Advanced Search

Citation: Hua Chen, Shun-Kai Xing, Fang Gao, Na Li, Xiao-Liu Li, Ming Meng. Design, synthesis and immunomodulating activity of C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond[J]. Chinese Chemical Letters, ;2016, 27(6): 938-942. doi: 10.1016/j.cclet.2016.01.041 shu

Design, synthesis and immunomodulating activity of C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond

Hua Chen ^a, ,
Shun-Kai Xing ^a ,
Fang Gao ^a ,
Na Li ^b ,
Xiao-Liu Li ^a ,
Ming Meng ^b

a Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China;
b Medical School, Hebei University, Baoding 071002, China

Received Date: 2 November 2015
Revised Date: 3 December 2015

Fund Project: The financial supports from the National Natural Science Foundation of China (Nos. 20972039, 21372060), Research Fund for the Doctoral Program of Higher Education of China (No. 20121301110004), Hebei Province Natural Science Fund for Distinguished Young Scholars (No. B2015201005), the Medicinal Joint Funds of the Natural Science Foundation of Hebei and Shijiazhuang Pharmaceutical Group Foundation (No. B2011201169), and the Natural Science Foundations of Education Department of Hebei (No. ZH2011110).

Several novel C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond were rationally designed and easily synthesized at room temperature by using the unprotected sugar aldehyde as the starting material. The effects of the compounds on Con A-induced T cell proliferation were evaluated at five concentrations of 5, 10, 25, 50, and 100 mmol/L Interestingly, compounds 7a and 8a (n = 2, R = H) exhibited immunostimulating activities, while compounds 5a, 6a (n = 1, R = H) and 7b, 8b (n = 2,R = CH₃) showed immunosuppressive activities. Another two compounds 5b and 6b (n = 1,R = CH3) had no immunomodulating activities. These initial biological results suggested that subtle structural changes to the phenyl and acetamide bond of C-pseudonucleosides could have a significant effect on T cell proliferation bias, although it was difficult to formulate a rigorous structureactivity relationship based on the observed activities.
- Immunomodulator,
- C-Pseudonucleosides,
- Thiazolidin-4-one,
- Acetamide bond,
- SAR analysis
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
1. [1]
  Mianying Huang , Zhiguang Xu , Xiaoming Lin . Mechanistic analysis of Co2VO4/X (X = Ni, C) heterostructures as anode materials of lithium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100309-100309. doi: 10.1016/j.cjsc.2024.100309
2. [2]
  Xiaodong Zhang , Bohui Xu , Deshuai Xiao , Xinyuan Zhang , Pifu Gong , Zheshuai Lin . From centrosymmetric CN3H6C6H5SO3 to non-centrosymmetric CN3H6C6H4SO3(OH): Hydroxyl introduced hydrogen bond reconstruction to realize strong second harmonic generation. Chinese Journal of Structural Chemistry, 2025, 44(10): 100707-100707. doi: 10.1016/j.cjsc.2025.100707
3. [3]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
4. [4]
  Tian-Zhang Wang , Le-Yu Tang , Yu-Qiu Guan , Lingfei Hu , Gang Lu , Yu-Feng Liang . Nickel-catalyzed reductive alkynylation of ketoimines via unstrained C–C bond activation. Chinese Chemical Letters, 2025, 36(11): 111050-. doi: 10.1016/j.cclet.2025.111050
5. [5]
  Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
6. [6]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
7. [7]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
8. [8]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
9. [9]
  Yang Li , Yanan Dong , Zhihong Wei , Changzeng Yan , Zhen Li , Lin He , Yuehui Li . Fluoride-promoted Ni-catalyzed cyanation of C–O bond using CO₂ and NH₃. Chinese Chemical Letters, 2025, 36(5): 110206-. doi: 10.1016/j.cclet.2024.110206
10. [10]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
11. [11]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
12. [12]
  Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
13. [13]
  Yang Qin , Jiangtian Li , Xuehao Zhang , Kaixuan Wan , Heao Zhang , Feiyang Huang , Limei Wang , Hongxun Wang , Longjie Li , Xianjin Xiao . Toeless and reversible DNA strand displacement based on Hoogsteen-bond triplex. Chinese Chemical Letters, 2024, 35(5): 108826-. doi: 10.1016/j.cclet.2023.108826
14. [14]
  Jun-Gang Wang , Bing-Yi Zhou , Yao-Luo Hu , Yong-Dong Du , Rong-He Wu , Chun-Yan Wu , Wen-Chao Yang , An-Xin Wu . Atom-swapping skeletal editing of benzo[c]oxepines for the construction of 2-benzodiazepines via a continuous manufacturing one-pot synthesis. Chinese Chemical Letters, 2026, 37(4): 111200-. doi: 10.1016/j.cclet.2025.111200
15. [15]
  Neng Shi , Haonan Jia , Jixiang Zhang , Pengyu Lu , Chenglong Cai , Yixin Zhang , Liqiang Zhang , Nongyue He , Weiran Zhu , Yan Cai , Zhangqi Feng , Ting Wang . Accurate expression of neck motion signal by piezoelectric sensor data analysis. Chinese Chemical Letters, 2024, 35(9): 109302-. doi: 10.1016/j.cclet.2023.109302
16. [16]
  Yuxin Li , Chengbin Liu , Qiuju Li , Shun Mao . Fluorescence analysis of antibiotics and antibiotic-resistance genes in the environment: A mini review. Chinese Chemical Letters, 2024, 35(10): 109541-. doi: 10.1016/j.cclet.2024.109541
17. [17]
  Zixuan Chen , Yafeng Wu , Zhaoyan Tian , Zhaohan Wang , Weiwei Liu , Songqin Liu . A reproducible hybrid membrane for in situ analysis of cell secretions with a wide size range. Chinese Chemical Letters, 2025, 36(12): 110917-. doi: 10.1016/j.cclet.2025.110917
18. [18]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
19. [19]
  Chuanjian Cui , Zhuang Liu , Shiyu Yang , Qiang Wei , Jiahui Ding , Ziyang Xu , Changyong Zhang . Performance analysis of membrane capacitive deionization (MCDI): The relative insensitivity to feedwater temperatures. Chinese Chemical Letters, 2026, 37(2): 111342-. doi: 10.1016/j.cclet.2025.111342
20. [20]
  Yanhui Zhong , Peisi Xie , Chengyi Xie , Lei Guo , Weiwei Chen , Shuyi Wang , Xiaoxiao Wang , Fuyue Wang , Zian Lin , Gongke Li , Zongwei Cai . Rigid urea-based structures drive analysis of chiral amino acids. Chinese Chemical Letters, 2026, 37(2): 112039-. doi: 10.1016/j.cclet.2025.112039

Metrics

PDF Downloads(0)
Abstract views(1395)
HTML views(28)

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

Powered By info@rhhz.net

/

DownLoad: Full-Size Img PowerPoint