Citation: Peng ZHANG, Xiao-Mei ZHAO. Synthesis, Crystal Structure and Bioactivity Evaluation of a Heterocyclic Compound[J]. Chinese Journal of Structural Chemistry, ;2020, 39(10): 1892-1897. doi: 10.14102/j.cnki.0254–5861.2011–2682 shu

Synthesis, Crystal Structure and Bioactivity Evaluation of a Heterocyclic Compound

Peng ZHANG ^, ,
Xiao-Mei ZHAO

School of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, Shaanxi 712046, China

Corresponding author: Peng ZHANG, peng_zhang11@126.com
Received Date: 2 December 2019
Accepted Date: 12 February 2020

Figures(5)

The heterocyclic compound 2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (1), designed using 2-chloro-6-methylaniline (2) as the start material, was successfully obtained via multiple synthesis route and finally characterized by IR, ¹H NMR, and single-cystal X-ray crystallography. To select the suitable candidates for tissue regeneration, the induction activity of the compound on the dental pulp mesenchymal stem cells (DP-MSCs) was evaluated. Firstly, the DP-MSCs cells were isolated and the cell colon formation ability was measured after compound treatment with cell colony determination. After that, the RT-PCT assay was conducted and the relative expression level of the genes related with cell osteogenesis and proliferation was further detected.
- heterocycles,
- X-ray,
- DP-MSCs,
- RT-PCT assay
1. [1]
  Terunuma, A.; Ashiba, K.; Takane, T.; Sakaguchi, Y.; Terunuma, H. Comparative transcriptomic analysis of human mesenchymal stem cells derived from dentalpulp and adipose tissues. J. Stem. Cells Regen. Med. 2019, 15, 8–11.
2. [2]
  Tang, X.; Li, W.; Wen, X.; Zhang, Z.; Chen, W.; Yao, G.; Chen, H.; Wang, D.; Shi, S.; Sun, L. Transplantation of dental tissue-derived mesenchymal stem cells ameliorates nephritis in lupus mice. Ann. Transl. Med. 2019, 7, 132. doi: 10.21037/atm.2019.02.41
3. [3]
  Jin, Q.; Yuan, K.; Lin, W.; Niu, C.; Ma, R.; Huang, Z. Comparative characterization of mesenchymal stem cells from human dental pulp and adipose tissue for bone regeneration potential. Artif. Cells Nanomed. Biotechnol. 2019, 47, 1577–1584. doi: 10.1080/21691401.2019.1594861
4. [4]
  Vahedi, P.; Jarolmasjed, S.; Shafaei, H.; Roshangar, L.; Soleimani Rad, J.; Ahmadian, E. In vivo articular cartilage regeneration through infrapatellar adipose tissue derived stem cellin nanofiber polycaprolactone scaffold. Tissue Cell 2019, 57, 49 – 56. doi: 10.1016/j.tice.2019.02.002
5. [5]
  Dave, J. R.; Tomar, G. B. Dental tissue-derived mesenchymal stem cells: applications in tissue engineering. Crit. Rev. Biomed. Eng. 2018, 46, 429–468.
6. [6]
  Xing, Y.; Zhang, Y.; Wu, X.; Zhao, B.; Ji, Y.; Xu, X. A comprehensive study on donor-matched comparisons of three types of mesenchymal stem cells-containing cells from human dental tissue. J. Periodontal Res. 2019, 54, 286–299. doi: 10.1111/jre.12630
7. [7]
  Nakaya, A.; Fujita, S.; Satake, A.; Nakanishi, T.; Azuma, Y.; Tsubokura, Y.; Hotta, M.; Yoshimura, H.; Ishii, K.; Ito, T.; Nomura, S. Clinical significance of dasatinib-induced pleural effusion in patients with de novochronic myeloid leukemia. Hematol. Rep. 2018, 10, 7474.
8. [8]
  Naqvi, K.; Kantarjian, H. M. Reply to starting with a lower daily dose of dasatinib in patients with chronic myeloid leukemia in chronic phase: less is more, or is it? Cancer 2018, 124, 4261. doi: 10.1002/cncr.31683
9. [9]
  Wehrstedt, S.; Kubis, J.; Zimmermann, A.; Bruns, H.; Mayer, D.; Grieshober, M.; Stenger, S. The tyrosine kinase inhibitor dasatinib reduces the growth of intracellular Mycobacterium tuberculosis despite impairing T-cell function. Eur. J. Immunol. 2018, 48, 1892–1903. doi: 10.1002/eji.201847656
10. [10]
  Sheldrick, G. M. SHELXL-97, Program for Solution Crystal Structure and Refinement. University of Göttingen: Göttingen, Germany 1997.
11. [11]
  Igarashi, Y.; Chosa, N.; Sawada, S.; Kondo, H.; Yaegashi, T.; Ishisaki, A. VEGF-C and TGF-β reciprocally regulate mesenchymal stem cell commitment to differentiation into lymphatic endothelial or osteoblastic phenotypes. Int. J. Mol. Med. 2016, 37, 1005–1013. doi: 10.3892/ijmm.2016.2502
12. [12]
  Ajlan, S. A.; Ashri, N. Y.; Aldahmash, A. M.; Alnbaheen, M. S. Osteogenic differentiation of dental pulp stem cells under the influence of three different materials. BMC Oral Health 2015, 15, 132. doi: 10.1186/s12903-015-0113-8
13. [13]
  Liu, W.; Zhou, J.; Zheng, Y.; Qi, F.; Zhang, H.; Qian, H.; Wang, J.; Cheng, Y.; Gust, R. Design, synthesis and antiproliferative activity of 2-acetamidothiazole-5-carboxamide derivatives. Med. Chem. 2012, 8, 587–594. doi: 10.2174/157340612801216418
14. [14]
  Singh, K. S.; Devi, P.; Sawant, S. G.; Kaminsky, W. Arene ruthenium(II) complexes with 2-acetamidothiazole derived ligands: synthesis, structural studies, antifouling and antibacterial properties. Polyhedron 2015, 100, 321–325. doi: 10.1016/j.poly.2015.08.016
15. [15]
  Hatfield, J. M.; Eidell, C. K.; Stephens, C. E. Mono- and trifluorination of the thiazole ring of 2, 5-diarylthiazoles using N-fluorobenzenesulfonimide (NFSI). Tetra. Lett. 2013, 54, 1025–1028. doi: 10.1016/j.tetlet.2012.12.052
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