Synthesis and Biological Activity of N-Alkyl/aryl-N'-(4-arylthiazol-2-yl)- N''-glycosyl Guanidines

Abstract

The reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (1) and 2-amino-4- arylthiazoles (2a～2b) gave glucosylthioureas 3a～3b, which then reacted with alkyl/aryl amine in the presence of HgCl₂ to afford a series of new N-alkyl/aryl-N'-(4-arylthiazol-2-yl)-N''-glucosyl guanidines (4a～4e and 5a～5e). The structures of the new compounds were established on the basis of IR, ¹H NMR and MS spectra and all compounds took β-configuration. The anti-HIV and antibacterial activities of these compounds have been evaluated. Compounds 4b and 5d showed anti-HIV activity.

Key words: glucosylthiourea, glucosyl isothiocyanate, guanidinoglucoside, biological activity

Cite this article

SHI He-Fang,CAO Ling-Hua*^,1,2. Synthesis and Biological Activity of N-Alkyl/aryl-N'-(4-arylthiazol-2-yl)- N''-glycosyl Guanidines[J]. Chin. J. Org. Chem., 2005, 25(9): 1066-1070.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Mingjia Guang, Shuo Jiang, Baoyu Zhu, Rusong Zhang, Kunpeng Wang, Minghui Wang, Liangzhong Xu. Design, Synthesis and Insecticidal, Acaricidal Activities of Novel Pyrrole-2-carboxylic Acid and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2895-2904.
[2]	Qifan Wang, Yuanquan Zhang, Li Xing, Yuanxiang Zhou, Chenyu Gong, Bangcan He, Nian Zhang, Yongjun Wu, Wei Xue. Design, Synthesis and Biological Activity of Myricetin Derivatives Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1525-1536.
[3]	Can Yong, Yun Li, Tao Bi, Guofeng Chen, Dongxia Zheng, Zhouyu Wang, Yuanyuan Zhang. Research Progress on the Synthesis and Activity of D-Galactose Derived Small Galectin Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1307-1325.
[4]	Jie Luo, Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam Clifednamide K [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1224-1228.
[5]	Yajun Mao, Xiangmin Shao, Yangjie Li, Ruimei Cao, Yali Feng, Guangyu Zhai. Research Progress on the Synthesis of Quercetin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3588-3605.
[6]	Hongliang Xu, Jing Su, Zishi Wang, Chenxin Hou, Pengchong Wu, Yue Xing, Xiangshuai Li, Xiaolei Zhu, Yuncai Lu, Lijian Xu. Synthesis, Design and Three-Dimensional Quantitative Structure Activity Relationship (3D-QSAR) Research of Phenylpyrrole Fungicides [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3560-3570.
[7]	Xiaotian Qin, Junchao Zhang, Yuqing He, Rui Zhang, Hua Cheng, Cheng Chen, Xin Qin. Synthesis and Biological Activities of Coenzyme Q Derivatives Containing (4-Aryloxylaryl)amino Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2045-2054.
[8]	Meng Xu, Shenyuan Gao, Yuanxu Zeng, Anhui Gao, Lixin Gao, Lei Xu, Yubo Zhou, Jianrong Gao, Qing Ye, Jia Li. Synthesis and Evaluation of 3-(Indol-3-yl)-4-(pyrazolo[3,4- c]pyridazin-3-yl)maleimides as Potent Mutant Isocitrate Dehydrogenase-1 Inhibitors [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1991-2000.
[9]	Ting Jiang, Hong Pu, Yanwen Duan, Xiaohui Yan, Yong Huang. New Natural Products of Streptomyces Sourced from Deep-Sea, Desert, Volcanic, and Polar Regions from 2009 to 2020 [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1804-1820.
[10]	Jun He, Xuemei Tang, Qing Zhou, Feng Peng, Tingting Liu, Liwei Liu, Ming He, Chengwei Xie, Wei Xue. Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 708-718.
[11]	Zhenguo Zhang, Xiaoxiao Liu, Xinlong Zong, Yalin Yuan, Shuanglei Liu, Ting Zhang, Zishang Wu, Jingying Yang, Zhenhua Jia. Recent Advance on the Synthesis of 3,3'-Bisindolylmethane Derivatives under Transition-Metal-Free Catalytic Conditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 52-64.
[12]	Liang Wei, Tan Chengxia, Weng Jianquan, Liu Xinghai. Advances on Synthesis and Biological Activities of Mesoionic Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2702-2713.
[13]	Li Qianqian, Wu Zhongmei, Zhang Min, Zhang Yiping, Zhou Yingkai, Deng Hongmei, Song Liping. Synthesis and Preliminary Exploration of Biological Activity of 3-Aryl-4-arylamine Methyl Isoxazoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2108-2113.
[14]	Yu Youpei, Duan Wengui, Lin Guishan, Kang Guoqiang, Wang Xiaoyu, Lei Fuhou. Synthesis, Biological Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of Novel 4-Methyl-1,2,4-triazole-thioethers Containing gem-Dimethylcyclopropane Ring [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1647-1657.
[15]	Zhang Junhui, Zhu Yabo, Weng Jianquan, Yu Qian, Yuan Jing, Chen Jie. Synthesis and Biological Activity of Natural Stilbene-Inspired Substituted Styrylthiazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 1055-1061.

N-烷基/芳基-N'-(4-芳基噻唑-2-基)-N"-糖基胍的合成及生物活性研究