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R
¼
n-C
3
H
7
(
þ
)-calanolide E
24
26
R
¼
CH
3
(
þ
)-cordatolide E
16
27
C
6
H
5
O
COOH
O
OH
O
R
2
R
1
(VIII)
R
1
¼
CH
3
,R
2
¼
H calophyllic acid
9
28
R
1
¼
H, R
2
¼
CH
3
isocalophyllic acid
9
29
CH
3
O
O
MeO
O
O
(IX)
oblongulide
12,13
30
Scheme 8-1.
(Continued )
8.2
ANTI-HIV-1 ACTIVITY OF CALOPHYLLUM COUMARINS
8.2.1
Anti-HIV-1 Activity of Calanolides
8.2.1.1 Anti-HIV-1 Activity of Calanolides in Cell Culture
Flavin et al.
25
reported on the anti-HIV-1 activity of synthetic (
)-calanolide A and
resolved (
þ
)-calanolide A (1) and (
)-calanolide A [(
)-1] against both strains and
clinical isolates of HIV-1 shown in Table 8-1. The cytotoxicity in the different cell
lines examined of the (
)-1,(
þ
)-1, and (
)-calanolide A was approximately the
same levels. However, only (
þ
)-1 exhibited HIV-1 activity, which was similar to
the data reported for the natural product [(
þ
)-calanolide A, (1)],
8
and (
)-1 was
inactive. Both the AZT-resistant strain G910-6 and the pyridinone-resistant
strain A17 were inhibited by (
)-1 and (
þ
)-1.
8,25,26
The (
þ
)-1 was more active
than (
)-1 against the AZT-resistant strain G910-6 with an EC
50
value of
0.027 and 0.108 mM, respectively. It was interesting that the activity of (
)-1
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