橙酮衍生物的合成及初步抗肿瘤活性研究
收稿日期: 2013-05-20
修回日期: 2013-07-10
网络出版日期: 2013-08-12
基金资助
国家自然科学基金(Nos. 20872118，30070905)、陕西省重点实验室基金(Nos. 2010JS097，11JS090，12JS110)和陕西省教育厅基金(No. 12JK1010)资助项目.
Synthesis and Preliminary Antitumor Activities of Aurone Derivatives
Received date: 2013-05-20
Revised date: 2013-07-10
Online published: 2013-08-12
Supported by
Project supported by the National Natural Science Fundation of China (Nos. 20872118, 30070905), the Key Laboratory Fund of Shaanxi Province of China (Nos. 2010JS097, 11JS090, 12JS110) and the Foundation of the Education Department of Shaanxi Province (No. 12JK1010).
橙酮是黄酮类化合物中的重要一类，具有广泛的生物活性和药理作用，如抗肿瘤、抗炎、抗氧化、抗菌和对昆虫的拒食活性等. 由于其在自然界分布较少，且在植物体内的含量都很低，致使其提取分离成本高，较难大规模获得. 为了解决这一问题，同时进一步研究构效关系，以苯氧乙酸、2，3，5-三甲基苯酚、4-氯-3，5-二甲基苯酚、氯乙酸以及各种芳香醛为原料，通过三步反应设计合成了A环无取代橙酮、5-氯-4，6-二甲基橙酮及4，6，7-三甲基橙酮三种类型共25个橙酮衍生物，并通过熔点，1H NMR，13C NMR，ESI-MS和元素分析对目标化合物进行了结构表征，其中9个化合物 (2h～2m， 5a～5c)未见文献报道. 通过四甲基偶氮唑盐(MTT)法对目标化合物的抑制人宫颈癌细胞Hela活性进行了体外评价，结果表明：化合物2b，5b，2s和2g的半数抑制浓度IC50为44.3，31.1，43.8和41.9 μmol/L.
黄新炜 , 王征 , 陈巧利 , 孙艳妮 , 王翠玲 , 刘竹兰 , 刘建利 . 橙酮衍生物的合成及初步抗肿瘤活性研究[J]. 有机化学, 2013 , 33(12) : 2565 -2571 . DOI: 10.6023/cjoc201305032
Aurones are an important type of flavonoids with broad biological activities and pharmacological effects, such as anti-tumor, anti-inflammatory, antioxidant, antibacterial, insect antifeedant etc. They are less common and not widely distributed in nature. The low contents in nature lead to high cost of extraction and separation. In order to extend the compounds diversity and study structure activity relationship, phenoxyacetic acid, 2,3,5-trimethylphenol, 4-chlorol-3,5-dimethylphenol, chloroacetic acid and various aromatic aldehydes are used as starting materials to synthesize three types of aurone derivatives. Their structures were characterized by melting point, 1H NMR, 13C NMR, ESI-MS and elemental analysis. Nine of twenty five synthetic compounds 2h～2m, 5a～5c were unreported in the literature. All the target compounds were evaluated for antitumor activities against Hela human cervical carcinoma cell lines by methyl thiazolyl tetrazolium (MTT) method. The results showed that compounds 2b, 5b, 2s and 2g exhibited potentially high activity against Hela human cervical carcinoma cell lines with IC50 value of 44.3, 31.1, 43.8 and 41.9 μmol/L.
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