Synthesis and the biological activity of chiral 3,  5-disubstituted S- triazolo[3, 4-b]-2, 4-dihydrogen-1, 3,  5-thiadiazines

Abstract

Six Novel compounds were synthesized by the reaction of 3-aryl-5- mercapto-1, 2, 4-S-triazoles with formaldehyde and S-(-)-α- phenylethylamine in the presence of as acid catalyst. The reaction conditions were investigated. The structure of these compounds were established by elemental analysis, IR, ^1H NMR, MS and specificrotation. Some these compounds show that some compounds possess strong antibacterial activities.

Key words: ARYL GROUP, MERCAPTO GROUP, PYRRODIAZOLE P, STRUCTURAL ANALYSIS, THIADIAZINE P, BIOLOGICAL ACTIVITY, MANNICH REACTION, CHIRALITY

CLC Number:

O621

Cite this article

Shi Haoxin;Wang Zhongyi;Shi Haijian. Synthesis and the biological activity of chiral 3, 5-disubstituted S- triazolo[3, 4-b]-2, 4-dihydrogen-1, 3, 5-thiadiazines[J]. Chin. J. Org. Chem., 2000, 20(3): 344-347.

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]	Yang Liu, Xiang Huang, Min Wang, Jian Liao. Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1499-1509.
[4]	Qian Wang, Yuqi Liu, Zongquan Wu. Synthesis and Structure Control of Chiral Helical Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4141-4146.
[5]	Jiayi Zhao, Yicong Ge, Chuan He. Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3352-3366.
[6]	Hui Li, Liang Yin. Research Progress of Copper-Catalyzed Direct Vinylogous Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1573-1585.
[7]	Tongli Zhang, Jun Yan, Jingli He, Xuezhen Kou, Jiefeng Shen, Delong Liu, Wanbin Zhang. Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1747-1758.
[8]	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.
[9]	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.
[10]	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.
[11]	Jieming Zhang, Hang Ni, Qi Wu, Junfeng Yang, Junliang Zhang. Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3118-3128.
[12]	Sha Zhou, Mukuo Wang, Weibin Xie, Shaa Zhou, Lixia Xiong, Yu Zhao, Zhengming Li. Synthesis and Insecticidal Activities of Novel Optically Active Dicarboxamides Containing N-Trifluoroacetyl Sulfulimiyl Substituents [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3532-3538.
[13]	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.
[14]	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.
[15]	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.

手性-3, 5-二取代-1', 2', 4'-三唑-[3', 4'-b]-2, 4-二氢间噻二嗪的合成及生物活性