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S1
Supplementary Information for
Microwave-assisted one-pot synthesis of steroid-quinoline hybrids and
an evaluation of their antiproliferative activity on gynecological cancer
cell lines
Ádám Baji,
a, ‡ András Gyovai,
b, ‡ János Wölfling,
a Renáta Minorics,
b, Imre Ocsovszki,
c, István
Zupkó,b,
* Éva Franka,*
aDepartment of Organic Chemistry, University of Szeged, Dóm tér 8., Szeged H-6720, Hungary
bDepartment of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6., Szeged H-
6720, Hungary
cDepartment of Biochemistry, University of Szeged, Dóm tér 9, Szeged H-6720, Hungary
E-mail: [email protected]; [email protected]
Table of Contents
Representative NMR spectra of the synthesized compounds S2-S26
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2016
S2
ppm (t1)
0.05.010.0
10
.02
7.1
9
7.1
8
6.7
4
6.7
3
6.7
2
6.7
2
6.6
5
3.7
8
2.9
1
2.9
0
1.0
0
1.0
0
0.9
90
.96
0.8
8
3.0
5
2.1
2
2
O
H
H H
Cl
H
O
ppm (t1)050100150
18
8.0
16
2.4
15
7.6
13
7.7
13
6.4
13
1.8
12
5.9
11
3.8
11
1.6
55
.2
53
.0
51
.0
44
.0
37
.2
33
.0
29
.5
28
.2
27
.0
25
.9
15
.2
2
S3
ppm (t1)
0.01.02.03.04.05.06.07.08.0
8.1
1
8.1
0
7.9
1
7.7
4
7.7
3
7.6
5
7.6
3
7.6
1
7.4
8
7.4
6
7.4
5
7.2
9
7.2
7
6.7
7
6.7
6
6.7
5
6.7
5
6.6
9
3.8
0
1.1
0
1.0
00
.97
1.0
2
0.9
9
1.0
01
.02
1.0
0
0.9
9
3.0
4
3.0
5
5a
O
H
H H
N
1'
2'
3' 4'
4a' 5'
6'
7'8'
8a'
ppm (t1)
050100150
17
4.4
15
7.5
14
7.3
13
7.7
13
4.9
13
2.5
13
1.0
12
8.9
12
8.2
12
7.6
12
7.5
12
6.2
12
5.4
11
3.9
11
1.5
55
.2
54
.6
46
.1
44
.3
37
.9
33
.8
30
.0
29
.7
27
.5
26
.4
17
.7
5a
S4
ppm (f1)
0.01.02.03.04.05.06.07.08.0
8.0
4
8.0
2
7.8
3
7.5
0
7.4
7
7.4
6
7.2
8
7.2
7
6.7
6
6.7
4
6.6
8
3.8
0
2.5
1
1.0
9
0.9
91
.03
0.9
5
0.9
81
.03
1.0
0
0.9
6
3.1
3
3.1
1
1.0
2
5.1
3
1.1
9
1.0
7
4.2
3
1.1
1
3.1
3
O
H
H H
N
5b
ppm (f1)
050100150
17
3.3
15
7.5
13
7.7
13
5.2
13
4.9
13
2.5
13
0.8
13
0.8
13
0.5
12
8.2
12
7.6
12
6.5
12
6.2
11
3.9
11
1.5
55
.2
54
.6
46
.0
44
.3
37
.8
33
.8
29
.9
29
.7
27
.4
26
.4
21
.4
17
.6
S5
ppm (f1)
0.01.02.03.04.05.06.07.08.0
8.0
4
8.0
2
7.8
3
7.3
0
7.3
0
7.2
8
7.2
6
7.0
4
7.0
3
6.7
6
6.7
4
6.7
4
6.6
8
6.6
7
3.9
1
3.7
9
1.0
8
1.0
01
.01
1.0
1
2.2
4
0.9
9
0.9
6
3.0
73
.12
3.1
0
1.0
5
2.0
8
1.0
7
1.0
4
4.2
1
1.0
9
3.1
3
O
H
H H
NOMe
5c
ppm (f1)
050100150
17
1.9
15
7.5
15
7.1
13
7.7
13
5.3
13
2.5
13
0.4
13
0.3
12
9.9
12
8.5
12
6.2
12
0.2
11
3.9
11
1.4
10
5.9
55
.5
55
.2
54
.7
45
.9
44
.3
37
.8
33
.8
30
.0
29
.7
27
.4
26
.3
17
.7
S6
ppm (t1)
0.01.02.03.04.05.06.07.08.0
8.4
8
8.4
6
8.0
2
8.0
1
7.7
7
7.3
0
7.3
0
7.2
8
7.2
8
7.0
0
7.0
0
6.9
6
6.9
6
6.9
5
6.9
4
6.7
8
6.7
8
3.9
1
3.8
7
3.0
9
3.0
7
3.0
6
2.9
7
2.9
6
2.9
4
1.0
0
0.9
8
1.0
4
1.0
2
1.0
51
.07
1.0
4
3.2
03
.26
2.1
72
.16
9d
O
1
2
3
4 5
6
7
8
4a
12a
N7a
9
1011
11a
6a12
O
ppm (t1)
050100150
16
0.6
15
7.3
15
1.1
14
0.7
13
2.5
13
0.4
13
0.3
12
8.3
12
7.3
12
1.0
11
2.9
10
4.8
55
.5
55
.3
28
.9
28
.7
9c
S7
ppm (t1)0.01.02.03.04.05.06.07.08.09.0
8.6
4
8.6
2
7.8
6
7.7
4
7.7
3
7.6
3
7.6
1
7.3
5
7.3
3
7.3
1
6.9
8
6.9
8
6.9
7
6.9
6
6.7
8
6.7
7
3.8
8
3.1
3
3.1
1
3.1
0
2.9
9
2.9
8
2.9
6
1.0
0
1.0
1
1.0
2
1.0
20
.95
1.0
1
0.9
7
3.1
5
2.1
32
.14
9e
O
1
2
3
4 5
6
7
8
4a
12a
N7a
9
1011
11a
6a12
Cl
ppm (t1)050100150
16
1.2
15
3.9
14
3.6
14
1.2
13
3.8
13
3.3
13
0.8
12
8.7
12
8.7
12
8.4
12
7.5
12
5.9
12
5.4
11
3.2
11
2.8
55
.3
28
.6
28
.5
9d
S8
ppm (t1)
0.01.02.03.04.05.06.07.08.0
8.4
9
8.4
7
8.0
3
8.0
1
7.7
6
7.6
7
7.6
7
7.5
6
7.5
6
7.5
4
7.5
4
6.9
7
6.9
6
6.9
5
6.9
4
6.7
8
6.7
8
3.8
7
3.1
0
3.0
8
3.0
7
2.9
8
2.9
6
2.9
5
1.0
0
1.0
2
1.0
00
.99
1.0
3
0.9
7
0.9
8
3.1
4
2.0
92
.18
9f
O
1
2
3
4 5
6
7
8
4a
12a
N7a
9
10
11
11a
6a12
Cl
ppm (t1)
050100150
16
1.1
15
3.6
14
1.2
13
2.5
13
1.1
13
1.0
13
0.6
12
9.4
12
8.0
12
7.8
12
7.3
12
5.5
11
3.1
11
2.9
55
.3
28
.8
28
.5
9e
S9
ppm (t1)
0.01.02.03.04.05.06.07.08.09.0
8.4
9
8.4
7
7.9
7
7.9
5
7.8
5
7.8
5
7.7
5
7.6
9
7.6
8
7.6
7
7.6
7
6.9
6
6.9
6
6.9
5
6.9
4
6.7
8
6.7
8
3.8
7
3.1
0
3.0
9
3.0
7
2.9
8
2.9
6
2.9
5
1.0
0
0.9
91
.02
1.0
31
.01
1.0
3
1.0
2
3.1
8
2.1
22
.20
9g
O
1
2
3
4 5
6
7
8
4a
12a
N7a
9
1011
11a
6a12
Br
ppm (t1)
050100150
16
0.8
15
3.4
14
0.9
13
2.1
13
1.6
13
0.6
13
0.3
12
8.5
12
8.2
12
7.5
11
8.9
11
2.8
11
2.6
55
.0
28
.4
28
.2
9f
S10
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.9
8
7.9
6
7.7
9
7.7
0
7.6
8
7.6
1
7.6
0
7.5
8
7.4
4
7.4
2
7.4
1
4.6
2
3.1
0
3.0
9
3.0
7
3.0
6
2.9
9
2.9
5
2.8
1
2.7
9
2.7
8
2.7
5
2.6
1
2.5
8
2.1
8
2.1
7
2.1
7
2.1
5
2.0
5
0.8
2
0.8
0
1.0
0
1.0
2
0.9
8
1.0
11
.01
1.0
2
0.9
91
.02
1.0
1
1.0
1
0.9
93
.05
6.2
7
13a
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
ppm (t1)
050100150
17
1.2
15
8.3
14
6.6
13
5.8
13
0.0
12
8.5
12
8.2
12
7.2
12
6.8
12
5.5
82
.8
53
.5
50
.7
43
.5
42
.5
42
.2
37
.3
36
.9
35
.3
31
.1
28
.6
27
.5
23
.5
21
.2
20
.8
12
.0
11
.6
13a
S11
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.8
7
7.7
1
7.4
4
7.4
3
4.6
4
4.6
2
4.6
0
3.0
8
3.0
5
3.0
4
2.9
6
2.9
3
2.8
0
2.7
7
2.7
6
2.7
3
2.5
9
2.5
6
2.4
9
2.0
5
0.8
2
0.7
9
1.0
0
1.9
7
1.0
1
0.9
8
0.9
4
1.0
0
0.9
7
0.9
73
.05
13b
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'8'
8a'
ppm (t1)
050100150
17
1.2
15
7.2
13
5.4
13
5.3
13
1.0
13
0.0
12
7.7
12
7.2
12
5.6
82
.8
53
.5
50
.7
43
.5
42
.5
42
.2
37
.1
36
.9
35
.3
35
.3
31
.1
28
.6
27
.5
23
.5
21
.5
21
.2
20
.8
12
.01
1.6
13b
S12
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.8
7
7.8
5
7.6
8
7.2
7
7.2
7
7.2
6
7.2
5
7.2
5
6.9
5
6.9
5
4.6
4
4.6
2
4.6
0
3.8
9
3.0
5
3.0
4
3.0
1
3.0
0
2.9
5
2.9
2
2.7
7
2.7
4
2.7
3
2.7
1
2.5
8
2.5
5
2.0
5
0.8
1
0.7
9
1.0
0
3.0
3
0.9
7
1.0
0
1.2
4
0.9
8
1.9
9
0.9
9
1.0
0
13d
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
MeO
ppm (t1)
050100150
17
1.2
15
7.1
15
5.5
14
6.5
13
4.7
13
0.3
12
9.6
12
8.0
12
1.3
10
4.3
82
.8
55
.4
53
.5
50
.7
43
.5
42
.5
42
.2
37
.0
36
.9
35
.3
31
.1
28
.6
27
.5
23
.5
21
.2
20
.8
12
.0
11
.6
13c
S13
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.8
0
7.7
1
7.7
0
7.6
2
7.6
0
7.3
4
7.3
3
7.3
1
4.6
4
4.6
2
4.6
0
3.2
2
3.2
1
3.1
9
3.1
8
2.9
9
2.9
6
2.9
0
2.8
7
2.8
6
2.8
4
2.6
0
2.5
7
2.1
9
2.1
8
2.1
7
2.1
6
2.1
5
2.0
5
0.8
1
0.7
9
1.0
6
0.9
6
1.0
21
.00
1.0
0
1.1
43
.26
1.0
10
.94
1.0
2
1.0
5
13e
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
Cl
ppm (t1)
050100150
17
1.2
15
9.6
14
2.8
13
6.1
13
2.3
13
1.1
12
8.5
12
8.5
12
6.0
12
5.3
82
.7
53
.4
50
.7
43
.3
42
.5
42
.1
37
.5
36
.9
35
.3
35
.2
31
.1
28
.4
27
.5
23
.5
21
.2
20
.8
12
.01
1.7
13d
S14
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.9
0
7.8
9
7.7
0
7.6
6
7.6
6
7.5
3
7.5
3
7.5
2
7.5
1
4.6
4
4.6
2
4.6
1
3.0
7
3.0
6
3.0
4
3.0
3
2.9
8
2.9
5
2.7
9
2.7
6
2.7
5
2.7
2
2.6
0
2.5
7
2.0
5
0.8
2
0.7
9
1.0
0
0.9
6
1.0
00
.93
0.9
1
1.0
83
.06
0.9
9
1.0
0
1.0
10
.99
6.0
31
.07
1.1
01
.04
13f
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
Cl
ppm (t1)
050100150
17
1.2
15
8.7
14
4.9
13
4.8
13
1.1
13
1.1
12
9.8
12
9.4
12
7.8
12
5.4
82
.7
53
.4
50
.7
43
.5
42
.5
42
.1
37
.2
36
.9
35
.3
35
.3
31
.1
28
.5
27
.5
23
.5
21
.2
20
.8
12
.01
1.7
13e
S15
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.8
3
7.8
2
7.6
9
7.6
6
7.6
6
7.6
4
7.6
4
4.6
4
4.6
2
4.6
1
3.0
7
3.0
5
3.0
3
3.0
2
2.9
8
2.9
5
2.7
7
2.7
5
2.7
4
2.7
1
2.6
0
2.5
7
2.2
1
2.2
0
2.1
9
2.1
8
2.1
7
2.1
7
2.1
5
2.1
5
2.1
3
2.0
5
0.8
2
0.7
9
1.0
0
1.9
20
.98
0.9
7
1.0
01
.03
1.0
1
1.0
1
1.0
43
.03
13g
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
Br
ppm (t1)
050100150
17
1.2
15
8.9
14
5.2
13
4.7
13
1.9
13
1.1
13
0.0
12
8.8
12
8.3
11
9.2
82
.7
53
.4
50
.7
43
.5
42
.5
42
.1
37
.3
36
.9
35
.3
35
.3
31
.1
28
.5
27
.5
23
.5
21
.2
20
.8
12
.11
1.7
13f
S16
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.9
6
7.7
6
7.6
2
7.6
0
7.3
8
7.3
8
7.3
6
7.3
6
4.6
4
4.6
2
4.6
0
3.0
7
3.0
6
3.0
3
3.0
2
2.9
6
2.9
3
2.7
8
2.7
6
2.7
5
2.7
2
2.5
7
2.5
4
2.1
9
2.1
8
2.1
7
2.1
6
2.1
5
2.1
4
2.0
5
2.0
3
0.8
1
0.7
8
1.0
0
0.9
81
.00
0.9
9
0.9
9
1.0
23
.03
0.8
6
1.0
1
0.9
8
0.9
3
13h
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'Cl
ppm (t1)
050100150
17
1.2
15
9.5
14
6.9
13
5.6
13
4.2
13
0.4
12
8.0
12
7.3
12
6.5
12
5.5
82
.7
53
.4
50
.7
43
.4
42
.5
42
.1
37
.3
36
.9
35
.3
31
.1
28
.5
27
.5
23
.5
21
.2
20
.8
12
.0
11
.7
13g
S17
ppm (t1)
0.01.02.03.04.05.06.07.08.0
8.2
0
7.9
0
7.9
0
7.8
9
7.8
8
7.5
1
7.5
0
7.5
0
4.6
4
4.6
3
4.6
1
3.1
0
3.0
9
3.0
7
3.0
5
3.0
4
2.8
1
2.7
9
2.7
7
2.7
5
2.6
4
2.6
1
2.2
0
2.1
8
2.1
8
2.1
7
2.1
6
2.1
5
2.0
5
0.8
2
0.8
0
1.0
0
0.9
3
0.9
1
1.8
7
1.9
8
0.9
9
0.9
9
1.0
03
.05
13'h
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
Cl
ppm (t1)050100150
17
1.2
15
9.2
13
2.6
13
1.3
13
0.4
12
8.2
12
7.5
12
5.5
12
5.3
82
.7
53
.4
50
.7
43
.6
42
.5
42
.1
37
.1
36
.9
35
.3
31
.1
28
.5
27
.5
23
.5
21
.2
20
.8
12
.1
11
.7
13g'
S18
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.7
5
7.5
4
7.5
3
7.4
5
7.4
4
7.3
3
7.3
1
7.3
0
4.6
4
4.6
3
4.6
1
3.1
4
3.1
3
3.1
0
3.0
9
2.9
8
2.9
5
2.8
4
2.8
2
2.8
1
2.7
8
2.6
0
2.5
7
2.2
0
2.1
9
2.1
8
2.1
7
2.1
6
2.0
6
0.8
2
0.8
11
.00
0.9
6
0.9
8
0.9
7
1.0
3
0.9
0
0.9
9
3.9
5
1.0
0
0.9
83
.00
13c
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
ppm (t1)
050100150
17
1.2
15
7.2
13
6.0
13
5.9
13
2.1
12
9.6
12
8.5
12
7.1
12
5.2
12
4.9
82
.8
53
.5
50
.7
43
.5
42
.5
42
.3
37
.6
36
.9
35
.4
31
.2
28
.6
27
.5
23
.5
21
.2
20
.8
18
.0
12
.01
1.7
13h
S19
ppm (f1)
0.01.02.03.04.05.06.07.08.09.0
7.9
5
7.8
3
7.8
1
7.7
5
7.7
3
7.5
8
7.5
6
7.4
9
7.4
7
7.4
6
7.4
6
7.2
6
7.2
5
4.6
2
4.6
1
4.6
0
3.0
7
3.0
6
3.0
3
3.0
2
3.0
2
2.9
8
2.9
4
2.9
1
2.7
8
2.7
5
2.7
2
2.6
2
2.5
9
2.5
6
2.5
1
2.0
4
0.8
1
0.7
7
13i 13'i
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'8'
8a'
H
H
H H
O
O
N1'
2'
3'4'
4a'5'
6'
7'8'
8a'
ppm (t1)
050100150
17
1.2
15
8.1
14
6.9
13
8.6
13
5.5
13
3.6
13
2.4
12
9.5
12
9.1
12
8.2
12
7.8
12
7.2
12
6.5
12
6.4
12
6.0
12
5.3
82
.8
53
.4
50
.7
43
.4
42
.5
42
.2
42
.1
37
.3
37
.2
36
.9
35
.3
35
.3
31
.1
28
.6
27
.5
23
.5
21
.8
21
.2
20
.81
2.0
11
.6
13i 13i'
S20
ppm (f1)
0.01.02.03.04.05.06.07.08.0
7.9
9
7.9
7
7.8
0
7.7
0
7.6
8
7.6
2
7.6
0
7.5
9
7.4
4
7.4
3
7.4
1
3.6
7
3.1
1
3.1
0
3.0
7
3.0
6
3.0
0
2.9
7
2.8
2
2.8
0
2.7
9
2.7
6
2.6
1
2.5
8
2.0
9
2.0
8
2.0
7
2.0
7
2.0
6
0.8
0
0.7
8
14a
H
H
H H
OH
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.8
9
7.8
7
7.7
0
7.4
4
7.4
2
3.6
8
3.6
6
3.6
4
3.0
8
3.0
7
3.0
5
3.0
4
2.9
7
2.9
4
2.7
9
2.7
7
2.7
6
2.7
3
2.5
8
2.5
5
2.4
9
0.7
9
0.7
7
1.0
0
1.0
01
.05
1.0
5
1.1
43
.38
1.0
6
1.0
6
1.1
5
1.0
1
1.0
2
1.9
6
14b
H
H
H H
OH
N1'
2'
3'4'
4a'5'
6'
7'8'
8a'
14b
14a
S21
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.8
8
7.7
8
7.7
7
7.2
9
7.2
8
7.1
4
3.9
0
3.5
7
3.5
5
3.5
4
2.9
6
2.9
3
2.8
9
2.6
8
2.6
6
2.6
2
2.4
4
2.4
1
0.7
4
0.7
3
1.0
0
1.0
4
1.0
21
.14
3.1
1
1.0
2
2.0
3
1.0
0
0.9
9
14d
H
H
H H
OH
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
MeO
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.7
9
7.7
1
7.7
0
7.6
2
7.6
0
7.3
4
7.3
2
7.3
1
3.6
8
3.6
6
3.6
4
3.2
2
3.2
1
3.1
8
3.1
7
3.0
0
2.9
7
2.9
0
2.8
8
2.8
6
2.8
4
2.6
0
2.5
7
2.0
8
0.8
0
0.7
71
.00
1.0
10
.96
1.0
6
1.0
1
1.0
1
1.0
21
.03
1.0
2
1.0
9
14e
H
H
H H
OH
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
Cl
14c
14d
S22
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.9
1
7.8
9
7.6
9
7.6
6
7.5
3
7.5
2
3.6
8
3.6
7
3.6
5
3.0
7
3.0
6
3.0
3
3.0
2
2.9
9
2.9
6
2.7
9
2.7
6
2.7
5
2.7
3
2.5
9
2.5
6
0.7
9
0.7
8
1.0
0
2.0
6
1.0
2
1.0
3
1.2
3
1.0
1
2.0
2
0.9
3
14f
H
H
H H
OH
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
Cl
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.8
4
7.8
3
7.6
9
7.6
6
7.6
5
3.6
8
3.6
7
3.6
5
3.0
6
3.0
5
3.0
3
3.0
2
2.9
9
2.9
5
0.7
9
0.7
7
1.0
0
1.0
1
1.0
1
1.0
50
.98
1.9
20
.97
0.9
3
14g
H
H
H H
OH
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
Br
14e
14f
S23
ppm (t1)
0.01.02.03.04.05.06.07.08.0
7.9
7
7.7
6
7.6
2
7.6
1
7.3
8
7.3
6
3.6
8
3.6
6
3.6
5
3.0
7
3.0
6
3.0
3
3.0
2
2.9
7
2.9
4
2.7
9
2.7
7
2.7
5
2.7
3
2.5
7
2.5
4
0.7
9
0.7
7
1.0
0
0.9
9
1.0
10
.95
0.9
7
0.9
3
0.9
80
.96
0.8
2
14h
H
H
H H
OH
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'Cl
ppm (t1)
0.01.02.03.04.05.06.07.08.0
8.2
0
7.9
0
7.8
9
7.5
0
3.6
7
3.6
5
3.1
0
3.0
9
3.0
8
3.0
6
3.0
5
2.8
1
2.7
9
2.7
8
2.7
5
2.6
4
2.6
0
0.8
0
0.7
8
1.0
0
2.0
3
1.0
2
1.0
3
1.9
0
0.9
5
0.9
8
14'h
H
H
H H
OH
N1'
2'
3'4'
4a'5'
6'
7'
8'8a'
Cl
14g
14g'
S24
ppm (f1)0.01.02.03.04.05.06.07.08.0
7.7
7
7.5
5
7.5
3
7.4
6
7.4
4
7.3
3
7.3
2
7.3
0
3.6
6
3.6
5
3.6
3
3.1
6
3.1
3
2.9
9
2.9
5
2.8
6
2.8
3
2.8
2
2.7
9
2.5
9
2.5
6
0.8
1
0.7
7
1.0
00
.98
1.0
6
0.9
8
1.0
0
0.8
9
1.0
2
4.1
0
1.0
6
1.1
8
1.0
3
5.4
8
9.8
9
1.1
82
.04
8.3
4
H
H
H H
OH
N
14h
S25
ppm (t1)
0.05.010.0
11
.99
11
.97
8.1
9
8.1
7
7.1
0
7.0
7
7.0
4
7.0
2
4.6
3
4.6
1
4.6
0
2.4
3
2.4
0
2.3
7
2.3
6
2.3
3
2.3
2
2.2
3
2.2
0
2.1
7
2.1
6
2.1
4
2.1
3
2.1
2
2.0
9
2.0
4
0.8
2
0.8
1
1.0
6
0.9
3
2.0
0
1.0
02
.04
2.0
7
3.3
03
.46
H
N
HO
H
H
H
OAc
15
NO2
ppm (t1)
050100150200
20
1.4
17
1.2
14
6.2
14
2.2
13
9.4
12
6.0
11
4.7
10
8.2
82
.7
53
.1
50
.7
42
.5
42
.4
42
.3
41
.7
36
.9
35
.7
35
.3
31
.0
28
.2
27
.5
23
.5
21
.2
20
.81
2.0
11
.5
S26
HSQC spectrum of compound 15:
HMBC spectrum of compound 15:
ppm (t2)
0.05.010.0
0
50
100
150
ppm (t1)
ppm (t2)
5.010.0
50
100
150
200
ppm (t1)
