38 (1H, s, H-6), 7.09 (2H, dd, J = 8.8, J = 8.8,
H-3ꢀ, H-5ꢀ), 7.50 (2H, dd, J = 8.8, J = 5.4, H-2ꢀ, H-6ꢀ), 7.76 (1H, s, H-2).
2 2
3
2
HH
HF
3
4
HH
HF
7-Hydroxy-5-methoxy-8-(morpholin-4-ylmethyl)-3-(4-chlorophenyl)-4H-chromen-4-one (9d). C H ClNO ,
21 20
5
yield 83%, mp 210–211°C. PMR spectrum (400 MHz, CDCl , ꢁ, ppm, J/Hz): 2.38–3.23 (4H, m, 3ꢀꢀ-NCH , 5ꢀꢀ-NCH ), 3.72–
3
2
2
3
3.86 [4H, m, O(CH ) ], 3.89 (3H, s, 5-OCH ), 4.00 (2H, s, 8-CH ), 6.38 (1H, s, H-6), 7.35 (2H, d, J = 8.5, H-3ꢀ, H-5ꢀ), 7.46
2 2
3
2
3
(2H, d, J = 8.5, H-2ꢀ, H-6ꢀ), 7.76 (1H, s, H-2).
240