Studies on Synthesis and Bioactivity of N8-Deaza-N5-tetrahydrofolate Analogues

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (11): 1721-1725. Previous Articles Next Articles

Full Papers

N⁸-去氮-N⁵-取代四氢叶酸类似物的设计合成及生物活性研究

闫汝锋，田超，郭莹，张志丽，王孝伟，刘俊义*

(北京大学药学院化学生物学系北京100191)

收稿日期:2010-03-06 修回日期:2010-06-10 发布日期:2010-06-24
通讯作者: 闫汝锋 E-mail:yanrf031@163.com

Studies on Synthesis and Bioactivity of N⁸-Deaza-N⁵-tetrahydrofolate Analogues

YAN Ru-Feng, TIAN Chao, GUO Ying, ZHANG Zhi-Li, WANG Xiao-Wei, LIU Jun-Yi

(Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191)

Received:2010-03-06 Revised:2010-06-10 Published:2010-06-24

Abstract

The backbone of folate analogue was obtained by linking di-ethyl-N-(p-aminobenzoyl)-L- glutamate and 2-amino-4-hydroxy-6-(hydroxymethyl)pyrido[3,2-d]pyrimidine. Three new 8-deazatetra- hydrofolate analogues were synthesized after reducing the pyrimidine and linking different substituents on N⁵position. The compounds were characterized by ¹H NMR and MS techniques. The inhibitory activities of the compounds against human dihydrofolate reductase were determined. The re-sults showed that the bioactivities of the compounds were related with different substituents on N⁵position.

Key words: N⁸-deaza-N⁵-substitutedtetrahydrofolate analogue, dihydrofolate reductase, anticancer activity

Cite this article

YAN Ru-Feng, TIAN Chao, GUO Ying, ZHANG Zhi-Li, WANG Xiao-Wei, LIU Jun-Yi. Studies on Synthesis and Bioactivity of N⁸-Deaza-N⁵-tetrahydrofolate Analogues[J]. Chin. J. Org. Chem., 2010, 30(11): 1721-1725.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Weishu Zhang, Lifei Nie, Khurshed Bozorov, Haji Akber Aisa, Jiangyu Zhao. Synthesis of Diethyl 2,5-Diaminothiophene-3,4-dicarboxylate Derivatives and Antitumor Activity Study [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2543-2552.
[2]	Jing Zhao, Zhe Jin, Run Wang, Xin'geng Zhang, Yingmei Han, Chun Hu, Xiaoping Liu, Chuanming Zhang, Liping Jin. Design, Synthesis and Anticancer Activity of 2-((Pyridin- 2-ylmethyl)thio)-1H-benzimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2172-2183.
[3]	Yan Zeng, Lifei Nie, Chao Niu, Aytilla Mamatjan, Khurshed Bozorov, Jiangyu Zhao, Haji Akber Aisa. Synthesis and Biological Activities of Dihydrooxazolo[5,4-d]-pyrrolo[1,2-a]pyrimidinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 543-556.
[4]	Shenghui Wang, Yongfeng Guan, Xiujuan Liu, Xinying Yuan, Guangxi Yu, Yinru Li, Yanbing Zhang, Jian Song, Wen Li, Saiyang Zhang. Design, Synthesis and Anticancer Activity Studies of Novel Quinoline-Indole Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3617-3624.
[5]	Xin Liu, Runmei Xu, Lin Wang, Yaxue Liu, Zhihao Chen, Wei Qin, Yushun Tian. Synthesis and Evaluation in vitro of Dihydrothiophenopyridine-Chalcone Derivatives as Anticancer Activity Agents [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3550-3559.
[6]	Jing Cong, Fang Fang, Liangmin Xue, Meng Wang, Chao Tian, Xiaowei Wang, Junyi Liu, Zhili Zhang. Synthesis and Antitumor Activity of Novel Pyrimidine Monocyclic Nonclassical Antifolates [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 776-787.
[7]	Maihesuti Liwaliding, Yu Junjie, Wang Qi, Cao Jianguo, Huang Guozheng. Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2764-2771.
[8]	Mao Zewei, Liu Bei, Zhu Ping, Zhang Lijun, Zhu Jiahong, Wu Linze, Wan Chunping. Synthesis and Biological Evaluation of Piperazine Substituted 3-Aryl-5-furanyldihydropyrazole Amide Derivatives [J]. Chin. J. Org. Chem., 2018, 38(8): 2167-2173.
[9]	Huang Xinwei, Liu Jianli. Synthesis and Anticancer Activities of Novel Pyranocoumarin Fused Pyrimidine Based on Cyanoenamine [J]. Chin. J. Org. Chem., 2018, 38(5): 1233-1241.
[10]	Zhang Lei, Liu Lai, Zheng Chengyue, Wang Yang, Wang Jing, Yao Qizheng. Synthesis of Novel Indirubin Derivatives and Their Effects on the Proliferation, Cell Cycle and Apoptosis in Acute Myeloblastic Leukemia HL-60 Cells [J]. Chin. J. Org. Chem., 2017, 37(6): 1523-1529.
[11]	Liu Juanjuan, Lu Yanju, Wang Jing, Bi Liangwu, Zhao Zhendong. Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid [J]. Chin. J. Org. Chem., 2017, 37(3): 731-738.
[12]	Imerhasan Mukhtar, Helil Setiwaldi, Mahmud Muhammed Amin. Synthesis and in vitro Anticancer Activity of N-Methylisoxazolinium-Salts with Carboxyl or Ester Groups against Cell Division Cycle 25B Phosphatase and Protein Tyrosine Phosphatase-1 [J]. Chin. J. Org. Chem., 2017, 37(2): 496-502.
[13]	Li Zemin, Huang Daorui, Ma Congming, Xu Xiaojuan, Liu Zuliang, Yao Qizheng. Convenient Aminative Ring-Opening Reaction of 7-Amino-6-nitro-[1,2,5]oxadiazolo[3,4-b]pyridine-1-oxide and Antitumor Activity of Corresponding Products [J]. Chin. J. Org. Chem., 2016, 36(9): 2236-2241.
[14]	Liu Ming, Liu Yang, Liu Ailin, Zhang Dongkai, Chen Minggui, Wu Changchun, Hua Xuewen, Zhou Sha, Li Zhengming. Synthesis and Bioactivities of Novel Coumarin Derivatives Containing Sulfinic Esters or Sulfinamide Moiety [J]. Chin. J. Org. Chem., 2016, 36(7): 1653-1661.
[15]	Chen Yanhua, Hou Xiyan, Zhi Defu, Li Chang, Tian Tian, Sun Jingyang, Zhao Longxuan, Zhao Chunhui. Synthesis, Characterization and Anticancer Activity of Oleanolic Acid and Ursolic Acid Derivatives [J]. Chin. J. Org. Chem., 2016, 36(4): 795-802.

N⁸-去氮-N⁵-取代四氢叶酸类似物的设计合成及生物活性研究

Studies on Synthesis and Bioactivity of N⁸-Deaza-N⁵-tetrahydrofolate Analogues

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

N8-去氮-N5-取代四氢叶酸类似物的设计合成及生物活性研究