TY - JOUR
T1 - Synthesis of amide analogs of arenastatin A
AU - Murakami, Nobutoshi
AU - Wang, Weiqi
AU - Ohyabu, Naoki
AU - Ito, Takeshi
AU - Tamura, Satoru
AU - Aoki, Shunji
AU - Kobayashi, Motomasa
AU - Kitagawa, Isao
N1 - Funding Information:
The authors are grateful to Dr K. Sugita, the Research Laboratory of Shionogi Pharmaceutical Co., Ltd., for in vivo anti-tumor test. The authors are also grateful to the Naito Foundation, the Houansha Foundation, and the Ministry of Education, Sciences, Sports, and Culture of Japan for financial support.
PY - 2000/11/10
Y1 - 2000/11/10
N2 - In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells.
AB - In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells.
KW - Cytotoxin
KW - Depsipeptide
KW - Marine metabolite
KW - Marine sponge
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U2 - 10.1016/S0040-4020(00)00766-3
DO - 10.1016/S0040-4020(00)00766-3
M3 - Article
AN - SCOPUS:0034634668
VL - 56
SP - 9121
EP - 9128
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 46
ER -