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有机化学
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有机化学 ›› 2014, Vol. 34 ›› Issue (10): 2130-2134.DOI: 10.6023/cjoc201404021 上一篇    下一篇

研究简报

新型4-芳基-5,6,7,8-四氢喹唑啉-2-胺类化合物的合成及其生物活性研究

鲍名凯a, 熊丝丝b, 曹明珍a, 徐徐a, 王石发a, 张志杰b   

  1. a. 南京林业大学化学工程学院 南京 210037;
    b. 中国中医科学院中药研究所 北京 100700
  • 收稿日期:2014-04-12 修回日期:2014-05-07 发布日期:2014-06-11
  • 通讯作者: 王石发, 张志杰 E-mail:wsfyyq@njfu.com.cn
  • 基金资助:

    国家林业公益性行业科研专项（No.201104015）和国家自然科学基金（No.31170538）资助项目.

Synthesis and Biological Activities of Novel 4-Aryl-5,6,7,8-tetrahydroquinazolin-2-amine Derivatives

Bao Mingkaia, Xiong Sisib, Cao Mingzhena, Xu Xua, Wang Shifaa, Zhang Zhijieb   

  1. a. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b. Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700
  • Received:2014-04-12 Revised:2014-05-07 Published:2014-06-11
  • Supported by:

    Project supported by Forestry Public Sector Research Found of State Forestry Administration of China (No. 201104015) and the National Natural Science Foundation of China (No. 31170538).

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以α-蒎烯为原料，经加成-氧化后与多种芳香醛缩合制得中间体4-芳亚甲基异松蒎酮3a～3h，3a～3h与盐酸胍在叔丁醇钾催化作用下合成8种新型4-芳取代-5，6，7，8，-四氢喹唑啉-2-胺类化合物4a～4h. 其结构经IR，1H NMR，13C NMR，GC-MS和元素分析表征. 初步探讨了所合成化合物对人乳腺癌细胞MCF-7和人肺癌细胞A549的体外生物活性，结果显示部分化合物具有很好的抗肿瘤活性.

关键词: α-蒎烯, 四氢喹唑啉-2-胺, 合成, 抗肿瘤活性

The intermediate compounds 4-arylidene isopinanones 3a～3h were synthesized by using α-pinene as starting material in three steps reaction including addition, oxidation, and condensation with aromatic aldehydes. Subsequently, eight new 4-aryl-5,6,7,8-tetrahydroquinazolin-2-amine derivatives 4a～4h were obtained by reacting 3a～3h with guanidine hydrochloride under t-BuOK. Their structures were characterized by IR, 1H NMR, 13C NMR, GC-MS and elemental analysis. Biological activities of 4a～4h against MCF-7 (human breast cancer) and A549 (human lung cancer) were tested and the results showed that some of compounds exhibited good antitumor activity.

Key words: α-pinene, tetrahydroquinazolin-2-amine, synthesis, antitumor activity