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
1. [1]
  Hongwei Ma , Fang Zhang , Hui Ai , Niu Zhang , Shaochun Peng , Hui Li . Integrated Crystallographic Teaching with X-ray,TEM and STM. University Chemistry, 2024, 39(3): 5-17. doi: 10.3866/PKU.DXHX202308107
2. [2]
  Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
3. [3]
  Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
4. [4]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
5. [5]
  Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
6. [6]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
7. [7]
  Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
8. [8]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
9. [9]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
10. [10]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
11. [11]
  Ruike Hu , Kangmin Wang , Junxiang Liu , Jingxian Zhang , Guoliang Yang , Liqiu Wan , Bijin Li . Extended π-conjugated systems by external ligand-assisted C−H olefination of heterocycles: Facile access to single-molecular white-light-emitting and NIR fluorescence materials. Chinese Chemical Letters, 2025, 36(4): 110113-. doi: 10.1016/j.cclet.2024.110113
12. [12]
  Huan Yao , Jian Qin , Yan-Fang Wang , Song-Meng Wang , Liu-Huan Yi , Shi-Yao Li , Fangfang Du , Liu-Pan Yang , Li-Li Wang . Ultra-highly selective recognition of nucleosides over nucleotides by rational modification of tetralactam macrocycle and its application in enzyme assay. Chinese Chemical Letters, 2024, 35(6): 109154-. doi: 10.1016/j.cclet.2023.109154
13. [13]
  Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO₄⁻, ReO₄⁻). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
14. [14]
  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
15. [15]
  Shenhao QIU , Qingquan XIAO , Huazhu TANG , Quan XIE . First-principles study on electronic structure, optical and magnetic properties of rare earth elements X (X=Sc, Y, La, Ce, Eu) doped with two-dimensional GaSe. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2250-2258. doi: 10.11862/CJIC.20240104
16. [16]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
17. [17]
  Wei Li , Guoqiang Feng , Ze Chang . Teaching Reform of X-ray Diffraction Using Synchrotron Radiation in Materials Chemistry. University Chemistry, 2024, 39(3): 29-35. doi: 10.3866/PKU.DXHX202308060
18. [18]
  Hongwei Ma , Hui Li . Three Methods for Structure Determination from Powder Diffraction Data. University Chemistry, 2024, 39(3): 94-102. doi: 10.3866/PKU.DXHX202310035
19. [19]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
20. [20]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(288)
HTML views(12)

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