Synthesis and Antitumor Activities of Novel 1,2,3-Triazole-fused Oligoconjugates Based on Nucleoside and Saccharide

doi:10.6023/cjoc201205031

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (9): 1673-1677.DOI: 10.6023/cjoc201205031 Previous Articles Next Articles

Articles

新型核苷和单糖 1,2,3-三唑寡聚缀合物的合成及抗肿瘤活性

金培元^a, 卢金荣^a, 赵长琦^b, 巨勇^a,c

a 清华大学化学系生命有机磷化学及化学生物学教育部重点实验室北京 100084;
b 北京师范大学生命科学学院北京 100875;
c 兰州大学功能有机分子化学国家重点实验室兰州 730000

收稿日期:2012-05-25 修回日期:2012-07-02 发布日期:2012-06-21
通讯作者: 巨勇 E-mail:juyong@tsinghua.edu.cn
基金资助:
国家自然科学基金(No.21172130)和国家重点基础研究发展规划(973 计划) (No.2012CB821600)资助项目

Synthesis and Antitumor Activities of Novel 1,2,3-Triazole-fused Oligoconjugates Based on Nucleoside and Saccharide

Jin Peiyuan^a, Lu Jinrong^a, Zhao Changqi^b, Ju Yong^a,c

a Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084;
b School of Life Science, Beijing Normal University, Beijing 100875;
c State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 73000

Received:2012-05-25 Revised:2012-07-02 Published:2012-06-21
Supported by:
Project supported by the National Natural Science Foundation of China (No.21172130) and the National Program on Key Basic Research Project (973 Program) (No.2012CB821600)

1. Synthesis and Antitumor Activities of Novel 1,2,3-Triazole-fused Oligoconjugates Based on Nucleoside and Saccharide.PDF(353KB)

Abstract

Novel 1,2,3-triazole-fused oligoconjugates 7～12 based on nucleoside and saccharide were synthesized via click chemistry. The structures were confirmed by ¹H NMR and MS, and their antitumor activities were assayed against cervix cancer HeLa cells in vitro. The preliminary bioassay test shows that only bis(triazole) nucleoside 11a considerably inhibited the growth of cervix cancer HeLa cells and was much better than azidothymidine.

Key words: oligomerization, conjugates, click chemistry, antitumor activity

Cite this article

Jin Peiyuan, Lu Jinrong, Zhao Changqi, Ju Yong. Synthesis and Antitumor Activities of Novel 1,2,3-Triazole-fused Oligoconjugates Based on Nucleoside and Saccharide[J]. Chin. J. Org. Chem., 2012, 32(9): 1673-1677.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Huisgen, R.; Grashey, R. J. Sauer in Chemistry of Alkenes, Interscience, New York, 1964, pp. 806～877.

[2] Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.

[3] Droumaguet, C. L.; Wang, C.; Wang, Q. Chem. Soc. Rev. 2010, 39, 1233.

[4] Horne, W. S.; Yadav, M. K.; Stout, C. D.; Ghadiri, M. R. J. Am. Chem. Soc. 2004, 126, 15366.

[5] Kumar, A.; Pandey, P. S. Trahedron Lett. 2009, 50, 5842.

[6] Kumar, A.; Chhatra, R. K.; Pandey, P. S. Org. Lett. 2010, 12, 24.

[7] Vijayalakshmi, N.; Maitra, U. J. Org. Chem. 2006, 71, 768.

[8] Zhong, Z. Q.; Zhao, Y. Org. Lett. 2007, 9, 2891.

[9] Whitmarsh, S. D.; Redmond, A. P.; Sgarlata, V.; Davis, A. P. Chem. Commun. 2008, 44, 3669.

[10] Zhang, J. W.; Luo, J. T.; Zhu, X. X. Langmuir 2010, 26, 2958.

[11] Richeter, S.; Rebek, J. J. Am. Chem. Soc. 2004, 126, 16280.

[12] Parkin, G. Chem. Rev. 2004, 104, 699.

[13] Zhang, J. W.; Junk, M. J. N.; Luo, J. T.; Hinderberger, D.; Zhu, X. X. Langmuir 2010, 26, 13415.

[14] Hu, J.; Zhang, M.; Yu, L. B.; Ju, Y. Bioorg. Med. Chem. Lett. 2010, 20, 4342.

[15] Pore, V. S.; Aher, N. G.; Kumar, M. Tetrahedron 2006, 62, 11178.

[16] Vatmurge, N. S.; Hazra, B. G.; Pore, V. S. Org. Biomol. Chem. 2008, 6, 3823.

[17] Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117.

[18] Cheng, K. G.; Liu, J.; Sun, H. B.; Xie, J. Chem. Biodiversity 2010, 7, 690.

[19] Lee, L. V.; Mitchell, M. L.; Huang, S. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C. H. J. Am. Chem. Soc. 2003, 125, 9588.

[20] Binder, W. H.; Sachsenhofer, R. Macromol. Rapid Commun. 2007, 28, 15.

[21] Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Bar-bachyn, M. R. J. Med. Chem. 2000, 43, 953.

[22] Sherement, E. A.; Tomanov, R. I.; Trukhin, E. V.; Berestovitskaya, V. M. Russ. J. Org. Chem. 2004, 40, 594.

[23] Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V. Macromolecules 2005, 38, 3663.

[24] San-Felix, A.; Alvarez, R.; Velazquez, S.; De Clerq, E.; Balzarini, J.; Camarasa, M. J. Nucleosides Nucleotides 1995, 14, 595.

[25] Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.

[26] Huisgen, R.; Szeimies, G.; Mobius, L. Chem. Ber. 1967, 100, 2494.

[27] Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.

[28] Jin, X. Y.; Yang, R. C.; Jin, P. Y.; Xiao, Q.; Ju, Y. Synthesis 2007, 2967.

[29] Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.

[30] Qi, X. J.; Liu, S. X.; Liu, T.; Dang, L.; Yang, X.; Yu, W. N.; Wang, H. M. Acta Chim. Sinica 2011, 69, 1803.

[31] Kong, L. Z; Qiao, H. M; Jiang, B. B. Acta Chim. Sinica 2011, 69, 1817.

[32] Zhang, S. H.; Zhu, H. W.; Zhang, M. Z.; Ni, P. H. Acta Chim. Sinica 2011, 69, 2166

[33] Zhang, Z.; Ju, Y.; Zhao, Y. F. Chem. Lett. 2007, 36, 1450.

[34] Jin, P. Y.; Jin, P.; Ruan, Y. A.; Ju, Y.; Zhao, Y. F. Synlett 2007, 3003.

[35] Hu, J.; Yu, L. B.; Zhang, M.; Ju, Y. Chin. J. Chem. 2011, 29, 1139.

[36] Olivero, O. A.; Tejera1, A. M.; Fernandez, J. J.; Taylor, B. J.; Das, S.; Divi, R. L.; Poirier, M. C. Mutagenesis 2005, 20, 146.

[37] Wu, D. M.; Ji, S. H.; Wu, Y.; Ju, Y.; Zhao, Y. F. Bioorg. Med. Chem. Lett. 2007, 17, 2983.

[38] Trofimov, B. A.; Parshina, L. N.; Lavrov, V. I.; Sobenina, L. N.; Mikhaleva, A. I.; Shevchenko, S. G.; Kovostova, S. E.; Vins, V. V.; Feldman, V. D. Zh. Prikl. Khim. 1992, 65, 401.

[39] Mourer, M.; Hapiot, F.; Tilloy, S.; Monflier, E.; Menuel, S. Eur. J. Org. Chem. 2008, 34, 5723.

[40] Sato, E.; Yokozawa, T.; Endo, T. Macromolecules 1993, 26, 5187.Cherbuliez, E.; Gowhari, M.; Rabinowitz, J. Helv. Chim. Acta 1964, 47, 2098.

新型核苷和单糖 1,2,3-三唑寡聚缀合物的合成及抗肿瘤活性

Synthesis and Antitumor Activities of Novel 1,2,3-Triazole-fused Oligoconjugates Based on Nucleoside and Saccharide

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[2]	Panxing Pang, Rong Ning, Chuang Zhu, Wenjie Huang, Xianli Ma, Caina Jiang, Fangyao Li, Xiaoqun Zhou. Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2126-2135.
[3]	Kanghui Duan, Junlong Tang, Wanqing Wu. Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 826-854.
[4]	Hao Zhang, Qingbin Zhao, Zhongrui Ruan, Zhenxing Liu. Recent Development of SuFEx Reaction between Silyl Ethers and Sulfur(VI) Fluoride Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3569-3579.
[5]	Weiqin Liu, Lihui Shao, Chengpeng Li, Yayu Zou, Haitao Long, Yan Li, Qiangsheng Ge, Zhenchao Wang, Guiping Ouyang. Synthesis and Antitumor Activity of 3-Hydrazone Quinazolinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 214-222.
[6]	Dongyan Hu, Guangtian Han, Xi'an Li, Huazhong Ren, Lirong Yue, Li Guo, Jiafu Feng. Synthesis and Evaluation in vitro of Novel Harmine Derivatives as Anticancer Activity Agents [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1863-1871.
[7]	Lu Xue, Lihua Zhang, Chengyu Zhang, Xin Zhao, Weifan Dang, Zhaoxin Wang, Chunhua Wang, Tongchuan Suo, Xiaohui Yan. Discovery of Tiancimycin Congeners from Streptomyces sp. CB03234-S [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1241-1247.
[8]	Qiang Huang, Tingting Deng, Jiayun Zhu, Jun Li, Feifei Li. Study on the Green Synthesis of β-Hydroxy-1,2,3-triazoles Catalyzed by An Amino-Functionalized Graphene-Supported Ag-Cu Composites [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 534-542.
[9]	Honglin Dai, Xiaojie Si, Lingling Chi, Hao Wang, Chao Gao, Zhengjie Wang, Limin Liu, Jiajie Ma, Fuqiang Yu, Hongmin Liu, Yu Ke, Qiurong Zhang. Synthesis and Antitumor Activity Evaluation of 2,4,6-Trisubstituted Quinazoline Derivatives Containing Thiazole Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3853-3862.
[10]	Zhengjie Wang, Honglin Dai, Xiaojie Si, Chao Gao, Limin Liu, Luye Zhang, Yang Zhang, Yadan Song, Peirong Zhao, Jiaxin Zheng, Yu Ke, Hongmin Liu, Qiurong Zhang. Synthesis and Antitumor Activity of 2,4,6-Trisubstituted Novel Quinazoline Derivatives Containing Trifluoromethyl [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 249-256.
[11]	Lijun Yin, Chaoqun Li, Xiaoxia Wu, Guangsen Xu, Zhiying Li, Yuemao Shen. Synthesis of (E)-N-(4-Styrene) Acrylamides for DNA Topoisomerase IIα Inhibitors and Antitumor Agents [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 293-301.
[12]	Jiaoli Ma, Penghu Guo, Jing Li, Xincheng Liao, Huicheng Cheng. Synthesis and Antitumor Activity of Amide Derivatives Containing 1,3,4-Thiadiazole and Pyrazole Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3214-3222.
[13]	Ningbo Li, Li Xu, Rong Ma, Qi Fan, Bo Li, Jie Qiao, Rui Guo, Xinhua Xu. Synthesis and Antitumor Activities of Novel Organic Sulfur (Selenium) Tegafur Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2723-2734.
[14]	Liang Shao, Fan Yang, Weijia Li, Fei Yu. Design, Synthesis and Anti-influenza A Virus Evaluation of Oleanolic Acid C3-Glycoconjugates [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2454-2466.
[15]	Yinghao Liu, Fangxia Lin, Yinfeng Tan, Jingyu Yang, Bin Zhang, Xueming Zhou, Xinming Song. Three New Phenanthraquinones from the Root of Dendrobium nobile [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2112-2115.