BULLETIN OF THE
Article
Synthesis and Cytotoxicity Evaluation of Pyrrole Derivatives
KOREAN CHEMICAL SOCIETY
CDCl3) δ (ppm): 8.34–8.04 (m, 2H, ArH + CH ), 7.88 (d,
J = 9.0 Hz, 2H, ArH), 7.87–7.68 (m, 3H, ArH + CH ),
7.64–7.47 (m, 1H, ArH), 7.01 (d, J = 9.0 Hz, 2H, ArH),
3.82 (s, 3H, OCH3).
(m, 2H, ArH + CH ), 7.15–7.97 (m, 3H, ArH + CH ),
6.92 (d, J = 8.0 Hz, 2H, ArH), 3.85 (s, 3H, OCH3), 2.44 (s,
3H, PhCH3), 2.38 (s, 3H, PhCH3).
[4-(4-Methoxyphenyl)-1H-pyrrol-3-yl] (2, 4-dimethyl-
phenyl) methanone (3h). White solid, yield 93.9 %, mp
[4-(4-Methoxyphenyl)-1H-pyrrol-3-yl]
(3-bromo-
203–205 C. 1H NMR (300 MHz, DMSO-d6) δ (ppm):
ꢀ
phenyl) methanone (3e). White solid, yield 81.7 %, mp
215–217 C. 1H NMR (300 MHz, DMSO-d6) δ (ppm):
11.51 (s, 1H, pyrrole-NH), 7.40 (d, J = 9.0 Hz, 2H, ArH),
7.24 (d, J = 9.0 Hz, 1H, ArH), 7.06 (s, 1H, ArH), 7.02 (dd,
J1 = 9.0 Hz, J2 = 3.0 Hz, 1H, ArH), 6.95 (t, J = 3.0 Hz,
1H, pyrrole H), 6.89 (t, J = 3.0 Hz, 1H, pyrrole H), 6.85 (d,
J = 9.0 Hz, 2H, ArH), 3.75 (s, 3H, OCH3), 2.30 (s,
3H, PhCH3), 2.22 (s, 3H, PhCH3); 13C NMR (100 MHz,
DMSO d6) δ (ppm): 192.14, 157.59, 138.59, 138.57,
135.14, 131.08, 129.63 (2C), 129.23, 127.88, 127.54,
125.44, 124.88, 121.87, 119.41, 113.02 (2C), 54.97, 20.79,
19.33; ESI-HRMS m/z: calcd for C20H19NO2 ([M + H]):
306.1495; found: 306.1259.
ꢀ
11.64 (s, 1H, pyrrole–NH), 7.80–7.55 (m, 3H, ArH),
7.51–7.37 (m, 1H, ArH), 7.28 (d, J = 9.0 Hz, 2H, ArH),
7.25 (dd, J1 = 3.0 Hz, J2 = 0.9 Hz, 1H, pyrrole H), 7.00 (t,
J = 3.0 Hz, 1H, pyrrole H), 6.83 (d, J = 9.0 Hz, 2H, ArH),
3.73 (s, 3H, OCH3); 13C NMR (100 MHz, DMSO-d6) δ
(ppm): 118.61, 157.57, 142.24, 133.93, 131.27, 130.34,
129.50 (2C), 128.43, 127.82, 127.39, 125.23, 121.44,
120.00, 119.23, 113.17 (2C), 54.96; ESI-HRMS m/z: calcd
for C18H14BrNO2 ([M + H]): 356.0287, 358.0266; found:
356.0163, 358.0192.
3-(4-Methoxyphenyl)-1-(4-bromophenyl) propen-1-one
(2f ). Pale yellow solid, yield 93.5%. 1H NMR
(300 MHz, CDCl3) δ (ppm): 8.07 (d, J = 9.0 Hz, 2H, ArH),
7.85 (d, J = 9.0 Hz, 2H, CH ), 7.75 (d, J = 6.0 Hz, 4H,
ArH), 6.99 (d, J = 9.0 Hz, 2H, ArH), 3.80 (s, 3H, OCH3).
3-(4-Methoxyphenyl)-1-(3-methoxo-phenyl) propen-1-
one (2i). Pale yellow solid, yield 96.5%. 1H
NMR (300 MHz, CDCl3) δ (ppm): 7.81 (d, J = 15.0 Hz,
1H, CH ), 7.62 (d, J = 9.0 Hz, 2H, ArH), 7.60–7.50 (m,
2H, ArH + CH ), 7.46–7.35 (m, 2H, ArH), 7.13 (dd,
J1 = 9.0 Hz, J2 = 3.0 Hz, 1H, ArH), 6.95 (d, J = 9.0 Hz,
2H, ArH), 3.90 (s, 3H, OCH3), 3.87 (s, 3H, OCH3).
[4-(4-Methoxyphenyl)-1H-pyrrol-3-yl]
(4-bromo-
phenyl) methanone (3f ). White solid, yield 93.9 %, mp
250–252 C. 1H NMR (300 MHz, DMSO-d6) δ (ppm):
[4-(4-Methoxyphenyl)-1H-pyrrol-3-yl]
(3-methoxo-
ꢀ
11.62 (s, 1H, pyrrole–NH), 7.63 (s, 4H, ArH), 7.28 (d,
J = 9.0 Hz, 2H, ArH), 7.21 (dd, J1 = 3.0 Hz, J2 = 0.9 Hz,
1H, pyrrole H), 6.99 (t, J = 3.0 Hz, 1H, pyrrole H), 6.82 (d,
J = 9.0 Hz, 2H, ArH), 3.72 (s, 3H, OCH3); 13C NMR
(100 MHz, DMSO-d6) δ (ppm): 189.16, 157.55, 139.11,
131.11 (2C), 130.89 (2C), 129.46 (2C), 128.23, 127.45,
125.18, 125.13, 120.06, 119.13, 113.17 (2C), 54.96; ESI-
HRMS m/z: calcd for C18H14BrNO2 ([M + H]): 356.0287,
358.0266; found: 356.0203, 358.0199.
phenyl) methanone (3i). Pale yellow solid, yield 93.4 %,
1
ꢀ
mp 193–195 C. H NMR (300 MHz, DMSO-d6) δ (ppm):
11.56 (s, 1H, pyrrole–NH), 7.41–7.29 (m, 3H, ArH), 7.30
(d, J = 9.0 Hz, 2H, ArH), 7.32–7.26 (m, 2H, 1 pyrrole H
+1 ArH), 7.12 (m, 1H, ArH), 6.99 (t, J = 3.0 Hz, 1H, pyrrole
H), 6.82 (d, J = 9.0 Hz, 2H, ArH), 3.77 (s, 3H, OCH3), 3.73
(s, 3H, OCH3); 13C NMR (100 MHz, DMSO-d6) δ (ppm):
189.92, 158.86, 157.50, 141.51, 129.43 (2C), 129.20,
128.01, 127.62, 125.16, 121.36, 120.32, 118.99, 117.37,
113.57, 113.14 (2C), 55.12, 54.95; ESI-HRMS m/z: calcd
for C19H17NO3 ([M + H]): 308.1287; found: 308.1203.
3-(4-Methoxyphenyl)-1-(4-methoxo-phenyl) propen-1-
one (2j). Pale yellow solid, yield 94.2%. 1H NMR
(300 MHz, CDCl3) δ (ppm): 8.16 (d, J = 9.0 Hz, 2H, ArH),
7.83 (d, J = 18.0 Hz, 1H, CH ), 7.82 (d, J = 9.0 Hz, 2H,
3-(4-Methoxyphenyl)-1-(4-methylphenyl)
propen-1-
1
one (2g). White solid, yield 94.7%. H NMR (400 MHz,
CDCl3) δ (ppm): 7.93 (d, J = 8.0 Hz, 2H, ArH), 7.78 (d,
J = 16.0 Hz, 1H, CH ), 7.50 9 (d, J = 9.0 Hz, 2H, ArH),
7.42 (d, J = 16.0 Hz, 1H, CH ), 7.30 (d, J = 8.0 Hz, 2H,
ArH), 6.94 (d, J = 8.0 Hz, 2H, ArH), 3.86 (s, 3H, OCH3),
2.44 (s, 3H, PhCH3).
ArH), 7.68 (d, J = 18.0 Hz, 1H,
CH ), 7.09 (d,
[4-(4-Methoxyphenyl)-1H-pyrrol-3-yl]
(4-methyl-
J = 9.0 Hz, 2H, ArH), 7.02 (d, J = 9.0 Hz, 2H, ArH), 3.87
phenyl) methanone (3g). White solid, yield 81.3 %, mp
(s, 3H, OCH3), 3.82 (s, 3H, OCH3).
[4-(4-Methoxyphenyl)-1H-pyrrol-3-yl]
215–217 C. 1H NMR (300 MHz, DMSO-d6) δ (ppm):
(4-methoxo-
ꢀ
11.52 (s, 1H, pyrrole-NH), 7.65 (d, J = 9.0 Hz, 2H, ArH),
7.27 (t, J = 6.0 Hz, 4H, ArH), 7.16 (dd, J1 = 3.0 Hz,
J2 = 1.2 Hz, 1H, pyrrole H), 6.98 (t, J = 3.0 Hz, 1H, pyrrole
H), 6.83 (d, J = 9.0 Hz, 2H, ArH), 3.73 (s, 3H, OCH3), 2.36
(s, 3H, PhCH3); 13C NMR (100 MHz, DMSO-d6) δ (ppm):
190.03, 157.46, 141.48, 129.35 (2C), 129.11 (2C), 128.65
(2C), 127,70, 127.51, 125.08, 120.46, 118.81, 113.17 (2C),
54.94, 21.01; ESI-HRMS m/z: calcd for C19H17NO2
([M + H]): 292.1338; found: 292.1012.
phenyl) methanone (3j). White solid, yield 93.3 %, mp
203–205 C. 1H NMR (300 MHz, DMSO-d6) δ (ppm):
ꢀ
11.50 (s, 1H, pyrrole–NH), 7.75 (d, J = 9.0 Hz, 2H, ArH),
7.27 (d, J = 9.0 Hz, 2H, ArH), 7.17 (dd, J1 = 3.0 Hz,
J2 = 0.9 Hz, 1H, pyrrole H), 6.99 (dd, J1 = 3.0 Hz,
J2 = 0.9 Hz, 1H, pyrrole H), 7.00–6.98 (m, 1H, pyrrole H),
6.82 (d, J = 9.0 Hz, 2H, ArH), 3.82 (s, 3H, OCH3), 3.73
(s, 3H, OCH3); 13C NMR (100 MHz, DMSO-d6) δ (ppm):
189.26, 162.00, 157.40, 132.42, 131.24 (2C), 129.23 (2C),
127.75, 126.72, 124.98, 120.55, 118.55, 113.35 (2C),
113.20 (2C), 55.33, 54.93; ESI-HRMS m/z: calcd for
C19H17NO3 ([M + H]): 308.1287; found: 308.1212.
3-(4-Methoxyphenyl)-1-(2, 4-dimethyl phenyl) propen-
1
1-one (2h). White solid, yield 91.8%. H NMR (300 MHz,
CDCl3) δ (ppm): 7.52 (d, J = 9.0 Hz, 2H, ArH), 7.50–7.39
Bull. Korean Chem. Soc. 2016, Vol. 37, 200–206
© 2016 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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