Home

Citation: ZHANG Chenglu, GUO Yang, WU Yifei, ZHU Chang'an, QU Ruifeng, SUN Lijie, WENG Xue, CHAI Jinhua. Synthesis and Biological Activities of 3-Aliphatic-1,2,4-Triazole[3,4-b]-1,3,4-Thiatriazole Derivatives Containing Pyridine Unit[J]. Chinese Journal of Applied Chemistry, ;2014, 31(12): 1419-1427. doi: 10.3724/SP.J.1095.2014.40096 shu

Synthesis and Biological Activities of 3-Aliphatic-1,2,4-Triazole[3,4-b]-1,3,4-Thiatriazole Derivatives Containing Pyridine Unit

1.
Liaoning Provincial key Laboratory of Biotechnology and Drug Discovery, School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China

Corresponding author: ZHANG Chenglu,
Received Date: 27 March 2014
Available Online: 28 May 2014
Fund Project: 辽宁省教育厅科学技术项目资助(2009A426) (2009A426)

3-Aliphatic-1,2,4-triazole derivatives 1a~1f were synthesized through the reaction of six kinds of fatty acids with diaminothiourea,in which compounds 1e and 1f were first synthesized.In the presence of phosphorus oxychloride,compounds 1a~1f reacted with 4-pyridine carboxylic acid and 2,6-pyridine dicarboxylic acid,respectively.The 12 kinds of aliphatic triazoles,thiadiazoles 2a~2f and 3a~3f were synthesized in high yields for the first time.In order to study the influence of 3-aliphatic group and pyridine,compounds 5,6,7a~7c and 8a~8c without pyridine units were also synthesized.The target compounds were well characterized by IR,¹H NMR and HRMS.In the biotic screening test,the inhibitory properties of Cdc25B and PTP1B were explored.The results show that compounds 3b,3d,3e and 3f have good inhibition activity against Cdc25B with IC₅₀ values of(1.12±0.27),(2.72±1.07),(0.72±0.05) and(4.97±0.93) mg/L,respectively;compounds 2b,3d,and 5 exhibit higher inhibition activity against PTP1B with IC₅₀ values of(0.98±0.13),(1.33±0.11),(2.18±0.20) mg/L,respectively.
- aliphatic-triazole,
- pyridine unit,
- biotic screening test,
- Cdc25B
1. [1]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
2. [2]
  Zhibei Qu , Changxin Wang , Lei Li , Jiaze Li , Jun Zhang . Organoid-on-a-Chip for Drug Screening and the Inherent Biochemistry Principles. University Chemistry, 2024, 39(7): 278-286. doi: 10.3866/PKU.DXHX202311039
3. [3]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
4. [4]
  Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
5. [5]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
6. [6]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
7. [7]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
8. [8]
  Miao-Miao Chen , Min-Ling Zhang , Xiao Song , Jun Jiang , Xiaoqian Tang , Qi Zhang , Xiuhua Zhang , Peiwu Li . Smartphone-assisted electrochemiluminescence imaging test strips towards dual-signal visualized and sensitive monitoring of aflatoxin B1 in corn samples. Chinese Chemical Letters, 2025, 36(1): 109785-. doi: 10.1016/j.cclet.2024.109785
9. [9]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
10. [10]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
11. [11]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
12. [12]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
13. [13]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
14. [14]
  Jiao CHEN , Yi LI , Yi XIE , Dandan DIAO , Qiang XIAO . Vapor-phase transport of MFI nanosheets for the fabrication of ultrathin b-axis oriented zeolite membranes. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 507-514. doi: 10.11862/CJIC.20230403
15. [15]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
16. [16]
  Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
17. [17]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
18. [18]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
19. [19]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
20. [20]
  Yuan CONG , Yunhao WANG , Wanping LI , Zhicheng ZHANG , Shuo LIU , Huiyuan GUO , Hongyu YUAN , Zhiping ZHOU . Construction and photocatalytic properties toward rhodamine B of CdS/Fe₃O₄ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2241-2249. doi: 10.11862/CJIC.20240219

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(263)
HTML views(14)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return