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OO
OO
O
RNH
2
+
O
O
O
CH
3
OH
O
N
N
R
R
O
O
O
137
138
N
R= H, CH
3
, CH
2
CHMe
2
, CH
2
CH=CH
2
CH
2
CHO, CH
2
C
6
H
5
,
CH
2
CH
2
CH
2
O
,
S
,
Scheme 5-22
OO
OO
EWG
O
O
NaOH, THF
N
N
H
O
O
EWG
139
140
EWG = COOC
2
H
5
, CN, COCH
3
, SO
3
C
6
H
5
, SO
2
C
6
H
5
, SOC
6
H
5
Scheme 5-23
5.5.9
Carbaartemisinin
To inspect the effect of the segment of O-O-C-O-C-O-C
¼
O in the artemisinin
molecule, carbaartemisinin 141 and its analogs 142-144 (Structure 5-18) were
synthesized and evaluated. These compounds displayed much lower antimalarial
activity in vitro than artemisinin.
218
5.5.10
Steroidal Qinghaosu Derivatives
Some research groups synthesized steroidal qinghaosu derivatives in which the
qinghaosu nucleus, trioxane, or tetraoxane combined with a steroidal skeleton in
O O
O O
O O
O O
O
O
O
RO
O
R = H, Me, CH
2
Ph
141
142
143
144
Structure 5-18
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