Synthesis and Biological Activities of 4-Alkyl-6-aryl-1,3-thiazines

doi:10.6023/cjoc201212026

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1478-1482.DOI: 10.6023/cjoc201212026 Previous Articles Next Articles

Articles

4-烷基-6-芳基-1,3-噻嗪的合成与生物活性

李婉^a, 胡艾希^a, 刘艾林^b, 彭俊梅^a, 夏林^a, 谭卫清^a

a 湖南大学化学化工学院长沙 410082;
b 中国医学科学院药物研究所北京 010

收稿日期:2012-12-17 修回日期:2013-03-02 发布日期:2013-03-06
通讯作者: 胡艾希, 刘艾林 E-mail:axhu@hnu.edu.cn;liuailin@imm.ac.cn
基金资助:
国家教育部博士点专项基金(No. 20040532002)资助项目.

Synthesis and Biological Activities of 4-Alkyl-6-aryl-1,3-thiazines

Li Wan^a, Hu Aixi^a, Liu Ailin^b, Peng Junmei^a, Xia Lin^a, Tan Weiqing^a

a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
b Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050

Received:2012-12-17 Revised:2013-03-02 Published:2013-03-06
Supported by:
Project supported by the Ph.D. Programs Foundation of Ministry of Education of China (No. 20040532002).

A series of 1,3-thiazine derivatives 1a～1p were designed and synthesized by the reaction of aromatic aldehyde via condensation and cyclization, and their inhibitory activity of nueraminidase (NA) and serotonin reuptake (SERT) were evaluated in vitro. The pharmacological results showed that compound 1i exhibits good activity of NA with the inhibitory rate of 68.91% at the concentration of 40 μg/mL, which is similar to oseltamivir (inhibitory rate is 72.6%), moreover, at the concentration of 10.0 μg/mL, compounds 1d, 1e and 1f exhibit good serotonin reuptake inhibitory activity with inhibitory rates of 99.5%, 99.6% and 99.8%, respectively.

Key words: synthesis, 1,3-thiazine, neuraminidase inhibitors, serotonin transportor inhibitors

Cite this article

Li Wan, Hu Aixi, Liu Ailin, Peng Junmei, Xia Lin, Tan Weiqing. Synthesis and Biological Activities of 4-Alkyl-6-aryl-1,3-thiazines[J]. Chin. J. Org. Chem., 2013, 33(07): 1478-1482.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Sun, C. W.; Zhang, X. D.; Huang, H.; Zhou, P. Bioorg. Med. Chem. 2006, 14, 8574.
[2] Baz, M.; Abed, Y.; Boivin, G. Antiviral Res. 2007, 74, 159.
[3] Baranovich, T.; Webster, R. G.; Govorkova, E. A. Curr. Opin. Virol. 2011, 1, 574.
[4] Collins, P. J.; Haire, L. F.; Lin, Y. P. Nature 2008, 453, 1258.
[5] Abed, Y.; Nehm, B.; Baz, M.; Boivin, G. Antiviral Res. 2008, 77, 163.
[6] Mitrasinovic, P. M. Curr. Drug. Targets 2010, 11, 315.
[7] Chand, P.; Kotian, P. L.; Morris, P. E.; Bantia, S.; Walshb, D. A.; Babu, Y. S. Bioorg. Med. Chem. 2005, 13, 2665.
[8] You, Q. D. Pharmaceutical Chemistry, Chemical Industry Press, Beijing, 2004, pp. 145～149 (in Chinese). (尤启东, 药物化学, 化学工业出版社, 北京, 2004, pp. 145～149.)
[9] Christmas, D. M.; Potokar, J. P.; Davies, S. J. C. Neurobiol. Dis. Treat. 2011, 7, 431
[10] Akhondzadeh, S.; Jafari, S.; Raisi, F.; Nasehi, A. A.; Ghoreishi, A.; Salehi, B.; Mohebbi-Rasa, S.; Raznahan, M. Depression Anxiety 2009, 26, 607.
[11] Francesc. A. ACS Chem. Neurosci. 2013, 4, 5.
[12] Lynette. C. D.; Wouter. K.; Nathan. C. M. ACS Chem. Neurosci. 2013, 4, 16.
[13] Hector, H.; Sylvain, B.; Leticia, Q.; Estibaliz, S.; Aurelio, O. Tetrahedron Lett. 2006, 47, 1153.
[14] Temple, C.; Wheeler, G. P.; Comber, R. N.; Elliot, R. D.; Montgomery, J. A. J. Med. Chem. 1983, 26, 1614.
[15] Singh, U. P.; Pathak, M.; Dubey, V.; Bhat, H. R.; Gahtori, P.; Singh, R. K. Chem. Biol. Drug Des. 2012, 80, 572.
[16] Koketsu, M.; Tanaka, K.; Takenaka, Y.; Kwong, C. D.; Ishihara, H. Eur. J. Pharm. Sci. 2002, 15, 307.
[17] Gazic, I.; Bosak, A.; Sinko, G.; Vinkovic, V.; Kovarik, Z. Anal. Bioanal. Chem. 2006, 385, 1513.
[18] Handley, D. A.; McCullough, J. R.; Crowther, S. D.; Morley, J. Chirality 1998, 10, 262.
[19] Landon, M. R.; Amaro, R. E.; Baron, R. Chem. Biol. Drug Des. 2008, 71, 106.
[20] Grienke, U.; Schmidtke, M.; Kirchmair, J. J. Med. Chem. 2010, 53, 778.
[21] An, J. H.; Lee, D. C. W.; Law, A. H. J. Med. Chem. 2009, 52, 2667.
[22] Wang, Y.; Hu, A. X.; Cao, G.; Li, G. X.; Zhang, J. Y.; Xia, L.; Ou, X. M.; Xu, J. B. Chin. J. Org. Chem. 2008, 28, 443 (in Chinese). (王宇, 胡艾希, 曹高, 李国希, 张建宇, 夏林, 欧晓明, 徐建兵, 有机化学, 2008, 28, 443.)

4-烷基-6-芳基-1,3-噻嗪的合成与生物活性

Synthesis and Biological Activities of 4-Alkyl-6-aryl-1,3-thiazines

PDF

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]	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.
[6]	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.
[7]	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.
[8]	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.
[9]	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.
[10]	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.
[11]	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.
[12]	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.
[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]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.