Synthesis and anticancer activities of diverse furo[2,3-d]pyrimidine and benzofuro[3,2-d]pyrimidine derivatives

被引:6
作者
Tang, Xiaoyu [1 ,2 ,3 ]
Zheng, Aihua [1 ,2 ,3 ]
Wu, Fengxu [1 ,2 ,3 ]
Liao, Chujie [1 ,2 ,3 ]
Hu, Yanggen [1 ,2 ,3 ]
Luo, Chao [1 ,2 ,4 ]
机构
[1] Hubei Univ Med, Sch Pharmaceut Sci, Shiyan, Peoples R China
[2] Hubei Univ Med, Inst Med Chem, Shiyan, Peoples R China
[3] Hubei Univ Med, Hubei Key Lab Wudang Local Chinese Med Res, Shiyan, Peoples R China
[4] Hubei Univ Med, Sch Basic Med Sci, Shiyan, Peoples R China
关键词
Antitumor; Aza-Wittig reaction; benzofuro[3; 2-d]pyrimidine; furo[2; 3-d]pyrimidine; molecular docking; synthesis; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; MOLECULAR-DYNAMICS; INHIBITORS; DISCOVERY; KINASE;
D O I
10.1080/00397911.2022.2060117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of diverse furo[2,3-d]pyrimidines (2a-2b, 4a-4d and 8a-8c) and benzofuro[3,2-d]pyrimidines (12a-12c) were synthesized and screened for their antitumor effects against HepG2, Bel-7402 and HeLa cell lines in vitro. Representatively, 4a, with an IC50 of 0.70 mu M, exhibited the best antitumor activity against the tested HepG2 cell lines. Molecular docking investigation further revealed the possible binding modes of compound 4a with receptor tyrosine kinase. Preliminary results indicated that the title compounds were helpful as leading structures for preparing a new antitumor drug.
引用
收藏
页码:994 / 1003
页数:10
相关论文
共 50 条
  • [31] Design, synthesis, and evaluation of the anticonvulsant and antidepressant activities of pyrido[2,3-d]pyrimidine derivatives
    Hong-Jian Zhang
    Shi-Ben Wang
    Xiang Wen
    Jin-Zi Li
    Zhe-Shan Quan
    Medicinal Chemistry Research, 2016, 25 : 1287 - 1298
  • [32] Synthesis, biological activity, and in silico studies of thieno[2,3-d]pyrimidine and thieno[2,3-d]triazine derivatives
    El-Hag, Fatma A. A.
    Elrashedy, Ahmed A.
    Sweed, Ayman M. K.
    Ewies, Ewies F.
    Abd-El-Maksoud, Mansoura A.
    Aly, Magdy S.
    Atta, Sanaa M. Sh.
    EGYPTIAN PHARMACEUTICAL JOURNAL, 2022, 21 (03) : 360 - 375
  • [33] Design, synthesis and biological evaluation of novel 2,4-bismorpholinothieno[3,2-d ]pyrimidine and 2-morpholinothieno[3,2-d] pyrimidinone derivatives as potent antitumor agents
    Ye, Tianyu
    Han, Yufei
    Wang, Ruxin
    Yan, Pingzhen
    Chen, Shaowei
    Hou, Yunlei
    Zhao, Yanfang
    BIOORGANIC CHEMISTRY, 2020, 99
  • [34] Design, Synthesis and Biological Evaluation of Pyrido[2,3-d] Pyrimidine Derivatives as Potential Anticancer Agents
    Al-Otaibi, Jamelah S.
    Ibrahim, Diaa A.
    El Gogary, Tarek M.
    LETTERS IN DRUG DESIGN & DISCOVERY, 2018, 15 (12) : 1240 - 1251
  • [35] SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME SUBSTITUTED PYRIDO [3′,2′: 4,5] FURO [2,3-d] PYRIMIDINE DERIVATIVES
    Godhani, D. R.
    Kaila, B. K.
    Sanghani, A. M.
    Dobariya, P. B.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 22 (03) : 253 - 258
  • [36] A facile clean synthesis of pyrido [2,3-d] pyrimidine and their derivatives in ionic liquids
    Yadav, Ashok K.
    Gupta, Manisha
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2014, 53 (10): : 1247 - 1254
  • [37] Multicomponent Synthesis of the Medicinally Important Pyrrolo[2,3-d]Pyrimidine Scaffold (Minireview)
    Dasari, R.
    Kornienko, A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (02) : 139 - 144
  • [38] Synthesis of various pharma based pyrido[2,3-d]pyrimidine as well as pyrido[1,2-a]pyrimidine and their antimicrobial activities
    Rana, Pragnesh B.
    Patel, Jigisha A.
    Mistry, B. D.
    Desai, K. R.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2010, 87 (03) : 365 - 372
  • [39] Synthesis and Evaluation of Biological and Antitumor Activities of Tetrahydrobenzothieno[2,3-d]Pyrimidine Derivatives as Novel Inhibitors of FGFR1
    Wang, Xuebao
    Chen, Di
    Yu, Shufang
    Zhang, Zaikui
    Wang, Yu
    Qi, Xiaolu
    Fu, Weitao
    Xie, Zixin
    Ye, Faqing
    CHEMICAL BIOLOGY & DRUG DESIGN, 2016, 87 (04) : 499 - 507
  • [40] Design, synthesis, anticancer evaluation, and in silico studies of some thieno[2,3-d]pyrimidine derivatives as EGFR inhibitors
    Sayed, Menna Tallah M.
    Halim, Peter A.
    El-Ansary, Afaf K.
    Hassan, Rasha A.
    DRUG DEVELOPMENT RESEARCH, 2023, 84 (06) : 1299 - 1319