Microwave-Assisted Synthesis and Antitumor Activity of Salicyl Acyloxy Phosphonate Derivatives

doi:10.6023/cjoc201406026

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2566-2571.DOI: 10.6023/cjoc201406026 Previous Articles Next Articles

Notes

水杨酰氧基膦酸酯衍生物的微波辅助合成及抗肿瘤活性研究

杨家强^a, 马俊^a, 车万莉^a, 李明刚^a, 黎刚^a, 宋宝安^b

a. 遵义医学院药学院遵义 563003;
b. 贵州大学精细化工研究中心贵阳 550025

收稿日期:2014-06-18 修回日期:2014-07-17 发布日期:2014-08-11
通讯作者: 杨家强 E-mail:yjqcn@126.com
基金资助:
贵州省科技厅基金(No.黔科合外G字[2014]7013)﹑贵州省教育厅(No.黔科合人才团队字[2012]03号)资助项目.

Microwave-Assisted Synthesis and Antitumor Activity of Salicyl Acyloxy Phosphonate Derivatives

Yang Jiaqiang^a, Ma Jun^a, Che Wanli^a, Li Minggang^a, Li Gang^a, Song Baoan^b

a. School of Pharmacy, Zunyi Medical College, Zunyi 563003;
b. Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received:2014-06-18 Revised:2014-07-17 Published:2014-08-11
Supported by:
Project supported by the Technology Department of Guizhou Province (No. G[2014]7013), the Education Department of Guizhou Province (No. QJHRCTDZ-2012-03).

Twelve new salicyl acyloxy phosphonate derivatives were synthesized via microwave-assisted reactions of salicylic acid with α-hydroxyphosphonate in DCC/DMAP. The structures of the products were confirmed by elemental analysis, IR, ¹H NMR and ¹³C NMR data. The suitable synthetic conditions were as follows: in 15 mL of CH₂Cl₂ with power 800 W at room temperature for 3.5 h. The cytotoxic activities of all compounds on A-549, SGC-7901, HEp-2 and EC-109 in vitro were evaluated by using an 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method, and some of them showed good antitumor activity. Among the active compounds, espectively, compound 2f had better inhibition effect on HEp-2 cells growth [IC₅₀=(13.9±0.6) μmol/L], the IC₅₀ values of compound 2k was (8.5±0.9) μmol/L against EC-109 cells, similar to cisplatin [IC₅₀=(5.9±1.0) μmol/L].

Key words: salicylic acid, α-hydroxyphosphonate, microwave irradiation, synthesis, antitumor activity

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Yang Jiaqiang, Ma Jun, Che Wanli, Li Minggang, Li Gang, Song Baoan. Microwave-Assisted Synthesis and Antitumor Activity of Salicyl Acyloxy Phosphonate Derivatives[J]. Chin. J. Org. Chem., 2014, 34(12): 2566-2571.

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水杨酰氧基膦酸酯衍生物的微波辅助合成及抗肿瘤活性研究

Microwave-Assisted Synthesis and Antitumor Activity of Salicyl Acyloxy Phosphonate Derivatives

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