JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
865
overnight. The obtained precipitate was filtered, washed with cold 8. (E)-3-(benzo[d][1,3]dioxol-4-yl)-1–(3-chlorophenyl)prop-2-en-1-one
ꢁ
1
water and recrystallized from ethanol to produce chalcones 1–22.
Yellow crystals, yield ¼ 72%, m.p. ¼ 79–83 C. H NMR (700 MHz,
Chloroform-d) d 8.08–7.98 (m, 1H), 7.96–7.87 (m, 1H), 7.85–7.65
(
1
m, 2H), 7.63–7.53 (m, 1H), 7.52–7.40 (m, 1H), 7.04 (q, J ¼ 4.9 Hz,
1
3
1
.
(E)-3–(4-(dimethylamino)phenyl)-1–(3-(trifluoromethyl)phenyl)-
H), 6.91 (s, 2H), 6.16 (s, 2H). C NMR (176 MHz, CDCl ) d 189.3,
3
prop-2-en-1-one
148.1, 146.9, 140.2, 139.8, 134.9, 132.7, 130.0, 128.6, 126.6, 124.0,
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1
Orange crystals, yield ¼ 50%, m.p. ¼ 96–99 C. H NMR (600 MHz, 123.6, 122.0, 117.8, 110.3, 101.6. EI-MS (m/z): calculated 286.0,
þ
Chloroform-d) d 8.25 (s, 1H), 8.18 (d, J ¼ 8.4 Hz, 1H), 7.84 (d, observed 286.0 (M ).
J ¼ 15 Hz, 1H), 7.8 (d, J ¼ 8.4 Hz, 1H), 7.63 (dd, J ¼ 7.8 Hz, 7.8, 1H),
7
3
.57 (d, J ¼ 9 Hz, 2H), 7.31 (d, J ¼ 16 Hz, 1H), 6.71 (d, J ¼ 9 Hz, 2H),
.10 (s, 6H).
9. (E)-3–(4-bromophenyl)-1–(4-(methylsulfonyl)phenyl)prop-2-en-1-one
þ
ꢁ
1
EI-MS (m/z): calculated 319.1, observed 319.1 (M ).
White crystals, yield ¼ 71%, m.p. ¼ 206–210 C. H NMR (700 MHz,
Chloroform-d) d 8.18 (d, J ¼ 7.7 Hz, 2H), 8.12 (d, J ¼ 8.0 Hz, 2H),
7
.80 (d, J ¼ 15.9 Hz, 1H), 7.60 (d, J ¼ 7.7 Hz, 2H), 7.55 (d, J ¼ 8.1 Hz,
13
2
. (E)-3–(4-(dimethylamino)phenyl)-1–(4-(trifluoromethyl)phenyl)
2H), 7.49 (d, J ¼ 15.9 Hz, 1H), 3.13 (s, 3H).
C NMR (176 MHz,
prop-2-en-1-one
CDCl ) d 189.2, 145.3, 143.9, 142.3, 133.2, 132.4, 130.0, 129.3,
3
ꢁ
Yellow crystals, yield ¼ 62%, m.p. ¼ 141–145 C. The obtained 127.9, 125.6, 121.8, 44.4. EI-MS (m/z): calculated 364.9, observed
1
6
þ
analytical data matched with the previously published finding .
364.9 (M ).
3
. (E)-1–(4-bromophenyl)-3–(4-(dimethylamino)phenyl)prop-2-en-1-one 10. (E)-3–(4-bromo-2-methoxyphenyl)-1–(4-(methylsulfonyl)phenyl)-
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1
Yellow crystals, yield ¼ 54%, m.p. ¼ 139–142 C. H NMR prop-2-en-1-one
ꢁ
1
(
600 MHz, Chloroform-d) d 7.87 (dd, J ¼ 6.6, 1.8 Hz, 2H), 7.80 (d, Yellow crystals, yield ¼ 67%, m.p. ¼ 199–203 C. H NMR
J ¼ 15.6 Hz, 1H), 7.62 (dd, J ¼ 6.0, 1.2 Hz, 2H), 7.55 (d, J ¼ 9 Hz, 2H), (700 MHz, Chloroform-d)
d
8.17 (d, J ¼ 8.6 Hz, 2H), 8.11 (d,
1
3
7
.27 (d, J ¼ 15.0 Hz, 1H), 6.70 (d, J ¼ 9 Hz, 2H), 3.10 (s, 6H).
C
J ¼ 7.2 Hz, 2H), 8.05 (d, J ¼ 16.3 Hz, 1H), 7.57 (d, J ¼ 15.6 Hz, 1H),
NMR (151 MHz, CDCl
3
) d 189.4, 152.2, 146.4, 137.8, 131.7, 130.6, 7.51 (d, J ¼ 8.3 Hz, 1H), 7.19 (d, J ¼ 8.1 Hz, 1H), 7.15–7.08 (m, 1H),
1
3
1
30.0, 127.1, 122.4, 116.2, 111.8, 40.1 EI-MS (m/z): calculated 329.0, 3.96 (s, 3H), 3.13 (s, 3H). C NMR (176 MHz, CDCl ) d 189.9, 159.3,
3
þ
observed 329.0 (M ).
143.6, 142.7, 141.1, 130.4, 129.3, 127.8, 126.3, 124.2, 122.5, 122.4,
1
3
15.1, 56.0, 44.4. EI-MS (m/z): calculated 395.9, observed
95.9 (M ).
þ
4
. (E)-1–(4-chlorophenyl)-3–(4-(dimethylamino)phenyl)prop-2-en-1-one
Yellow crystals, yield ¼ 53%,
The obtained analytical data matched with the previously 11. (E)-3–(3-bromophenyl)-1–(4-(methylthio)phenyl)prop-2-en-1-one
1
7
1
ꢁ
published .
Yellow crystals, yield ¼ 67%, m.p. ¼ 139–143 C. H NMR
(700 MHz, Chloroform-d) d 8.06–7.94 (m, 2H), 7.82 (s, 1H), 7.75 (d,
J ¼ 15.3 Hz, 1H), 7.64–7.47 (m, 3H), 7.41–7.23 (m, 3H), 2.57 (s, 3H).
5
. (E)-3-(benzo[d][1,3]dioxol-4-yl)-1–(4-bromophenyl)prop-2-en-1-one
13
C NMR (176 MHz, CDCl ) d 188.7, 146.1, 142.6, 137.1, 134.1,
3
ꢁ
1
Yellow crystals, yield ¼ 55%, m.p. ¼ 96–100 C. H NMR (500 MHz,
Chloroform-d) d 7.92 (d, J ¼ 8.3 Hz, 2H), 7.77 (d, J ¼ 7.7 Hz, 2H),
1
33.2, 130.8, 130.5, 129.0, 127.3, 125.1, 123.1, 122.9, 14.8. EI-MS
þ
(m/z): calculated 333.9, observed 333.9 (M ).
7
6
1
1
.67 (d, J ¼ 8.5 Hz, 2H), 7.10–6.99 (m, 1H), 6.90 (d, J ¼ 3.6 Hz, 2H),
13
.15 (s, 2H).
C NMR (176 MHz, CDCl3) d 189.6, 148.1, 146.8,
39.9, 136.9, 131.9, 130.1, 127.9, 124.0, 123.6, 122.0, 117.9, 110.2, 12. (E)-1–(4-fluorophenyl)-3–(4-nitrophenyl)prop-2-en-1-one
þ
1
ꢁ
01.6 EI-MS (m/z): calculated 331.9, observed 331.9 (M ).
Yellow crystals, yield ¼ 70%, m.p. ¼ 165–169 C. H NMR 400 MHz;
CDCl ) d (ppm): 8.27 (d, J ¼ 8.7, 2H), 8.10 (dd, J ¼ 8.7, 5.4 Hz, 2H),
3
7
.81 (d, J ¼ 15.8 Hz, 1H), 7.77 (d, J ¼ 8.8 Hz, 2H),) , 7.60 (d,
13
6
1
. (E)-3-(benzo[d][1,3]dioxol-4-yl)-1–(4-chlorophenyl)prop-2-en-
J ¼ 15.7 Hz, 1H), 7.19 (d, J ¼ 8.5 Hz 2H., C NMR (176 MHz, CDCl
3
)
-one
d 188.0, 166.7, 165.2, 148.6, 141.8, 140.9, 133.9, 133.9, 131.3, 131.3,
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1
Yellow crystals, yield ¼ 50%, m.p. ¼ 83–87 C. H NMR (500 MHz,
Chloroform-d) d 8.00 (d, J ¼ 8.5 Hz, 2H), 7.75 (d, J ¼ 4.3 Hz, 2H),
1
29.0, 128.6, 125.2, 124.3, 123.9, 116.1, 116.0. EI-MS (m/z): calcu-
þ
lated 271.0, observed 271.0 (M ).
7
.50 (d, J ¼ 8.5 Hz, 2H), 7.04 (dq, J ¼ 7.9, 4.0 Hz, 1H), 6.89 (d,
13
J ¼ 3.6 Hz, 2H), 6.15 (s, 2H). C NMR (176 MHz, CDCl ) d 189.3,
3
1
1
2
48.0, 146.8, 139.8, 139.2, 136.5, 130.0, 128.4, 124.0, 123.6, 122.0, 13. (E)-1–(4-chlorophenyl)-3–(4-nitrophenyl)prop-2-en-1-one
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1
17.9, 110.2, 101.6. EI-MS (m/z): calculated 286.0, observed White crystals, yield ¼ 61%, m.p. ¼ 162–166 C. H NMR (700 MHz,
þ
86.0 (M ).
Chloroform-d) d 8.37–8.28 (m, 2H), 8.15–7.96 (m, 2H), 7.96–7.78
1
3
(
(
1
2
m, 3H), 7.64 (d, J ¼ 15.8 Hz, 1H), 7.59–7.45 (m, 2H).
176 MHz, CDCl ) d 188.3, 148.7, 142.0, 140.8, 139.9, 135.8, 130.0,
29.2, 129.0, 125.1, 124.3. EI-MS (m/z): calculated 287.0, observed
C NMR
3
7
. (E)-3-(benzo[d][1,3]dioxol-4-yl)-1–(3-bromophenyl)prop-2-en-1-one
ꢁ
1
þ
Yellow crystals, yield ¼ 67%, m.p. ¼ 107–111 C. H NMR
600 MHz, Chloroform-d) d 8.17 (s, 1H), 7.98 (d, J ¼ 7.0 Hz, 1H),
.84–7.65 (m, 3H), 7.47–7.35 (m, 1H), 7.04 (s, 1H), 6.90 (s, 2H), 6.16
87.0 (M ).
(
7
1
3
(
d, J ¼ 5.5 Hz, 2H). C NMR (150 MHz, CDCl
3
) d 189.1, 148.0, 146.8, 14. (E)-1-(benzo[d][1,3]dioxol-5-yl)-3–(4-fluorophenyl)prop-2-en-1-one
ꢁ
1
1
1
3
40.1, 140.0, 135.6, 131.5, 130.2, 127.0, 123.9, 123.5, 122.9, 122.0, White crystals, yield ¼ 58%, m.p. ¼ 126–130 C. H NMR (700 MHz,
17.7, 110.2, 101.6. EI-MS (m/z): calculated 331.9, observed Chloroform-d) d 7.80 (d, J ¼ 15.4 Hz, 1H), 7.75–7.61 (m, 3H),
þ
31.9 (M ).
7.61–7.51 (m, 1H), 7.43 (d, J ¼ 15.6 Hz, 1H), 7.20–7.07 (m, 2H), 6.93