Synthesis and Cytotoxic Activity of New 3-Aryl-5-furanyl-4, 5-dihydroisoxazoline Derivatives

doi:10.6023/cjoc201711005

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 949-954.DOI: 10.6023/cjoc201711005 Previous Articles Next Articles

Notes

新型3-芳基-5-呋喃基-4,5-二氢异噁唑啉衍生物的合成及其细胞毒活性

黎勇坤^a, 刘蓓^a, 张丽君^a, 朱加洪^a, 万春平^b, 毛泽伟^a

a 云南中医学院中药学院昆明 650500;
b 云南中医学院第一附属医院中心实验室昆明 650021

收稿日期:2017-11-02 修回日期:2017-12-04 发布日期:2017-12-15
通讯作者: 万春平, 毛泽伟 E-mail:wanchunping1012@163.com;maozw@ynutcm.edu.cn
基金资助:
国家自然科学基金（No.81460624）和云南省科学技术厅-云南中医学院应用基础研究联合专项（No.2017FF117（-023））资助项目.

Synthesis and Cytotoxic Activity of New 3-Aryl-5-furanyl-4, 5-dihydroisoxazoline Derivatives

Li Yongkun^a, Liu Bei^a, Zhang Lijun^a, Zhu Jiahong^a, Wan Chunping^b, Mao Zewei^a

a College of Pharmaceutical Science, Yunnan University of Traditional Chinese Medicine, Kunming 650500;
b Central Laboratory, The No.1 Affiliated Hospital of Yunnan University of Traditional Chinese Medicine, Kunming 650021

Received:2017-11-02 Revised:2017-12-04 Published:2017-12-15
Contact: 10.6023/cjoc201711005 E-mail:wanchunping1012@163.com;maozw@ynutcm.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 81460624) and the Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Traditional Chinese Medicine (No. 2017FF117 (-023))

1. Synthesis and Cytotoxic Activity of New 3-Aryl-5-furanyl-4, 5-dihydroisoxazoline Derivatives.PDF(2459KB)

Abstract

Dihydroisoxazoline is a heterocyclic compound with a variety of biological properties. In this study, ten new 3-(4-piperazinyl)phenyl-5-(2-furyl)-4,5-dihydroisoxazoline derivatives (3~12) have been prepared by the general principle of molecular hybridization based on former work. The structures were characterized by IR, ¹H NMR, ¹³C NMR and HRMS. In vitro cytotoxic activity against a panel of human tumor cell lines (Hela, A549 and SGC7901) was evaluated by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. The result indicated that dihydroisoxazoline derivatives showed potential cytotoxic activity, and the substituents of the NH group of piperazine ring had an obvious influence on cytotoxic activities. Especially, compound 4, 6 and 11 were found to be better inhibition against human tumor cell lines, which were found to be similar cytotoxic activity to positive control 5-fluorouracil. Further FACs analysis showed that compounds 4 and 11 significantly induced death in A549 cell.

Key words: dihydroisoxazoline, synthesis, cytotoxic activity, FACs analysis

Cite this article

Li Yongkun, Liu Bei, Zhang Lijun, Zhu Jiahong, Wan Chunping, Mao Zewei. Synthesis and Cytotoxic Activity of New 3-Aryl-5-furanyl-4, 5-dihydroisoxazoline Derivatives[J]. Chin. J. Org. Chem., 2018, 38(4): 949-954.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Bianchi, G.; Micheli, C. D.; Gandolfi, R. J. Chem. Soc., Perkin Trans. 1972, 1, 1711.
[2] Byrappa, S.; Raj, M. H.; Kungyal, T.; Kudva N, N. U.; Salimath, B. P.; Rai, K. M. L. Eur. J. Med. Chem. 2017, 126, 218.
[3] Zghab, I.; Trimeche, B.; Mansour, M. B.; Hassine, M.; Touboul, D.; Jannet, H. B. Arabian J. Chem. 2017, 10, S2651.
[4] Yu, W. D.; Nie, Y. M.; Yuan, H.; Yan, J.; Yi, H. B. Inorg. Chem. Commun. 2017, 84, 134.
[5] Liu, X. D.; Ma, H. Y.; Xing, C. H.; Lu, L. Chin. Chem. Lett. 2017, 28, 1780.
[6] Rawat, P.; Singh, R. N.; Baboo, V.; Niranjan, P.; Rani, H.; Saxena, R.; Ahmad, S. J.Mol. Struct. 2017, 1129, 37.
[7] Hamadi, N. B.; Msaddek, M. Arabian J. Chem. 2017, 10, S800.
[8] Puttaswamy, N.; Kumar, G. S. P.; Al-Ghorbani, M.; Vigneshwaran, V.; Prabhakar, B. T.; Khanum, S. A. Eur. J. Med. Chem. 2016, 114, 153.
[9] Curtis, M. P.; Vaillancourt, V.; Goodwin, R. M.; Chubb, N. A. L.; Howson, W.; McTier, T. L.; Pullins, A.; Zinser, E. W.; Meeus, P. F. M.; Woods, D. J.; Hedges, L.; Stuk, T.; Price, J. E.; Koch, J. D.; Menon, S. R. Bioorg. Med. Chem. Lett. 2016, 26, 1831.
[10] Khazir, J.; Singh, P. P.; Reddy, D. M.; Hyder, I.; Shafi, S.; Sawant, S. D.; Chashoo, G.; Mahajan, A.; Alam, M. S.; Saxena, A. K.; Arvinda, S.; Gupta, B. D.; Kumar, H. M. S. Eur. J. Med. Chem. 2013, 63, 279.
[11] Amin, K. M.; Kamel, M. M.; Anwar, M. M.; Khedrc, M.; Syam, Y. M. Eur. J. Med. Chem. 2010, 45, 2117.
[12] Thabit, M. G.; El Bialy, S. A. A.; Nasr, M. N. A. Heterocycl. Commun. 2015, 21, 23.
[13] Ma, Y. L.; Zheng, X.; Gao, H.; Wan, C. P.; Rao, G. X.; Mao, Z. W. Molecules 2016, 21, 1684.
[14] Lin, Y. P.; Hu, C. Y.; Zheng, X.; Wang, X. L.; Wan, C. P.; Mao, Z. W. Chin. J. Org. Chem. 2017, 37, 237(in Chinese). (林玉萍, 虎春艳, 郑喜, 王秀丽, 万春平, 毛泽伟, 有机化学, 2017, 37, 237.)
[15] Gao, H.; Zheng, X.; Wang, S.; Yang, L. L.; Mao, Z. W. Chemistry 2017, 80, 976(in Chinese). (高慧, 郑喜, 王斯, 杨林丽, 毛泽伟, 化学通报, 2017, 80, 976.)
[16] Zhang, L.; Li, W. Y.; Liu, L.; Zheng, C. Y.; Wang, Y.; Xu, Y. S.; Shi, D. B.; Nie, X. Q.; Guo, J. Y.; Zhu, C. Y.; Wang, J. Chin. J. Org. Chem. 2017, 37, 1721(in Chinese). (张磊, 李文赟, 刘来, 郑诚月, 王杨, 徐应淑, 史大斌, 聂绪强, 国佳莹, 朱春媛, 王京, 有机化学, 2017, 37, 1721.)

新型3-芳基-5-呋喃基-4,5-二氢异噁唑啉衍生物的合成及其细胞毒活性

Synthesis and Cytotoxic Activity of New 3-Aryl-5-furanyl-4, 5-dihydroisoxazoline Derivatives

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[6]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[7]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[8]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[9]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[10]	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.
[11]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.