Citation: ZHANG Chenglu, WANG Huayu, LI Yilin, WANG Yiming, GONG Rongqing, SUN Yuedong, SONG Fulu. Synthesis of 4-Phenyl-1, 3-selenazole Derivative and Evaluation of Its Inhibitory Activity Against Protein Tyrosine Phosphatase-1B[J]. Chinese Journal of Applied Chemistry, ;2019, 36(7): 749-757. doi: 10.11944/j.issn.1000-0518.2019.07.180381 shu

Synthesis of 4-Phenyl-1, 3-selenazole Derivative and Evaluation of Its Inhibitory Activity Against Protein Tyrosine Phosphatase-1B

College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China

Corresponding author: ZHANG Chenglu, zhangchenglu@lnnu.edu.cn
Received Date: 29 November 2018
Revised Date: 4 January 2019
Accepted Date: 25 February 2019

Fund Project: Supported by the Technology Research Program of Liaoning Provincial Department of Education(No.2009A426)the Technology Research Program of Liaoning Provincial Department of Education 2009A426

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Protein tyrosine phosphatase-1B(PTP1B) is an important target for anti-diabetic treatment. That means the creation of PTP1B inhibitors with excellent activity is undoubtedly of great significance. In this paper, eleven molecules with novel structures(ZLXZ1-ZLXZ11) containing 1, 3-selenazole and 1, 2, 4-triazole active blocks were designed and synthesized. Their structures were characterized by Fourier transform infrared spectrometer(FTIR), nuclear magnetic resonance spectroscopy(NMR) and high resolution mass spectrometry(HRMS). First, ZLXZ1 and ZLXZ11 were selected for molecular docking simulation with PTP1B on MOE 2015.10. As a result, π-H action and hydrogen bonding are formed respectively between the selenium atom on the selenazole ring in ZLXZ1 and the secondary catalytic sites Tyr46 and Asp48 in PTP1B. The selenium atom on the selenazole in the ZLXZ11 molecule forms a hydrogen bond with Asp 181, which facilitates the binding of the molecule to PTP1B. On this basis, the inhibitory activities of 11 target molecules were evaluated. The results show that the inhibition rates of the target molecules are all above 87.02%, in which three target molecules are better than that of the positive control, oleanolic acid, which indicates that these novel structures are expected to be potential PTP1B inhibitors.
- 1, 3-selenazole,
- 1, 2, 4-triazole Schiff base,
- molecular docking simulation,
- protein tyrosine phosphatase-1B inhibitor
1. [1]
  Cooke D W, Plotnick L. Type 1 Diabetes Mellitus in Pediatrics[J]. Pediatr Rev, 2008,29(11):374-385. doi: 10.1542/pir.29-11-374
2. [2]
  Yip S C, Saha S, Chernoff J. PTP1B:A Double Agent in Metabolism and Oncogenesis[J]. Trends Biochem Sci, 2010,35(8):442-449. doi: 10.1016/j.tibs.2010.03.004
3. [3]
  Chen Y T, Tang C L, Ma W P. Design, Synthesis, and Biological Evaluation of Novel 2-Ethyl-5-Phenylthiazole-4-carboxamide Derivatives as Protein Tyrosine Phosphatase-1B Inhibitors with Improved Cellular Efficacy[J]. Eur J Med Chem, 2013,69:399-412. doi: 10.1016/j.ejmech.2013.09.017
4. [4]
  Omar K, Geronikaki A, Zoumpoulakis P. Novel 4-Thiazolidinone Derivatives as Potential Antifungal and Antibacterial Drugs[J]. Bioorg Med Chem, 2010,18(1):426-432. doi: 10.1016/j.bmc.2009.10.041
5. [5]
  Kline T, Felise H B, Barry K C. Substituted 2-Imino-5-Arylidenethiazolidin-4-one Inhibitors of Bacterial Type Ⅲ Secretion[J]. J Med Chem, 2008,51(22):7065-7074. doi: 10.1021/jm8004515
6. [6]
  Suresh K G V, Rajendraprasad Y, Mallikarjuna B P. Synthesis of Some Novel 2-Substituted-5-(Isopropylthiazole) Clubbed 1, 2, 4-Triazole and 1, 3, 4-oxadiazoles as Potential Antimicrobial and Antitubercular Agents[J]. Eur J Med Chem, 2010,45(5):2063-2074. doi: 10.1016/j.ejmech.2010.01.045
7. [7]
  Alsaid M S, Bashandy M S, Alqasoumi S I. Anti-breast Cancer Activity of Some Novel 1, 2-Dihydropyridine, Thiophene and Thiazole Derivatives[J]. Cheminform, 2011,42(22):137-141.
8. [8]
  Chandrappa S, Chandru H, Sharada A C. Synthesis and in Vivo Anticancer and Antiangiogenic Effects of Novel-Thioxothiazolidin-4-one Derivatives Against Transplantable Mouse Tumor[J]. Med Chem Res, 2010,19(3):236-249. doi: 10.1007/s00044-009-9187-7
9. [9]
  Garuti L, Roberti M, Pession A. Synthesis and Antiproliferative Activity of Some Thiazolylbenzimidazole-4, 7-diones[J]. Bioorg Med Chem Lett, 2001,11(24):3147-3149. doi: 10.1016/S0960-894X(01)00639-4
10. [10]
  Martin J R, Roger R J, Ernest A H, et al. 1-Dimethylcarbamoyl-3-Substituted-5-Substituted-1H-1, 2, 4-Triazoles: US, US5015652[P]. 1991.
11. [11]
  Howatt K A. Carfentrazone-Ethyl Injury to Spring Wheat Is Minimized by Some ALS-Inhibiting Herbicides1[J]. Weed Technol, 2005,19(4):777-783. doi: 10.1614/WT-04-206.1
12. [12]
  Wang B L, Liu X H, Zhang X L. Synthesis, Structure and Biological Activity of Novel 1, 2, 4-Triazole Mannich Bases Containing a Substituted Benzylpiperazine Moiety[J]. Chem Biol Drug Des, 2011,78(1):42-49. doi: 10.1111/j.1747-0285.2011.01132.x
13. [13]
  Yang B, He Q J, Zhu D Y. Antiproliferative Activity of Contragestazol(DL111-IT) in Murine and Human Tumor Models in Vitro and in Vivo[J]. Cancer Chemother Pharmacol, 2006,57(2):268-273. doi: 10.1007/s00280-005-0049-9
14. [14]
  Xia Y, Fan Z, Yao J. Discovery of Bitriazolyl Compounds as Novel Antiviral Candidates for Combating the Tobacco Mosaic Virus[J]. Cheminform, 2006,37(33):2693-2698.
15. [15]
  Xu F, Wen J, Yong B. Design and Synthesis of Novel Antifungal Triazole Derivatives with Good Activity and Water Solubility[J]. Chinese Chem Lett, 2013,24(4):303-306. doi: 10.1016/j.cclet.2013.01.047
16. [16]
  Aiken S P, Brown W M. Treatment of Epilepsy:Existing Therapies and Future Developments[J]. Front Biosci A J Virt Libr, 2000,5(1)E124. doi: 10.2741/aiken
17. [17]
  Polucci P, Magnaghi P, Angiolini M. Alkylsulfanyl-1, 2, 4-Triazoles, A New Class of Allosteric Valosine Containing Protein Inhibitors Synthesis and Structure Activity Relationships[J]. Eur J Med Chem, 2013,56(2):437-450. doi: 10.1021/jm3013213
18. [18]
  Reddy T R K, Chan L, Guo X. Design, Synthesis and SAR Exploration of Tri-substituted 1, 2, 4-Triazoles as Inhibitors of the Annexin A2 S100A10 Protein Interaction[J]. Bioorg Med Chem, 2014,22(19):5378-5391. doi: 10.1016/j.bmc.2014.07.043
19. [19]
  Bekircan O, Bektas H. Synthesis of New Bis-1, 2, 4-Triazole Derivatives[J]. Molecules, 2006,11(6):469-477. doi: 10.3390/11060469
20. [20]
  Brandt C D, Kitchen J A, Beckmann U. Synthesis and Structures of 3, 5-Disubstituted 1, 2, 4-Triazole Head Units and Incorporation of 3, 5-Dibenzoyl-1, 2, 4-Triazolate into New[J]. Supramol Chem, 2007,19(1):17-27.
21. [21]
  Lakshman B A, Gupta R L, Prasad D. Quantitative Structure Activity Relationships for the Nematicidal Activity of 4-Amino-5-Substituted Aryl-3-mercapto-(4H)-1, 2, 4-triazoles[J]. Indian J Chem, 2010,49(12):1657-1661.
22. [22]
  ZHANG Chenglu, XI Huan, SHA Yuting. Synthesis and Bioactivity of Novel Bis-heterocyclic Amide Modified Sulfide Derivatives[J]. Chinese J Appl Chem, 2017,34(3):308-315.
23. [23]
  Panda S, Nayak S. Antibacterial, Antioxidant and Anthelmintic Studies of Inclusion Complexes of Some 4-Arylidenamino-5-Phenyl-4H-1, 2, 4-Triazole-3-Thiols[J]. Supramol Chem, 2015,27(10):679-689. doi: 10.1080/10610278.2015.1075533
24. [24]
  LIU Bo, XU Caiding, ZHOU Xunjun. A Novel Synthesis of Selenourea and 2-Amino-selenazoles[J]. Chem Reagents, 1993,15(6):334-335.
25. [25]
  Rakse M, Karthikeyan C, Deora G S. Design, Synthesis and Molecular Modelling Studies of Novel 3-Acetamido-4-Methyl Benzoic Acid Derivatives as Inhibitors of Protein Tyrosine Phosphatase-1B[J]. Eur J Med Chem, 2013,70(12):469-476.
26. [26]
  ZHANG Chenglu, CHENG Anqi, TANG Jie. Synthesis and Biological of the Novel Mannich Bases of 5-Alkyl-1, 2, 4-triazole[J]. Chinese J Appl Chem, 2016,33(5):554-564.
27. [27]
  PANG Xiaobin, XIE Xinmei, WANG Shoubao. High-throughput Screening of Human Protein Tyrosine Phosphatase PTP1B Inhibitor[J]. Acta Pharm Sin, 2011,46(9):1058-1064.
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