Structural and stereochemical requirements of the spiroketal group of hippuristanol for antiproliferative activity.
Hippuristanol is a natural product that has recently been shown to inhibit eukaryotic translation initiation and tumor cell proliferation. To investigate the structure and activity relationship of hippuristanol, we synthesized a series of analogs by expanding the size of its F ring and determined their effects on the proliferation of cancer cell lines. All changes to the F-ring of hippuristanol resulted in 3-fold to >100-fold decrease in activity.
Li
Wei
W
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032 Shanghai, China.
Dang
Yongjun
Y
Liu
Jun O
JO
Yu
Biao
B
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005663:Furans / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013261:Sterols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D005663:Furans; D013141:Spiro Compounds; D013261:Sterols; C510125:hippuristanol; C520774:spiroketal
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