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Arch. Pharm. Chem. Life Sci. 2016, 349, 1–14
Fluorescent Chalcones and Their Cytotoxicity Mechanism
Archiv der Pharmazie
(3.67 mmol, 1.1 eq.) dissolved in EtOH (10 mL) was added
sodium hydroxide (10 mmol, 3.0 eq.). This mixture was stirred
under room temperature (or at 50°C for slow reactions) for
6–12 h. A yellow precipitate typically formed. Crude product
was collected via filtration followed by recrystallization in
cold MeOH to yield the pure product as a colored crystalline
solid. For products that did not precipitate, ethyl acetate/
H2O extraction followed by chromatography of the organic
residue was performed to purify the product with ethyl
acetate/hexanes as the eluents. Purities of all compounds
were >95% based on HPLC analysis. For known compounds,
1H NMR spectra were compared with literature reports and
found to be consistent. NMR and MS characterization of all
new compounds are reported below.
(E)-3-(4-(Dimethylamino)phenyl)-1-(4-ethoxy-2,5-
difluorophenyl)prop-2-en-1-one (C18)
Yield: 68%; 1H NMR (400 MHz, CDCl3): d 7.77 (1H, dd, J ¼ 15.6,
2.0 Hz), 7.64 (1H, dd, J ¼ 11.6, 6.8 Hz), 7.52 (2H, d, J ¼ 8.8 Hz),
7.24 (1H, dd, J ¼ 15.6, 2.4 Hz), 6.69 (1H, dd, J ¼ 12.0, 6.8 Hz),
6.67 (2H, d, J ¼ 8.8 Hz), 4.14 (2H, q, J ¼ 6.8 Hz), 3.03 (6H, s), 1.49
(3H, t, J ¼ 6.8 Hz); 13C NMR (125 MHz, CDCl3): d 186.03 (d,
J ¼ 4.3 Hz), 158.12 (dd, J ¼ 249.0, 1.5 Hz), 152.21, 151.17 (dd,
J ¼ 12.6, 11 Hz), 148.74 (dd, J ¼ 242.3, 2.2 Hz), 145.78, 130.69,
122.62, 119.97 (d, J ¼ 9.0 Hz), 119.27 (dd, J ¼ 15.2, 4.7 Hz),
117.25 (dd, J ¼ 21.2, 4.9 Hz), 111.89, 102.25 (dd, J ¼ 30.0,
1.3 Hz), 65.43, 40.19, 14.57; MS (ESI, positive) calculated m/z
for [MþH]þ: 332.1; found: 332.1.
(E)-3-(4-((2-Hydroxyethyl)(methyl)amino)phenyl)-1-(3,4,5-
(E)-1-(3,5-Dimethoxyphenyl)-3-(4-(dimethylamino)phenyl)-
trimethoxyphenyl)prop-2-en-1-one (C34)
prop-2-en-1-one (C8)
Yield: 59%; 1H NMR (500 MHz, CDCl3):
d 7.76 (1H, d,
Yield: 75%; 1H NMR (400 MHz, CDCl3):
d
7.79 (1H, d,
J ¼ 15.5 Hz), 7.52 (2H, d, J ¼ 9.0 Hz), 7.26 (1H, d, J ¼ 15.5 Hz),
7.25 (2H, s), 6.74 (2H, d, J ¼ 9.0 Hz), 3.93 (6H, s), 3.92 (3H, s),
3.84 (2H, t, J ¼ 5.5 Hz), 3.56 (2H, t, J ¼ 5.5 Hz), 3.05 (3H, s), 2.08
(1H, bs); 13C NMR (125 MHz, CDCl3): d 189.59, 153.14, 151.56,
145.77, 142.05, 134.45, 130.63, 123.05, 116.77, 112.12, 105.99,
61.07, 60.24, 56.47, 54.66, 39.06; MS (ESI, positive) calculated
m/z for [MþH]þ: 372.2; found: 372.2.
J ¼ 15.6 Hz), 7.54 (2H, d, J ¼ 8.8 Hz), 7.27 (1H, d, J ¼ 15.6 Hz),
7.14 (2H, d, J ¼ 2.2 Hz), 6.68 (2H, d, J ¼ 8.8 Hz), 6.64 (1H, t,
J ¼ 2.2 Hz), 3.86 (6H, s), 3.03 (6H, s); 13C NMR (100 MHz, CDCl3):
d 190.16, 160.73, 152.02, 145.92, 141.12, 130.39, 122.54,
116.82, 111.76, 106.11, 104.40, 55.55, 40.06; MS (ESI, positive)
calculated m/z for [MþH]þ: 312.2; found: 312.1.
(E)-3-(4-(Dimethylamino)phenyl)-1-(o-tolyl)prop-2-en-1-
one (C14)
(E)-3-(4-(Pyrrolidin-1-yl)phenyl)-1-(3,4,5-trimethoxyphenyl)-
prop-2-en-1-one (C35)
Yield: 70%; 1H NMR (400 MHz, CDCl3): d 7.44 (2H, d, J ¼ 9.0 Hz),
7.43 (1H, d, J ¼ 6.8 Hz), 7.37 (1H, d, J ¼ 16.0 Hz), 7.35 (1H, t,
J ¼ 7.2 Hz), 7.26 (1H, d, J ¼ 7.2 Hz), 7.25 (1H, t, J ¼ 6.8 Hz), 6.91
(1H, d, J ¼ 16.0 Hz), 6.67 (2H, d, J ¼ 9.0 Hz), 3.03 (6H, s), 2.42
(3H, s); 13C NMR (100 MHz, CDCl3): d 197.39, 152.22, 147.43,
140.22, 136.44, 131.12, 130.48, 129.86, 127.88, 125.45, 122.35,
122.17, 111.94, 40.23, 20.14; MS (ESI, positive) calculated m/z
for [MþH]þ: 266.2; found: 266.2.
Yield: 72%; 1H NMR (500 MHz, CDCl3):
d 7.80 (1H, d,
J ¼ 15.5 Hz), 7.54 (2H, d, J ¼ 8.5 Hz), 7.26 (1H, d, J ¼ 15.5 Hz),
7.26 (2H, s), 6.55 (2H, d, J ¼ 8.5 Hz), 3.94 (6H, s), 3.92 (3H, s),
3.39–3.30 (4H, m), 2.07–1.98 (4H, m). 13C NMR (125 MHz,
CDCl3): d 189.45, 153.12, 149.73, 146.23, 141.90, 134.70,
130.73, 122.13, 115.91, 111.86, 105.91, 61.05, 56.45, 47.70,
25.54; MS (ESI, positive) calculated m/z for [MþH]þ: 368.2;
found: 368.2.
(E)-3-(4-(Dimethylamino)phenyl)-1-(3,5-dimethylphenyl)-
(2E,4E)-5-(4-(Dimethylamino)phenyl)-1-(2-methoxyphenyl)-
prop-2-en-1-one (C16)
penta-2,4-dien-1-one (C38)
Yield: 75%; H NMR (400 MHz, CDCl3): d 7.55 (1H, dd, J ¼ 7.6,
1
Yield: 74%; 1H NMR (400 MHz, CDCl3):
d
7.78 (1H, d,
J ¼ 15.6 Hz), 7.61 (2H, s), 7.56 (2H, d, J ¼ 9.0 Hz), 7.32 (1H, d,
J ¼ 15.6 Hz), 7.19 (1H, s), 6.69 (2H, d, J ¼ 9.0 Hz), 3.04 (6H, s),
2.40 (6H, s); 13C NMR (100 MHz, CDCl3): d 190.99, 151.93,
145.41, 139.14, 137.99, 133.78, 130.31, 126.05, 122.71, 117.25,
111.77, 40.07, 21.26; MS (ESI, positive) calculated m/z for
[MþH]þ: 280.2; found: 280.1.
2.0 Hz), 7.46–7.34 (4H, m), 7.01 (1H, td, J ¼ 7.4, 1.0 Hz), 6.97
(1H, d, J ¼ 7.6 Hz), 6.88 (1H, d, J ¼ 15.2 Hz), 6.80 (1H, dd,
J ¼ 15.2, 11.2 Hz), 6.78 (1H, d, J ¼ 15.2 Hz), 6.67 (2H, d,
J ¼ 8.4 Hz), 3.89 (3H, s), 3.00 (6H, s); 13C NMR (125 MHz,
CDCl3): d 193.43, 157.85, 151.09, 145.64, 142.50, 132.26,
130.12, 129.90, 128.90, 128.02, 124.41, 122.74, 120.66, 112.12,
111.64, 55.80, 40.30; MS (ESI, positive) calculated m/z for
[MþH]þ: 308.2; found: 308.1.
(E)-3-(4-(Dimethylamino)phenyl)-1-(4-(trifluoromethyl)-
phenyl)prop-2-en-1-one (C17)
Yield: 81%; 1H NMR (400 MHz, CDCl3): d 8.07 (2H, d, J ¼ 8.2 Hz),
7.80 (2H, d, J ¼ 15.6 Hz), 7.74 (2H, d, J ¼ 8.2 Hz), 7.55 (2H, d,
J ¼ 8.8 Hz), 7.27 (1H, d, J ¼ 8.2 Hz), 6.69 (2H, d, J ¼ 8.8 Hz), 3.05
(6H, s), 2.40 (6H, s); 13C NMR (125 MHz, CDCl3): d 189.71,
152.42, 147.24, 142.19, 133.44 (q, J ¼ 32.3 Hz), 130.82, 128.66,
125.56 (q, J ¼ 3.8 Hz), 123.93 (q, J ¼ 271.0 Hz) 122.32, 116.33,
111.91, 40.18; MS (ESI, positive) calculated m/z for [MþH]þ:
319.1; found: 319.1.
(2E,4E)-5-(4-(Dimethylamino)phenyl)-1-(3-methoxyphenyl)-
penta-2,4-dien-1-one (C39)
Yield: 75%; 1H NMR (400 MHz, CDCl3): d 7.63 (1H, dd, J ¼ 14.8,
10.8 Hz), 7.55 (1H, d, J ¼ 7.6), 7.52 (1H, d, J ¼ 2.4 Hz), 7.40 (2H,
d, J ¼ 8.8 Hz), 7.10 (1H, dd, J ¼ 8.0, 1.2 Hz), 7.00–6.93 (2H, m),
6.85 (1H, dd, J ¼ 14.8, 10.8 Hz), 6.68 (2H, d, J ¼ 8.8 Hz), 3.87 (3H,
s), 3.01 (6H, s); 13C NMR (100 MHz, CDCl3): d 190.33, 159.91,
151.23, 146.54, 143.28, 140.27, 129.52, 129.04, 124.30, 122.78,
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