SUN Nannan, LIU Jia, ZHENG Canhui, ZHOU Youjun. Synthesis,XRD analysis and anti-tumor activity of novel compounds containing tetrahydronaphthalen-2-ol[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(3): 191-194. doi: 10.3969/j.issn.1006-0111.2014.03.007
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SUN Nannan, LIU Jia, ZHENG Canhui, ZHOU Youjun. Synthesis,XRD analysis and anti-tumor activity of novel compounds containing tetrahydronaphthalen-2-ol[J]. Journal of Pharmaceutical Practice and Service, 2014, 32(3): 191-194. doi: 10.3969/j.issn.1006-0111.2014.03.007
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Synthesis,XRD analysis and anti-tumor activity of novel compounds containing tetrahydronaphthalen-2-ol
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Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
- Received Date: 2014-03-25
- Rev Recd Date:
2014-04-11
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Abstract
Objective To synthesize the enantiomers of (E)-6-methoxy-1-(3,4,5-trimethoxybenzylidene)-1,2,3,4-tetrahydronaphthalen-2-ol,determine their structures by XRD and evaluate their anti-tumor activity in vitro. Methods The target compounds were prepared from 2,6-Dimethoxybenzoyl chloride. The key intermediate,(E)-6-methoxy-1-(3,4,5-trimethoxybenzylidene)-1,2,3,4-tetrahydronaphthalen-2-one,was obtained through Cornforth reduction and Knoevenael reaction,and the final R,S compounds were got by CBS asymmetric reduction.The structure of the target compounds were determined by XRD. The target compounds were rested by anti-tubulin and anti-tumor assay. Results The structure of the target compounds were determined by 1H NMR,13C NMR,MS,and XRD analysis.The yield of asymmetric reduction reaction was 90.3%,e.e.% was 99.04%,in vitro anti-tumor assay showed all of the S isomer had stronger anticancer activity than the R isomer,especially on CCRF-CEM cell(IC50=1 nmol/L),HCT-116 cell(IC50=0.14 μmol/L) and inhibition of tubulin polymerization (IC50=0.41 μmol/L). Conclusion The CBS asymmetric reduction was a good way to get high-yield and high optical purity compound. The S isomer with outstanding anticancer activity was worth further research.
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