Chemistry Reference
In-Depth Information
R
R
R
i
ii
O
OO
O
OO
HO
OO
R
R
iv
iii
O
OO
O
OO
OR′
OH
OR
′
OH
R=substitutents on coumarin
R
′
=camphonyl
i. 3-Chloro-3-methyl-1-butyne, K
2
CO
3
, KI, DMF/N
2
;
ii. N, N-diethylaniline, reflux;
iii. K
2
OsO
2
(OH)
4
, K
3
Fe(CN)
6
, DHQ-type ligan, K
2
CO
3
, ice-bath;
iv. Camphanoyl chloride, DMAP/CH
2
Cl
2
;
Scheme 9-1. General synthetic method for DCK analogs.
TABLE 9-2. Structures and Anti-HIV Activities of Monosubstituted
DCK Analogs (51-62)
a,25
5
4
6
3
O
O
O
O-camp
IC
50
(mM)
b
EC
50
(mM)
c
TI
d
No.
O-camp
2
:
56
10
4
1
:
37
10
5
DCK(2)
35.0
5
:
25
10
5
>
2
:
15
10
6
51
3-substitution
CH
3
>
113
2
:
38
10
3
>
6
:
43
10
4
52
OCH
3
>
153
1
:
83
10
6
>
6
:
89
10
7
53
4-substitution
CH
3
>
126
2
:
99
10
3
>
5
:
12
10
4
54
OCH
3
>
153
1
:
75
10
2
>
8
:
63
10
3
55
CH
2
CH
2
CH
3
>
151
3
:
15
10
2
>
4
:
79
10
3
56
CH(CH
3
)
2
>
151
>
1
:
19
10
3
57
C
6
H
5
>
143
0.12
58
CF
3
>
145
1.81
>
80.1
2
:
39
10
7
>
3
:
97
10
8
59
5-substitution
CH
3
>
95
1
:
92
10
4
>
7
:
97
10
5
60
OCH
3
>
153
61
6-substitution
CH
3
33
0.151
218
62
OCH
3
>
153
15.8
>
9.68
AZT
1875
0.045
41,667
a
Inhibitory of HIV-1 IIIB in H9 lymphocytes.
b
Concentration that inhibits uninfected H9 cell growth by 50%.
c
Concentration that inhibits viral replication by 50%.
d
Therapeutic Index, TI
¼
IC
50
=
EC
50
.
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