busra arvas, *omer tahir gunkara, and nuket ocal
TRANSCRIPT
General Papers ARKIVOC 2018, vii, S1-S24
Page S1 ©ARKAT USA, Inc
Supplementary Material
Synthesis of arylpiperazine substituted bisindolylmethanes as possible pharmacologically active new compounds
Busra Arvas, Omer Tahir Gunkara, and Nuket Ocal *
Yildiz Technical University, Faculty of Science and Arts, Department of Chemistry, Davutpasa Campus, 34220,
Esenler, Istanbul, Turkey Email: [email protected]
Table of Contents
New bisindolylmethanes list ...................................................................................................................... S2-S4
IR, 1H-NMR, 13C-NMR, Qtof or LCMS spectra of new compounds .......................................................... S5-S24
General Papers ARKIVOC 2018, vii, S1-S24
Page S2 ©ARKAT USA, Inc
Entry Compound Name Compound Structure
3 3,3’-((4-Chlorophenyl)methylene)bis(1-(4-
bromobutyl)-1H-indole)
4 3,3’-((4-Fluorophenyl)methylene)bis(1-(4-
bromobutyl)-1H-indole)
5 3,3’-(Phenanthren-9-ylmethylene)bis(1-(4-
bromobutyl)-1H-indole)
6 3,3’-(Naphthalen-2-ylmethylene)bis(1-(4-
bromobutyl)-1H-indole)
11 1-(4-Bromobutyl)-3-((4-chlorophenyl)(1-(4-
(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl)-
1H-indol-3-yl)methyl)-1H-indole
General Papers ARKIVOC 2018, vii, S1-S24
Page S3 ©ARKAT USA, Inc
12
1-(4-Bromobutyl)-3-((1-(4-(4-(2,3-
dichlorophenyl)piperazin-1-yl)butyl)-1H-
indol-3-yl)(phenanthren-9-yl)methyl)-1H-
indole
13
1-(4-Bromobutyl)-3-((1-(4-(4-(2,3-
dichlorophenyl)piperazin-1-yl)butyl)-1H-indol-3-yl)(naphthalen-2-yl)methyl)-1H-
indole
14 1-(4-Bromobutyl)-3-((4-chlorophenyl)(1-(4-
(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1H-
indol-3-yl)methyl)-1H-indole
15 1-(4-Bromobutyl)-3-((4-fluorophenyl)(1-(4-
(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1H-
indol-3-yl)methyl)-1H-indole
General Papers ARKIVOC 2018, vii, S1-S24
Page S4 ©ARKAT USA, Inc
17 3,3’-(Phenylmethylene)bis(1-(4-(4-(3-
8trifluoromethyl)phenyl)piperazin-1-
yl)butyl)-1H-indole
General Papers ARKIVOC 2018, vii, S1-S24
Page S5 ©ARKAT USA, Inc
Compound 3
IR Spectrum of Compound 3
1H NMR spectrum of Compound 3
52
6.2
65
38
.67
56
0.4
95
71
.20
59
1.1
96
46
.25
67
1.8
67
02
.73
73
6.9
87
98
.80
85
9.2
19
25
.60
96
2.1
61
01
3.4
91
04
1.0
81
08
8.1
31
12
2.7
11
15
5.3
611
99
.80
12
18
.73
12
51
.57
12
63
.74
13
34
.01
13
59
.16
13
93
.40
14
65
.86
14
87
.58
15
47
.12
16
11
.25
17
32
.71
19
77
.54
20
32
.092
16
0.0
8
28
72
.18
29
37
.60
30
46
.16
BD-7 2-14 arasi
30
35
40
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60
65
70
75
80
85
90
%T
1000 1500 2000 2500 3000 3500 4000
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S6 ©ARKAT USA, Inc
13C NMR spectrum of Compound 3
QTof Spectrum of Compound 3
General Papers ARKIVOC 2018, vii, S1-S24
Page S7 ©ARKAT USA, Inc
Compound 4
IR spectrum of Compound 4
1H-NMR spectrum of Compound 4
60
6.2
46
38
.156
71
.80
73
7.3
37
83
.84
80
5.4
88
57
.269
26
.21
95
9.6
91
01
3.6
91
03
7.4
61
09
2.7
01
12
2.6
81
15
4.1
41
21
6.6
11
25
2.0
51
29
2.5
01
33
4.3
31
36
0.6
513
93
.57
14
65
.81
14
79
.47
15
04
.31
15
47
.05
16
01
.52
16
68
.09
17
09
.21
19
78
.46
20
34
.13
21
60
.81
28
51
.63
29
22
.99
30
46
.76
bd11t
60
65
70
75
80
85
90
95
%T
1000 1500 2000 2500 3000 3500 4000
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S8 ©ARKAT USA, Inc
APT spectrum of Compound 4
LCMS Spectrum of Compound 4
General Papers ARKIVOC 2018, vii, S1-S24
Page S9 ©ARKAT USA, Inc
Compound 5
IR spectrum of Compound 5
1H-NMR spectrum of Compound 5
61
5.8
06
61
.22
70
1.2
47
28
.85
74
7.5
17
96
.03
86
4.4
291
0.8
11
01
5.3
410
81
.6112
58
.99
13
36
.61
13
62
.161
39
5.3
71
44
6.0
31
46
5.2
11
54
5.2
91
61
0.0
41
65
4.1
017
24
.30
19
78
.46
20
29
.00
21
61
.02
28
51
.53
29
21
.17
29
61
.62
bd14t
45
50
55
60
65
70
75
80
85
90
95
%T
1000 1500 2000 2500 3000 3500 4000
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S10 ©ARKAT USA, Inc
13C NMR spectrum of Compound 5
LCMS Spectrum of Compound 5
General Papers ARKIVOC 2018, vii, S1-S24
Page S11 ©ARKAT USA, Inc
Compound 6
IR spectrum of Compound 6
1H-NMR spectrum of Compound 6
73
9.1
47
66
.27
77
8.6
28
04
.07
83
0.9
68
48
.89
86
2.7
49
00
.26
90
9.9
29
28
.33
94
8.0
79
61
.83
10
10
.85
10
30
.80
10
43
.10
10
71
.67
10
96
.82
11
25
.42
11
55
.18
11
70
.81
11
96
.31
12
20
.12
12
48
.41
12
69
.22
12
90
.78
13
33
.04
13
59
.80
13
95
.80
14
34
.93
14
44
.12
14
66
.80
14
78
.92
15
06
.32
15
49
.421
60
1.1
31
61
0.8
316
32
.79
16
47
.13
17
30
.72
17
68
.42
18
88
.12
19
22
.39
19
78
.31
20
28
.29
21
60
.81
28
77
.30
29
40
.74
30
48
.41
31
26
.42
BD15
50
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65
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80
85
90
95
%T
1000 1500 2000 2500 3000 3500 4000
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S12 ©ARKAT USA, Inc
APT spectrum of Compound 6
LCMS Spectrum of Compound 6
General Papers ARKIVOC 2018, vii, S1-S24
Page S13 ©ARKAT USA, Inc
Compound 11
IR Spectrum of Compound 11
1H-NMR spectrum of Compound 11
64
8.2
46
72
.12
71
3.7
07
33
.71
78
0.6
28
00
.21
85
9.6
59
07
.28
96
1.0
71
01
3.7
01
04
4.5
61
05
8.8
21
08
8.2
11
10
1.3
51
13
7.1
11
15
4.9
711
99
.48
12
40
.36
12
82
.17
13
34
.38
13
64
.38
13
93
.81
14
21
.23
14
47
.05
14
65
.63
14
87
.66
15
48
.22
15
77
.15
16
11
.65
17
14
.92
19
79
.24
21
61
.14
22
42
.90
28
18
.77
28
73
.29
29
32
.03
30
47
.34
BD-8 tekrar
30
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85
90
%T
1000 1500 2000 2500 3000 3500 4000
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S14 ©ARKAT USA, Inc
APT spectrum of Compound 11
QTof spectrum of Compound 11
General Papers ARKIVOC 2018, vii, S1-S24
Page S15 ©ARKAT USA, Inc
Compound 12
IR spectrum of Compound 12
1H-NMR spectrum of Compound 12
61
6.9
46
29
.64
64
4.8
16
71
.92
71
3.5
67
26
.69
74
0.3
27
80
.86
82
4.0
89
05
.87
95
8.1
11
01
3.2
41
04
3.8
5
11
36
.29
11
54
.64
11
68
.78
12
00
.39
12
39
.83
13
03
.40
13
35
.22
13
63
.03
14
21
.86
14
48
.41
14
65
.16
14
94
.28
15
49
.79
15
77
.5216
11
.29
16
75
.70
17
32
.23
19
77
.81
20
28
.42
21
60
.15
23
23
.74
28
50
.79
29
22
.01
30
52
.89
33
35
.88
BD-16
86
87
88
89
90
91
92
93
94
95
96
97
98
%T
1000 1500 2000 2500 3000 3500
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S16 ©ARKAT USA, Inc
APT spectrum of Compound 12
QTof Spectrum of Compound 12
General Papers ARKIVOC 2018, vii, S1-S24
Page S17 ©ARKAT USA, Inc
Compound 13
IR spectrum of Compound 13
1H-NMR spectrum of Compound 13
61
8.9
66
46
.75
67
3.4
57
11
.86
73
8.2
57
66
.41
77
8.4
78
06
.52
86
3.5
29
23
.3894
5.5
39
61
.54
10
12
.831
04
3.5
811
36
.46
11
83
.35
12
40
.41
14
08
.14
15
72
.04
19
77
.65
20
33
.97
21
60
.58
28
50
.80
29
26
.45
30
01
.71
33
34
.61
BD-17
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%T
1000 1500 2000 2500 3000 3500
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S18 ©ARKAT USA, Inc
APT spectrum of Compound 13
QTof Spectrum of Compound 13
General Papers ARKIVOC 2018, vii, S1-S24
Page S19 ©ARKAT USA, Inc
Compound 14
IR spectrum of Compound 14
1H-NMR spectrum of Compound 14
73
7.5
27
95
.89
86
0.4
79
35
.61
95
6.7
99
82
.511
01
3.2
71
03
9.7
21
08
7.8
01
12
1.9
41
15
3.1
81
17
3.7
91
23
9.9
21
25
7.5
41
28
5.8
11
30
6.5
11
33
3.6
51
35
7.6
81
39
1.5
11
44
5.3
91
46
6.3
01
48
7.5
81
54
5.6
01
58
3.7
01
61
0.9
0
17
32
.66
19
77
.44
20
29
.51
21
60
.29
28
10
.28
28
52
.19
29
27
.37
30
45
.11
32
66
.87
BD10
78
80
82
84
86
88
90
92
94
96
98
100
%T
1000 1500 2000 2500 3000 3500 4000
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S20 ©ARKAT USA, Inc
APT spectrum of Compound 14
MS Spectrum
QTof Spectrum of Compound 14
General Papers ARKIVOC 2018, vii, S1-S24
Page S21 ©ARKAT USA, Inc
Compound 15
IR spectrum of Compound 15
1H-NMR spectrum of Compound 15
73
7.1
47
83
.30
79
6.6
18
34
.52
86
3.7
39
56
.58
98
2.5
910
13
.89
10
43
.17
10
84
.17
11
21
.07
11
53
.75
11
74
.21
12
17
.90
12
57
.42
12
91
.16
13
06
.92
13
34
.88
13
57
.58
13
91
.98
14
45
.99
14
66
.33
14
80
.39
15
04
.61
15
46
.27
15
83
.99
17
32
.49
19
77
.95
20
30
.73
21
60
.57
28
10
.85
28
53
.23
29
32
.9930
45
.99
33
69
.10
BD-12
25
30
35
40
45
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70
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80
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95
%T
1000 1500 2000 2500 3000 3500 4000
Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S22 ©ARKAT USA, Inc
APT spectrum of Compound 15
QTof Spectrum of Compound 15
General Papers ARKIVOC 2018, vii, S1-S24
Page S23 ©ARKAT USA, Inc
Compound 17
IR spectrum of Compound 17
1H-NMR spectrum of Compound 17
53
1.4
55
50
.55
60
3.5
16
67
.90
69
5.0
874
0.9
07
82
.17
82
4.2
88
48
.46
94
8.8
79
91
.93
10
44
.48
10
75
.73
11
21
.3311
82
.43
12
33
.22
12
89
.51
13
09
.35
13
50
.27
14
52
.0514
94
.14
16
09
.96
16
98
.96
20
30
.29
21
61
.02
23
59
.37
29
23
.49
29
66
.53
J-232
40
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95
100
105
%T
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Wavenumbers (cm-1)
General Papers ARKIVOC 2018, vii, S1-S24
Page S24 ©ARKAT USA, Inc
APT spectrum of Compound 17
QTof Spectrum of Compound 17