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Ethyl 2-[4-{bis(1H-indol-3-yl)methyl}-2-methoxyphenoxy]acetate
(3f)
Ethyl 2-[4-{bis(2-methyl-1H-indol-3-yl)methyl}phenoxy] propionate
(3l)
Pale pink solid; 78% yield; FT-IR (KBr): mmax 3385, 1743 cmꢁ1
;
pink solid; 72% yield; FT-IR (KBr): 3398, 3325, 1723 cmꢁ1 1H
;
1H NMR (300 MHz, CDCl3): 1.23 (t, J = 12.3 Hz, 3H), 3.65 (s, 3H),
4.21 (q, J = 12.3 Hz, 2H), 4.60 (s, 2H), 5.77 (s, 1H), 6.45 (s, 2H),
6.61–7.34 (m, 13H), 7.89 (s, 2H); 13C NMR (75 MHz, CDCl3): 14.1,
39.7, 55.7, 61.2, 66.5, 111.1, 112.8, 113.8, 119.0, 119.4, 120.4,
121.7, 123.6, 126.9, 136.6, 138.5, 145.4, 149.2, 169.3; ESI-MS: m/z
453.2; Anal. Calcd. for C28H26N2O4: C, 73.99, H 5.77, N 6.16%.
Found: C, 74.03; H, 5.81; N, 6.21%.
NMR (300 MHz, CDCl3): 1.26 (t, J = 11.7 Hz, 3H), 1.98 (s, 6H), 2.75
(t, J = 12.6 Hz, 2H), 4.13–4.21 (m, 4H), 5.91 (s, 1H), 6.74–7.26 (m,
12H), 8.13 (s, 2H); 13C NMR (75 MHz, CDCl3): 12.2, 14.1, 34.7,
38.4, 60.6, 63.6, 110.0, 113.4, 114.3, 118.8, 119.2, 120.3, 128.9,
129.9, 131.9, 135.1, 136.4, 156.7, 171.1; ESI-MS: m/z 465.2; Anal.
Calcd. for C30H30N2O3: C, 77.23; H, 6.48; N, 6.00%. Found: C,
77.28; H, 6.46; N, 6.03%.
Ethyl 2-[4-{bis(1H-indol-3-yl)methyl}-2-methoxyphenoxy]propionate
(3g)
Ethyl 2-[4-{bis(2-methyl-1H-indol-3-yl)methyl}-2-methoxyphenoxy]
acetate (3m)
Pale pink solid; 78% yield; FT-IR (KBr): mmax 3414, 3370,
pink solid, 74% yield, FT-IR (KBr): 3419, 1736 cmꢁ1 1H NMR
;
1739 cmꢁ1
;
1H NMR (300 MHz, CDCl3): 1.22 (t, J = 12.6 Hz, 3H),
(300 MHz, CDCl3) d: 1.20 (t, J = 7.0 Hz, 3H), 2.03 (s, 6H), 4.25 (q,
J = 7.0 Hz, 2H), 4.59 (s, 2H), 5.92 (s, 1H), 6.76–7.24 (m, 11H), 7.72
(s, 2H); 13C NMR (75 MHz, CDCl3) d:12.3, 14.1, 38.4, 61.3, 65.7,
109.9, 113.5, 114.3, 119.0, 119.3, 120.5, 128.9, 130.0, 131.7,
135.0, 137.0, 156.1, 169.1; ESI-MS: m/z 481.2; Anal. Calcd. for
2.78 (t, J = 13.2 Hz, 2H), 3.66 (s, 3H), 4.12 (q, J = 12.6 Hz, 2H), 4.23
(t, J = 13.2 Hz, 2H), 5.78 (s, 1H), 6.51–7.36 (m, 13H), 7.87 (s, 2H);
13C NMR (75 MHz, CDCl3): 14.1, 34.6, 39.7, 55.8, 60.6, 64.7, 111.0,
112.9, 113.8, 119.0, 119.6, 119.8, 120.7, 121.7, 123.6, 126.9,
136.6, 137.7, 146.2, 149.2, 171.2; ESI-MS: 467.3; Anal. Calcd. for
C30H30N2O3: C, 74.67; H, 6.27; N, 5.81%. Found: C, 74.70; H, 6.26;
C29H28N2O4: C, 74.34; H, 6.02; N, 5.98%. Found: C, 74.39; H, 5.98;
N, 5.85%.
N, 5.93%.
Ethyl 2-[4-{bis(2-methyl-1H-indol-3-yl)methyl}-2-methoxyphenoxy]
propionate (3n)
Ethyl 2-[2-{bis(2-methyl-1H-indol-3-yl)methyl}phenoxy] acetate (3h)
pink solid, 82% yield; FT-IR (KBr): 3406, 3369, 1733 cmꢁ1
;
1H
pink solid, 78% yield; FT-IR (KBr): 3391, 1727 cmꢁ1 1H NMR
;
NMR (300 MHz, CDCl3): 1.18 (t, J = 14.4 Hz, 3H), 2.05 (s, 6H), 4.14
(q, J = 14.4 Hz, 2H), 4.39 (s, 2H), 6.33 (s, 1H), 6.72–7.23 (m, 12H),
7.68 (s, 2H); 13C NMR (75 MHz, CDCl3): 12.2, 14.1, 33.4, 60.9,
66.4, 109.8, 112.3, 113.1, 118.9, 119.3, 120.3, 121.5, 127.2, 129.3,
130.6, 131.7, 133.3, 135.0, 156.3, 169.3; ESI-MS: m/z 451.2; Anal.
Calcd. for C29H28N2O3: C, 76.97; H, 6.24; N, 6.19%. Found: C,
77.02; H, 6.20; N, 6.23%.
(300 MHz, CDCl3): 1.25 (t, J = 12.6 Hz, 3H), 2.33 (s, 6H), 2.83 (t,
J = 11.4 Hz, 2H) 3.65 (s, 3H), 4.16 (q, J = 12.6 Hz, 2H), 4.28 (t,
J = 11.4 Hz, 2H), 5.93 (s, 1H), 6.70–7.25 (m, 11H), 7.72 (s, 2H); 13C
NMR (75 MHz, CDCl3): 12.4, 14.2, 34.7, 38.8, 56.0, 60.7, 64.9,
109.9, 113.5, 113.9, 119.0, 119.3, 120.5, 128.9, 131.7, 135.0,
137.4, 146.2, 149.5, 171.2; ESI-MS: m/z 495.2; Anal. Calcd. for
C29H28N2O3: C, 74.98; H, 6.50; N, 5.64%. Found: C, 75.00; H, 6.56;
N, 6.60%.
Ethyl 2-[2-{bis(2-methyl-1H-indol-3-yl)methyl}phenoxy] propionate
(3i)
Methyl 2-(2-(di(1H-indol-3-yl)methyl)phenoxy)acetate (4a)
pink solid; 85% yield; FT-IR (KBr): 3395, 3383, 1713 cmꢁ1
;
1H
Pink solid, 72% yield, FT-IR (KBr): 3390, 1718 cmꢁ1 1H NMR
;
NMR (300 MHz, CDCl3): 1.26 (t, J = 14.4 Hz, 3H), 1.98 (s, 6H), 2.75
(t, J = 12.6 Hz, 2H), 4.13–4.21 (m, 4H), 5.91 (s, 1H), 6.74–7.26 (m,
12H), 8.13 (s, 2H); 13C NMR (75 MHz, CDCl3): 12.2, 14.1, 34.7,
38.4, 60.6, 63.6, 110.0, 113.4, 114.3, 118.8, 119.2, 120.3, 128.9,
129.9, 131.9, 135.1, 136.4, 156.7, 171.1; ESI-MS: m/z 465.2; Anal.
Calcd. for C30H30N2O3: C, 77.23; H, 6.48; N, 6.00%. Found: C,
77.26; H, 6.52; N, 5.97%.
(300 MHz, CDCl3): 3.70 (3H, s), 4.60 (2H, s), 6.43 (1H, s), 6.68–
7.46 (14H, m), 7.86 (2H, s); 13C NMR (75 MHz, CDCl3): 32.5, 51.8,
66.1, 110.8, 112.1, 119.0, 119.3, 120.0, 121.7, 123.5, 127.1, 127.2,
130.0, 133.3, 136.7, 155.4, 169.5; ESI-MS: m/z 409.2; Anal. Calcd.
for C26H22N2O3: C, 76.08; H, 5.40; N, 6.82%. Found: C, 76.05; H,
5.42; N, 6.84%.
Butyl 2-(2-(di(1H-indol-3-yl)methyl)phenoxy)acetate (4b)
Ethyl 2-[2-{bis(2-methyl-1H-indol-3-yl)methyl}-6-methoxyphenoxy]
acetate (3j)
Rosy solid, 64% yield, FT-IR (KBr): 3383, 1713 cmꢁ1 1H NMR
;
(300 MHz, CDCl3): 0.87 (3H, J = 14.7 Hz, t), 1.29 (2H, m), 1.56 (2H,
m), 4.13 (2H, J = 6.6 Hz, t), 4.57 (2H, s), 6.41 (1H, s), 6.60–7.44
(14H, m), 7.78 (2H, s); 13C NMR (75 MHz, CDCl3): 13.6, 18.9, 30.5,
32.4, 65.0, 66.0, 110.9, 111.8, 118.9, 119.2, 120.0, 121.5, 121.7,
127.2, 130.0, 133.1, 136.6, 155.3, 169.3 ESI-MS: m/z 451.1; Anal.
Calcd. for C29H28N2O3: C, 76.97; H, 6.24; N, 6.19%. Found: C,
76.92; H, 6.20; N, 6.23%. Compound (CCDC 882631) crystallizes
in the orthorhombic system, space group Pca2(1), with
a = 22.851(3) Å, b = 8.2624(9) Å, and c = 12.1785(14) Å, and
Pink solid; 65% yield; FT-IR (KBr): 3393, 3375, 1752 cmꢁ1 1H
;
NMR (500 MHz, CDCl3) d: 1.18 (t, J = 7.0 Hz, 3H), 2.07 (s, 6H),
3.79 (s, 3H), 3.94 (s, 2H), 4.04 (q, J = 7.0 Hz, 2H), 6.37 (s, 1H),
6.81–7.21 (m, 11H), 7.71 (s, 2H); 13C NMR (75 MHz, CDCl3) d:
12.24, 14.18, 33.70, 55.75, 60.51, 69.20, 109.90, 110.67, 113.11,
119.05, 119.43, 120.42, 122.39, 123.69, 129.11, 131.84, 135.01,
138.04, 145.75, 152.15, 169.65; ESI-MS m/z: 481.2; Anal. Calcd.
For C30H30N2O3: C, 74.67; H, 6.27; N, 5.18; Found C, 74.60; H,
6.21; N, 6.20.
a
= 90°, b = 90° and c T
= 90°, volume 2299.3(4) Å3, Z = 4,
= 110(2) K, 25,016 reflections measured, 5243 unique reflections,
with a Goodness-of-fit on F2 is 0.918, R1 = 0.0345, wR2 = 0.0879.
Ethyl 2-[4-{bis(2-methyl-1H-indol-3-yl)methyl}phenoxy] acetate (3k)
pink solid; 70% yield; FT-IR (KBr): 3419, 1736 cmꢁ1 1H NMR
;
(300 MHz, CDCl3): 1.25 (t, J = 12.3 Hz, 3H), 2.01 (s, 6H), 4.25 (q,
J = 12.3 Hz, 2H), 4.58 (s, 2H), 5.92 (s, 1H), 6.76–7.24 (m, 12H),
7.72 (s, 2H); 13C NMR (75 MHz, CDCl3): 12.3, 14.1, 38.4, 61.2,
65.7, 109.9, 113.5, 114.3, 119.0, 119.3, 120.5, 128.9, 130.0, 131.7,
135.0, 137.1, 156.2, 169.1; ESI-MS: m/z 451.2; Anal. Calcd. for
DPPH free radical scavenging activity
The free-radical scavenging activity of the compounds 3a–3l
was measured by the decrease in absorbance of methanolic solu-
tion of DPPH. A stock solution of DPPH (33 mg/l) was prepared in
methanol and 5 ml of this solution was added to 1 ml of each com-
C29H28N2O3: C, 76.97; H, 6.24; N, 6.19%. Found: C, 76.98; H, 6.26;
N, 6.22%.
pound at different concentrations (25, 50 lg/ml). After 30 min,