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Synthesis and antitumor activities of unsymmetrically disubstituted acylthioureas fused with hydrophenanthrene structure

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Abstract

A series of novel unsymmetrically disubstituted acylthioureas fused with hydrophenanthrene structure were synthesized from Δ8-dihydroabietic and dehydroabietic acid, respectively. Their structures were characterized by IR, 1H-, and 13C-NMR spectroscopy. The antitumor activities of the title compounds against SMMC7721 and A549 tumor cells were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) method. The results showed that three compounds (4c1, 4d1, and 4d2) exhibited highly effective activities against SMMC7721 and A549 cells, their IC50 values are between 1.87–12.67 μM for SMMC7721 cells and 2.20–6.79 μM for A549 cells, respectively. Structure–activity relationship indicating that acylthioureas that furan group fused with Δ8-dihydroabietyl group, trihydroxymethyl fused with Δ8-dihydroabietyl and dehydroabietyl could generate enhance activities of this kind of compounds against SMMC7721 and A549 cells.

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Acknowledgments

This research was financially supported by grants from National Natural Science Foundation of China (No. 30771690) and Forestry Commonwealth Industry Special Foundation of China (No. 200704008).

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Authors and Affiliations

  1. Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, 210042, People’s Republic of China

    Xiao-Ping Rao, Yong Wu, Zhan-Qian Song, Shi-Bin Shang & Zong-De Wang

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  1. Xiao-Ping Rao
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  2. Yong Wu
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  3. Zhan-Qian Song
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  4. Shi-Bin Shang
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  5. Zong-De Wang
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Correspondence to Xiao-Ping Rao.

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Rao, XP., Wu, Y., Song, ZQ. et al. Synthesis and antitumor activities of unsymmetrically disubstituted acylthioureas fused with hydrophenanthrene structure. Med Chem Res 20, 333–338 (2011). https://doi.org/10.1007/s00044-010-9303-8

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  • DOI: https://doi.org/10.1007/s00044-010-9303-8

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