Stilbene Class Of Natural Products And Related Compounds Synthesis And Antitumor Activity Studies

As a group of stilbeneoids, dihydrostilbenes were considered to be important natural products. Recently some dihydrostilbenes were reported to be tubulin polymerization inhibitors and display potent antimitotic activity to a broad spectrum of human cancer lines.Because of its better antimitotic activity, a novel natural dihydrostilbenes 5-(2-(benzo[d] [1,3]dioxol-5-yl)ethyl)-7-methoxybenzo[d][1,3]dioxol-4-ol (compound A) from Bulbophyllum odoratissimum had been synthesized before. However, there were some drawbacks in the preparation such as the use of dangerous regents, cumbersome isolation procedures and low yield. In our effort to overcome those above mentioned shortcomings, a new route was applied to synthesize compound A. The yield was increased from 5.1% to 5.6% and the product was identified by ~1H-NMR and MS which were consistent with the sample of the natural product.Dihydrostilbenes are rare sorts in the nature. Up to now we selected six fragments from known antimitotic activity dihydrostilbenes to synthesize three analogs 6-methoxy-5-(3,4,5-rim-ethoxyphenethyl)benzo[d][1,3]dioxol-4-ol(compound3-1 ),5-(2-(7-hydroxybenzo[d][1,3]diox ol-5-yl)ethyl)-6-methoxybenzo[d][1,3]dioxol-4-ol(compound3-2),6-(2-(benzo[d][1,3] dioxol-5-yl) ethyl)-4-methoxybenzo[d][1,3] dioxole (compound 3-3). The compounds 3-1 and 3-2 exhibited significant cytotoxic activities against SGC-7901, KB and HT-1080 human cancer cell lines using the tetrazolium dye reduction assay (MTT assay).In searching for novel antitumor agents and understanding their structure-activity relationships. The fact that intermediate 4-(benzyloxy)- 7-methoxy -benzo[d] [1,3] dioxole -5-carbaldehyde (7) of the synthetic materials A showed antitumor activity occurred to us, so three analogs of compound 7 were synthesized to test their antitumor activities by MTT assay.