Computational Study of Shuangancistrotectorine A …
185
25
24
23
30
29
26
22
21
28
27
31
32
33
39
40
38
34
35
36
N
37
13
12
11
20
19
14
18
17
16
15
5
6
7
10
9
4
8
1
2
N
3
58
H
63
O
56
CH 3
H 3
59
C
57 CH 3
46
O
O
44
54
H
O
45
H 3
55
C
43
O
42
O
52 H
51 CH 3
41
O
61
O
H 3
62
C
H
48
49 CH 3
47 CH 3
64 CH 3
H 3
60
C
50 CH 3
H 3
53 C
A
B
C
D'
C'
B'
A'
D
Fig. 1 Structure of the shuangancistrotectorine A molecule and atom numbering utilized in this
work. The C atoms in the rings are denoted by the numbers showing their positions. Only the H
atoms attached to O or N are numbered separately, while the H atoms attached to a C atom are given
the same number as that C atom
Besides the conformational preferences, energetics and relevant geometric characteristics such as the parameters of the IHBs, all the other computable molecular
properties (dipole moments, HOMO-LUMO gaps, solvent effect, etc.) are also considered and analysed. In addition, comparisons are made with the results of the studies
of other dimeric NIQ alkaloids: jozimine A 2 [3] (JZM, another C 2 -symmetric NIQ
alkaloid with antimalarial activity [7]) and michellamine A [5] (MCA, a naphthylisoquinoline alkaloid with anti-HIV activity [8]). The three molecules differ by the substituents in the moieties and by the fact that the two naphthalene moieties in MCA
are not identical, while they are identical in JZM and SHA (fig. S1). Comparison of
the stabilising factors of the three molecules is given particular attention.
185
25
24
23
30
29
26
22
21
28
27
31
32
33
39
40
38
34
35
36
N
37
13
12
11
20
19
14
18
17
16
15
5
6
7
10
9
4
8
1
2
N
3
58
H
63
O
56
CH 3
H 3
59
C
57 CH 3
46
O
O
44
54
H
O
45
H 3
55
C
43
O
42
O
52 H
51 CH 3
41
O
61
O
H 3
62
C
H
48
49 CH 3
47 CH 3
64 CH 3
H 3
60
C
50 CH 3
H 3
53 C
A
B
C
D'
C'
B'
A'
D
Fig. 1 Structure of the shuangancistrotectorine A molecule and atom numbering utilized in this
work. The C atoms in the rings are denoted by the numbers showing their positions. Only the H
atoms attached to O or N are numbered separately, while the H atoms attached to a C atom are given
the same number as that C atom
Besides the conformational preferences, energetics and relevant geometric characteristics such as the parameters of the IHBs, all the other computable molecular
properties (dipole moments, HOMO-LUMO gaps, solvent effect, etc.) are also considered and analysed. In addition, comparisons are made with the results of the studies
of other dimeric NIQ alkaloids: jozimine A 2 [3] (JZM, another C 2 -symmetric NIQ
alkaloid with antimalarial activity [7]) and michellamine A [5] (MCA, a naphthylisoquinoline alkaloid with anti-HIV activity [8]). The three molecules differ by the substituents in the moieties and by the fact that the two naphthalene moieties in MCA
are not identical, while they are identical in JZM and SHA (fig. S1). Comparison of
the stabilising factors of the three molecules is given particular attention.