Citation: Ren Xuanxuan, Yuan Rui, Chen Wen, Zhou Hang, Ye Fei, Shi Xueying, Hu Juan, Zhang Peng, Zhou Shengliang, Wan Yu, Wu Hui. Synthesis and Biological Evaluation of Polysubstituted 5-Amino-3, 7-diphenyl-7H-thiazolo[3, 2-a]pyrimidine-6-carbonitriles[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1266-1274. doi: 10.6023/cjoc201908007 shu

Synthesis and Biological Evaluation of Polysubstituted 5-Amino-3, 7-diphenyl-7H-thiazolo[3, 2-a]pyrimidine-6-carbonitriles

Ren Xuanxuan ^a ,
Yuan Rui ^b ,
Chen Wen ^a ,
Zhou Hang ^a ,
Ye Fei ^a ,
Shi Xueying ^a ,
Hu Juan ^a ,
Zhang Peng ^c ,
Zhou Shengliang ^b ,
Wan Yu ^b,, ,
Wu Hui ^b,,

a.
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
b.
Key Laboratory of Biotechnology for Medicinal Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou, Jiangsu 221116
c.
School of Life Science, Jiangsu Normal University, Xuzhou 221116

Corresponding author: Wan Yu, wuhui72@jsnu.edu.cn Wu Hui, 853270845@qq.com
Received Date: 5 August 2019
Revised Date: 22 October 2019
Available Online: 14 February 2020
Fund Project: the Priority Academic Program Development of Jiangsu Higher Education Institutions Third Periodthe Aid Project for Ph.D. Faculties in Jiangsu Normal University 17XLR023the Natural Science Research Projects in Universities of Jiangsu Provinc 19KJB430019the Graduate Student Scientific Research Innovation Projects in Jiangsu Province KYCX18_2116Project supported by the Priority Academic Program Development of Jiangsu Higher Education Institutions (Third Period), the Natural Science Research Projects in Universities of Jiangsu Provinc(No. 19KJB430019), the Science and Technology Foundation of Xuzhou City (No. KC19242), the Aid Project for Ph.D. Faculties in Jiangsu Normal University (No. 17XLR023) and the Graduate Student Scientific Research Innovation Projects in Jiangsu Province (Nos. KYCX18_2111, KYCX18_2116)the Science and Technology Foundation of Xuzhou City KC19242the Graduate Student Scientific Research Innovation Projects in Jiangsu Province KYCX18_2111

Figures(4)

A series of thiazolo[3, 2-a]pyrimidine derivatives were synthesized from the reaction of α-bromoacetophenone, aromatic aldehyde, malononitrile and thiourea which was catalyzed by Tröger's base derivative 5, 12-dimethyl-3, 10-diphenyl- bis-1H-pyrazol[b, f] ^{[4, 5]}-1, 5- diazadicyclo[3.3.1]-2, 6-octadiene (1). The reaction mechanism was discussed by the ¹H NMR analysis and chemical experiments. The pharmacological activity results of the products indicated that most of products showed high inhibitory on one or more cancer cells in human hepatocarcinoma cell (HepG2), human non-small cell lung cancer cell (247) and human non-small cell lung cancer cell (A549) in vitro. And seven products have antibacterial activity against the methicillin-resistant Staphylococcus aureus. These results showed the great potential of these compounds in drug development.
- Tröger's base derivative,
- catalysis,
- thiazolo[3, 2-a]pyrimidine derivative,
- anti-tumor,
- anti-bacterial
1. [1]
  Galm, U.; Wendt-Pienkowski, E.; Wang, L.; Huang, S.-X.; Unsin, C.; Tao, M.; Coughlin, J. M.; Shen, B. J. Nat. Prod. 2011, 74, 526. doi: 10.1021/np1008152
2. [2]
  (a) Pan, B.; Huang, R.; Zheng, L.; Chen, C.; Han, S.; Qu, D.; Zhu, M.; Wei, P. Eur. J. Med. Chem. 2011, 46, 819.
  (b) Samvel, N. S.; Domenico, S.; Athina, G.; Viktor, A. K.; Elmira, K. H.; Anush, A. H. Curr. Org. Chem. 2018, 22, 2576.
3. [3]
4. [4]
  Maddila, S.; Damu, G. L. V.; Oseghe, E. O.; Abafe, O. A.; Rao, C. V.; Lavanya, P. J. Korean Chem. Soc. 2012, 56, 334. doi: 10.5012/jkcs.2012.56.3.334
5. [5]
  (a) Hu, J.; Wang, Y.; Wei, X.-Y.; Wu, X.-X.; Chen, G.-Z.; Cao, G.-Z.; Shen, X.-Q.; Zhang, X.-H.; Tang, Q.-Q.; Liang, G.; Li, X.-K. Eur. J. Med. Chem. 2013, 64, 292.
  (b) Afradi, M.; Foroughifar, N.; Pasdar, H.; Moghanian, H.; Foroughifar, N. Appl. Org. Chem. 2017, 31, 3683.
6. [6]
  Mohamed, S. F.; Flefel, E. M.; Amr, A. E.-G. E.; El-Shafy, D. N. A. Eur. J. Med. Chem. 2010, 45, 1494. doi: 10.1016/j.ejmech.2009.12.057
7. [7]
  (a) El-Messery, S. M.; Hassan, G. S.; Al-Omary, F. A. M.; Ei-Sub-bagh, H. I. Eur. J. Med. Chem. 2012, 54, 615.
  (b) Abd Elhameed, A. A.; El-Gohary, N. S.; El-Bendary, E. R.; Shaaban, M. I.; Bayomi, S. M. Bioorg. Chem. 2018, 81, 299.
8. [8]
  Adib, M.; Nosrati, M.; Mahdavi, M.; Zhu, L. G.; Mirzaei, P. Synlett 2007, 2703.
9. [9]
  Jia, Y.-H.; Wang, C.-H.; Cai, D. Chemistry 2014, 77, 174.
10. [10]
  Wang, D.-L.; Wang, D.; Yan, L.; Pan, G.-Y.; Yang, J.-N. Chin. Chem. Lett. 2016, 27, 953. doi: 10.1016/j.cclet.2016.02.007
11. [11]
  Al-Omary, F A M.; Hassan, G S.; El-Messery, S M.; El-Subbagh, H I. Eur. J. Med. Chem. 2012, 47, 65. doi: 10.1016/j.ejmech.2011.10.023
12. [12]
  Yuan, R.; Wang, Y.-J.; Fang, Y.; Ge, W.-H.; Lin, W.; Li, M.-Q.; Xu, J.-B.; Wan, Y.; Liu Y.; Wu, H. Chem. Eng. J. 2017, 316, 1026. doi: 10.1016/j.cej.2017.02.026
13. [13]
  Paul, A.; Maji, B.; Misra, S. K.; Jain, A. K.; Muniyappa, K.; Bhattacharya, S. J. Med. Chem. 2012, 55, 7460. doi: 10.1021/jm300442r
14. [14]
  Kejik, Z.; Briza, T.; Havlik, M.; Dolensky, B.; Kaplanek, R.; Kralova, J.; Mikula, I.; Martasek, P.; Kral, V. Dyes Pigm. 2016, 134, 212. doi: 10.1016/j.dyepig.2016.07.002
15. [15]
  (a) Ishiwari, F.; Takeuchi, N.; Sato, T.; Yamazaki, H.; Osuga, R.; Kondo, J. N.; Fukushima, T. ACS Macro Lett. 2017, 6, 775.
  (b) Xiao, Y.; Zhang, L.; Xu, L.; Chung, T.-S. J. Membr. Sci. 2017, 521, 65.
  (c) Zou, X.; Zhu, G. Adv. Mater. 2018, 30.
16. [16]
  (a) Sergeyev, S.; Didier, D.; Boitsov, V.; Teshome, A.; Asselberghs, I.; Clays, K.; Velde, C. M. L. V.; Plaquet, A.; Champagne, B. Chem.-Eur. J. 2010, 16, 8181.
  (b) Xi, H.; Liu, Y.; Yuan, C.-X.; Li, Y.-X.; Wang, L.; Tao, X.-T.; Ma, X.-H.; Zhang, C.-F.; Hao, Y. RSC Adv. 2015, 5, 45668.
17. [17]
  (a) Elmes, R. B. P.; Erby, M.; Bright, S. A.; Williams, D. C.; Gunnlaugsson, T. Chem. Commun. 2012, 48, 2588.
  (b) Wu, Z.; Tang, M.; Tian, T.; Wu, J.; Deng, Y.; Dong, X.; Tan, Z.; Weng, X.; Liu, Z.; Wang, C.; Zhou, X. Talanta 2011, 87, 216.
  (c) Calatrava-Pérez, E.; Delente, J. M.; Shanmugaraju, S.; Hawes, C. S.; Williams, C. D.; Gunnlaugsson, T.; Scanlan, E. M. Org. Bio-mol. Chem. 2019, 17, 2116.
18. [18]
  Yuan, R.; Li, M.-Q.; Xu, J.-B.; Huang, S.-Y.; Zhou, S.-L.; Zhang, P.; Liu, J.-J.; Wu, H. Tetrahedron 2016, 72, 4081. doi: 10.1016/j.tet.2016.05.042
19. [19]
  (a) Cabrero-Antonino, J. R.; García, T.; Rubio-Marqués, P.; Vidal-Moya, J. A.; Leyva-Pérez, A.; Al-Deyab, S. S.; Al-Resayes, S. I.; Díaz, U.; Corma, A. ACS Catal. 2011, 1, 147.
  (b) Pereira, R.; Cvengroš, J. Eur. J. Org. Chem. 2013, 2013, 4233.
  (c) Wu, H.; Chen, X.-M.; Wan, Y.; Ye, L.; Xin, H.-M.; Xu, H.-H.; Yue, C.-H.; Pang, L.-L.; Ma, R.; Shi, D.-Q. Tetrahedron Lett. 2009, 50, 1062.
  (d) Youssef, A. M. S.; Fouda, A. M.; Faty, R. M. Chem. Cent. J. 2018, 12, 50.
20. [20]
  (a) Yuan, R.; Ren, X. X.; Zhang, P.; Chen, W.; Zhou, H.; Wan, Y.; Wu, H. CN 110013483, 2019.
  (b) Wan, Y.; Ren, X. X.; Zhang, P.; Yuan, R.; Chen, W.; Zhou, H.; Wu, H. CN 110041348, 2019.
1. [1]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
2. [2]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
3. [3]
  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
4. [4]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
5. [5]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
6. [6]
  Fa Wang , Yu Chen , Hui Chao . Ruthenium(II) Complexes as Photoactivated Chemo-Prodrugs for Hypoxic Tumor Therapy. University Chemistry, 2025, 40(7): 200-212. doi: 10.12461/PKU.DXHX202410024
7. [7]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
8. [8]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
9. [9]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
10. [10]
  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
11. [11]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
12. [12]
  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
13. [13]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
14. [14]
  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
15. [15]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
16. [16]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
17. [17]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-0. doi: 10.3866/PKU.WHXB202406007
18. [18]
  Xinlong XU , Chunxue JING , Yuzhen CHEN . Bimetallic MOF-74 and derivatives: Fabrication and efficient electrocatalytic biomass conversion. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1545-1554. doi: 10.11862/CJIC.20250046
19. [19]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
20. [20]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(1395)
HTML views(167)

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