Citation: KOU Lidong, WANG Wei. Synthesis and Antitumor Activity of Tetrahydroimidazo[2', 1':2, 3]thiazolo[5, 4-c]piperdine Derivatives[J]. Chinese Journal of Applied Chemistry, ;2017, 34(8): 905-911. doi: 10.11944/j.issn.1000-0518.2017.08.160420 shu

Synthesis and Antitumor Activity of Tetrahydroimidazo[2', 1':2, 3]thiazolo[5, 4-c]piperdine Derivatives

KOU Lidong ,
WANG Wei ^,

School of Chemistry and Chemical Engineering, He'nan Engineering Laboratory of Chemical Pharmaceutical and Biomedical Materials, He'nan Normal University, Xinxiang, He'nan 453007, China

Corresponding author: WANG Wei, weiwang161718@163.com
Received Date: 18 October 2016
Revised Date: 27 December 2017
Accepted Date: 28 March 2017

Fund Project: Supported by the Scientific and Technological Projects of Henan Province(No.122107000014)the Scientific and Technological Projects of Henan Province No.122107000014

Figures(1)

A series of novel 5, 6, 7, 8-tetrahydroimidazo[2', 1':2, 3]thiazolo[5, 4-c]piperidines was synthesized through sequential amino protection, condensation, cyclization, and deprotection reactions using piperidone as the raw material. The structures of these compounds were confirmed by proton or carbon nuclear magnetic resonance(¹H NMR, ¹³C NMR), mass spectrometry(MS) and elemental analysis. The antitumor activities of these compounds were evaluated in vitro, and the results indicated that these compounds had certain inhibitory activities against MCF-7 human breast cancer cells, and the inhibitory activity of compound 5a reached the level of strong potency with the half maximal inhibitory concentration(IC₅₀) value of 8.6 μmol/L. It provides a reference for the antitumor activity of such compounds.
- tetrahydroimidazo[2', 1':2, 3]thiazolo[5, 4-c]piperidine,
- derivatives,
- antitumor
1. [1]
  WANG Guoqiang, DUAN Nannan, CAO Tieyao. Antitumor Fluoroquinolone C3-Isostere Derivatives(Ⅰ)-Synthesis and Activity of Bis-oxadiazole Methyl-Sulfide Derivatives[J]. Chinese J Appl Chem, 2012,29(7):769-774.
2. [2]
  Ma H, Lu W, Sun Z. Design, Synthesis, and Structure-Activity-Relationship of Tetrahydrothiazolopyridine Derivatives as Potent Smoothened Antagonists[J]. Eur J Med Chem, 2015,89:721-732. doi: 10.1016/j.ejmech.2014.11.006
3. [3]
  Ng J M, Curran T. The Hedgehog's Tale:Developing Strategies for Targeting Cancer[J]. Nat Rev Cancer, 2011,11(7):493-501. doi: 10.1038/nrc3079
4. [4]
  Alessandro F, Francesco C, Andrea K. Identification of New Aminoacid Amides Containing the Imidazo-[J]. Eur J Med Chem, 2012,47:239-254. doi: 10.1016/j.ejmech.2011.10.051
5. [5]
  Lucas B S, Aaron W, An S. Design of 1-Piperazinyl-4-Arylphthalazines as Potent Smoothened Antagonists[J]. Bioorg Med Chem Lett, 2010,20(12):3618-3622. doi: 10.1016/j.bmcl.2010.04.110
6. [6]
  Aronov A M, Baker C, Bemis G W. Flipped Out:Structure-Guided Design of Selective Pyrazolylpyrrole ERK Inhibitors[J]. J Med Chem, 2007,50(6):1280-1287. doi: 10.1021/jm061381f
7. [7]
  Yang Y, Engkvist O, Llinàs A. Beyond Size, Ionization State, and Lipophilicity:Influence of Molecular Topology on Absorption, Distribution, Metabolism, Excretion, and Toxicity for Druglike Compounds[J]. J Med Chem, 2012,55(8):3667-3677. doi: 10.1021/jm201548z
8. [8]
  Munshi N, Jeay S, Li Y. ARQ197, A Novel and Selective Inhibitor of the Human C-Met Receptor Tyrosine Kinase with Antitumor Activity[J]. Mol Cancer Ther, 2010,9(6):1544-1553. doi: 10.1158/1535-7163.MCT-09-1173
9. [9]
  D'Angelo N D, Bellon S F, Booker S K. Design, Synthesis, and Biological Evaluation of Potent c-Met Inhibitors[J]. J Med Chem, 2008,51(18):5766-5779. doi: 10.1021/jm8006189
10. [10]
  Allegretti P A, Ferreira E M. Platinum-Catalyzed Cyclizations via Carbene Intermediates:Syntheses of Complementary Positional Isomers of Isoxazoles[J]. Chem Sci, 2013,4(3):1053-1058. doi: 10.1039/C2SC21671J
11. [11]
  Zhuo W, Erin J M, Samantha J S. Modular Synthesis of Functionalized Bis-bispidine Tetraazamacrocycles[J]. Org Lett, 2011,13(24):6540-6543. doi: 10.1021/ol202840s
12. [12]
  YANG Ruisheng, HU Guoqiang, XIE Songqiang. Synthesis and Antitumor Activity of 3-Methylthio-4-amino-5-pyridin-3-yl-1, 2, 4-triazole Schiff Bases[J]. Chinese J Appl Chem, 2008,25(7):783-786.
13. [13]
  LUO Wen, LI Zhan, ZHAI Yangyang. Synthesis and Antitumor Activity of Polyamine Derivatives of Naphthalimide[J]. Chinese J Appl Chem, 2013,30(3):265-270.
1. [1]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
2. [2]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
3. [3]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
4. [4]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . 高效靶向示踪钙钛矿纳米系统光电增效抗肿瘤. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-. doi: 10.1016/j.actphy.2024.100042
5. [5]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
6. [6]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
7. [7]
  Min LI , Xianfeng MENG . Preparation and microwave absorption properties of ZIF-67 derived Co@C/MoS₂ nanocomposites. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1932-1942. doi: 10.11862/CJIC.20240065
8. [8]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
9. [9]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
10. [10]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
11. [11]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
12. [12]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
13. [13]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
14. [14]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
15. [15]
  Tingting XU , Wenjing ZHANG , Yongbo SONG . Research advances of atomic precision coinage metal nanoclusters in tumor therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2275-2285. doi: 10.11862/CJIC.20240229
16. [16]
  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
17. [17]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
18. [18]
  Jiahui CHEN , Tingting ZHENG , Xiuyun ZHANG , Wei LÜ . Research progress of near-infrared absorption inorganic nanomaterials in photothermal and photodynamic therapy of tumors. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2396-2414. doi: 10.11862/CJIC.20240106
19. [19]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
20. [20]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(509)
HTML views(64)

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