Synthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenes and their analogues.
A total synthetic route for two natural dihydrostilbenes with significant cytotoxicity toward human cancer cell lines, (3-(2-(7-methoxybenzo[d][1,3]dioxol-5-yl)ethyl)phenol 1a and 6-(3-hydroxyphenethyl)benzo[d][1,3]dioxol-4-ol 1b), which were isolated from Bulbophyllum odoratissimum Lindl, was developed via Wittig-Horner reaction. The natural products 1a and 1b were obtained in 28% and 20% overall yield, respectively. Additionally, nine analogues, 1c-1k, of the two natural dihydrostilbenes were synthesized and evaluated for their anti-proliferative activity against human SGC-7901, KB and HT-1080 cell lines by MTT assay. The activities of 1c and 1d were in the same range as those of the natural products 1a and 1b.
Zhang
Wei-Ge
WG
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, PR China. zhangweige2000@sina.com
Zhao
Rui
R
Ren
Jian
J
Ren
Li-Xiang
LX
Lin
Jin-Guang
JG
Liu
Dai-Lin
DL
Wu
Ying-Liang
YL
Yao
Xin-Sheng
XS
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D048588:Benzoxazines / Q000138:chemical synthesis / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D003124:Colorimetry; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D029595:Orchidaceae / Q000737:chemistry*; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
C520879:6-bromo-3-(4-butylphenyl)-1,3-benzoxazine-2,4-(3H)-dione; D000972:Antineoplastic Agents, Phytogenic; D048588:Benzoxazines; D013267:Stilbenes