Med Chem Res (2013) 22:3969–3983
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(C-300and C-500), 129.09 (C-200and C-600), 125.85(C-30),
122.57 (C-2) and 111.03 (C-40).
(E)-3-(3-Methoxyphenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-
one (8) MS: M? at m/z 227. Anal. Calcd for C14H13NO2:
C, 73.99; H, 5.77; N, 6.16 %. Found: C, 74.02; H, 5.81; N,
5.27 %. 1H NMR (400 MHz, CDCl3): d 3.84 (s, 3H,
OCH3), 6.33 (m, 1H, H-40), 6.94 (dd, 1H, J = 8.00 Hz and
2.04 Hz, H-400), 7.04 (m, 1H, H-30), 7.10 (d, 1H,
J = 2.04 Hz, H-200), 7.26 (d, 1H, J = 7.79 Hz, H-600), 7.44
(dd, 1H, J = 8.00 Hz and 7.79 Hz, H-500), 7.32 (d, 1H,
J = 16.00 Hz, H-2), 7.64 (d, 1H, J = 1.6 Hz, H-50), 7.79
(d, 1H, J = 16.00 Hz, H-3), 10.55 (s, 1H, NH). 13C NMR
(100 MHz, CDCl3): 179.06 (C-1), 159.94 (C-300), 142.21,
(C-3), 136.46 (C-100), 133.16 (C-20), 129.90 (C-50), 125.97
(C-30), 122.47 (C-500), 120.99, (C-2) 116.99 (C-600), 115.95
(C-400), 113.47 (C-40), 110.94 (C-200) and 55.34 (OCH3).
(E)-3-(4-Dimethylaminophenyl)-1-(1H-pyrrol-2-yl)prop-2-
en-1-one (12) MS: M? at m/z 240. Anal. Calcd for
C15H16N2O: C, 74.97; H, 6.71; N, 11.66 %. Found: C,
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75.85; H, 6.78; N, 11.68 %. H NMR (500 MHz, CDCl3):
d 3.05 (s, 6H, –N(CH3)2), 6.33 (m, 1H, H-40), 6.70 (d, 2H,
J = 8.8 Hz, H-300 & H-500), 7.03 (m, 1H, H-30), 7.05 (m,
1H, H-50), 7.17 (d, 1H, J = 15 Hz, H-2), 7.54 (d, 2H,
J = 8.8 Hz, H-200 and H-600), 7.79 (d, 1H, J = 15.5, H-3),
9.55 [s, 1H, H-10 (–NH)]. 13C NMR (125 MHz, CDCl3): d
179.35 (C-1), 151.85 (C-400), 143.07 (C-3), 133.58 (C-20),
130.15 (C-200 and C-600), 124.54 (C-50), 122.89 (C-100),
116.90 (C-30), 115.26 (C-2), 111.89 (C-300 and C-500),
110.62 (C-40), 40.14 (–N(CH3)2).
(E)-3-(2-Bromophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one
(9) MS: M? at m/z 276. Anal. Calcd for C13H10BrNO: C,
73.99; H, 5.77; N, 6.16 %. Found: C, 74.12; H, 5.78; N,
5.17 %. 1H NMR (400 MHz, CDCl3): d 6.35 (m, 1H,
H-40), 7.09 (m, 1H, H-400), 7.17 (m, 1H, H-30), 7.28 (d, 1H,
J = 16.00 Hz, H-2), 7.35 (d, 1H, J = 8.70 Hz, H-600), 7.40
(d, 1H, J = 1.68 Hz, H-50), 7.62 (dd, 1H, J = 8.70 Hz and
1.60 Hz, H-500), 7.74 (dd, 1H, J = 8.70 Hz and 1.60 Hz,
H-300), 8.18 (d, 1H, J = 16.00 Hz, H-3), 10.5 (bs, 1H, NH).
13C NMR (100 MHz, CDCl3): 178.59 (C-1), 140.61 (C-3),
135.21 (C-100), 133.48 (C-400), 132.98 (C-20), 131.00 (C-300),
127.82 (C-600), 127.64 (C-500), 126.17 (C-50), 125.74 (C-2),
125.04 (C-30), 117.01 (C-200) and 111.04 (C-40).
(E)-3-(2,6-Dimethoxyphenyl)-1-(1H-pyrrol-2-yl)prop-2-en-
1-one (13) MS: M? at m/z 257. Anal. Calcd for
C15H15NO3: C, 70.02; H, 5.88; N, 5.44 %. Found: C,
70.16; H, 5.92; N, 6.55 %. 1H NMR (500 MHz, CDCl3): d
3.82 (s, 6H, (–OCH3)2), 6.35 (m, 1H, H-40), 6.91 (d, 1H,
J = 16.48 Hz, H-2), 6.94 (dd, 1H, J = 3.02 Hz and
5.9 Hz, H-30), 7.07 (m, 2H, H-300 and H-500), 7.16 (t, 1H,
J = 3.2 Hz, H-50), 7.42 (d, 1H, J = 16.48 Hz, H-3), 8.08
(dd, 1H, J = 8.00 Hz, H-400), 9.65 (s, 1H, NH). 13C NMR
(125 MHz, CDCl3): d 178.56 (C-1), 150.87 (C-200and
C-600), 143.48 (C-3), 135.76 (C-400), 133.17 (C-20), 129.80
(C-50), 125.96 (C-30), 123.87(C-2), 111.98 (C-40), 110.60
(C-100), 109.98 (C-300 and C-500), 55.95 (OCH3), 55.56
(OCH3).
(E)-3-(4-Fluorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one
(10) MS: M? at m/z 215. Anal. Calcd for C13H10FNO: C,
72.55; H, 4.68; N, 6.51 %. Found: C, 72.65; H, 4.72; N,
6.59 %. 1H NMR (400 MHz, CDCl3): d 6.34 (m, 1H,
H-40), 7.06 (d, 1H, J = 2.03 Hz, H-30), 7.10 (m, 2H, H-300
and H-500), 7.16 (m, 1H, H-50), 7.30 (d, 1H, J = 15.66 Hz,
H-2), 7.59 (m, 2H, H-200 and H-600), 7.80 (d, 1H,
(E)-3-(2-Chloro-5-nitrophenyl)-1-(1H-pyrrol-2-yl)prop-2-
en-1-one (14) MS: M? at m/z 276.5. Anal. Calcd for
C13H9ClN2O3: C, 56.43; H, 3.28; N, 10.13 %. Found: C,
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56.56; H, 3.32; N, 10.43 %. H NMR (500 MHz, DMSO-
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d6): d 6.33 (m, 1H, H-40), 7.25 (s, 1H, H-30), 7.55 (s, 1H,
H-50), 7.84 (d, 1H, J = 8.8 Hz, H-300), 7.90 (d, 1H,
J = 15.5 Hz, H-2), 8.02 (d, 1H, J = 15.5 Hz, H-3), 8.22
(dd, 1H, J = 2.5 and 8.0 Hz, H-400), 8.93 (d, 1H,
J = 2.5 Hz, H-600). 13C NMR (125 MHz, DMSO-d6): d
176.70 (C-1), 146.85 (C-500), 140.14 (C-3), 134.01 (C-100),
133.41 (C-200), 132.80 (C-20), 131.30 (C-300), 128.32 (C-50),
127. 31 (C-600), 125.19 (C-30), 122.77 (C-2), 118.72 (C-400),
110.39 (C-40).
J = 15.66 Hz, H-3), 10.62 (bs, 1H, NH). C NMR
(100 MHz, CDCl3): 178.81 (C-1), 165.10 (C-400), 145.01
(C-3), 135.94 (C-20), 133.12 (C-100), 130.21 (C-200), 130.21
(C-600), 126.08 (C-50), 121.90 (C-30), 121.88 (C-2), 116.81
(C-300), 116.11 (C-500).
(E)-3-(4-Chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one
(11) MS: M? at m/z 213.5. Anal. Calcd for C13H10ClNO:
C, 67.39; H, 4.35; N, 6.05 %. Found: C, 67.34; H, 4.38; N,
6.13 %. 1H NMR (400 MHz, CDCl3): d 6.36 (m, 1H,
H-40), 7.07 (m, 1H, H-30), 7.12 (m, 1H, H-50), 7.31 (d, 1H,
J = 15.69 Hz, H-2), 7.54 (d, 2H, J = 8.0 Hz, H-300 and
H-500), 7.59 (d, 2H, J = 8 Hz, H-200 and H-600), 7.75 (d, 1H,
J = 15.6 Hz, H-3), 9.73 [bs, 1H, H-10 (NH)]. 13C NMR
(100 MHz, CDCl3): 178.67 (C-1), 140.79 (C-3), 136.04 (C-
400), 133.56 (C-100), 133.08 (C-20), 132.94 (C-50), 129.17
(E)-3-(2-Chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one
(15) MS: M? at m/z 231.5. Anal. Calcd for C13H10ClNO:
C, 67.39; H, 4.35; N, 6.05 %. Found: C, 67.55; H, 4.36; N,
6.08 %. 1H NMR (500 MHz, CDCl3): d 6.35 (m, 1H,
H-40), 7.10 (m, 1H, H-400), 7.11 (s, 1H, H-500), 7.18 (s, 1H,
H-30), 7.30 (m, 2H, H-300 and H-600), 7.34 (d, 1H,
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