Facile synthesis and antitumor activity of novel 2-trifluoromethylthieno[2, 3-d]pyrimidine derivatives

Chinese Chemical Letters

Volumn 25, Issue 7, 2014, Pages 1006-1010

  Song, Xin Jian ^a   Yang, Ping ^a   Gao, Hui ^a   Wang, Yan ^a   Dong, Xing Gao ^a   Tan, Xiao Hong ^a  

^a HUBEI UNIVERSITY FOR NATIONALITIES   (China)

Author keywords

Antitumor activity; Facile synthesis; Gewald reaction; Thieno 2,3 d pyrimidine; Trifluoromethyl

Indexed keywords

EID: 84905648559     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2014.05.043     Document Type: Article

References (29)

1. R. Adepu, D. Rambabu, and B. Prasad et al. Novel thieno[2,3-d] pyrimidines: their design, synthesis, crystal structure analysis and pharmacological evaluation Org. Biomol. Chem. 10 2012 5554 5569
2. J.G. Paez, P.A. Janne, and J.C. Lee et al. EGFR mutations in lung cancer: correlation with clinical response to gefitinib therapy Science 304 2004 1497 1500
3. B. Higgins, K. Kolinsky, and M. Smith et al. Antitumor activity of erlotinib (OSI-774, Tarceva) alone or in combination in human non-small cell lung cancer tumor xenograft models Anticancer Drugs 15 2004 503 512
4. Z.A. Liu, A. Fusi, and A. Schmittel et al. Eradication of EGFR-positive circulating tumor cells and objective tumor response with lapatinib and capecitabine Cancer Biol. Ther. 10 2010 860 864
5. Y. Dai, Y. Guo, and R.R. Frey et al. Thienopyrimidine ureas as novel and potent multitargeted receptor tyrosine kinase inhibitors J. Med. Chem. 48 2005 6066 6083
6. J.C. Aponte, A.J. Vaisberg, and D. Castillo et al. Trypanoside, anti-tuberculosis, leishmanicidal, and cytotoxic activities of tetrahydrobenzothienopyrimidines Bioorg. Med. Chem. 18 2010 2880 2886
7. N.S. Habib, R. Soliman, A.A. El-Tombary, S.A. El-Hawash, and O.G. Shaaban Synthesis and biological evaluation of novel series of thieno[2,3-d]pyrimidine derivatives as anticancer and antimicrobial agents Med. Chem. Res. 22 2013 3289 3308
8. B.Q. Cai, H.X. Jin, X.J. Yan, P. Zhu, and G.X. Hu 3D-QSAR and 3D-QSSR studies of thieno[2,3-d]pyrimidin-4-yl hydrazone analogues as CDK4 inhibitors by CoMFA analysis Acta Pharmacol. Sin. 35 2014 151 160
9. W.K. Hagmann The many roles for fluorine in medicinal chemistry J. Med. Chem. 51 2008 4359 4369
10. X.J. Song, Z.C. Duan, Y. Shao, and X.G. Dong Facile synthesis of novel fluorinated thieno[2,3-d]pyrimidine derivatives containing 1,3,4-thiadiazole Chin. Chem. Lett. 23 2012 549 552
11. T. Horiuchi, M. Nagata, M. Kitagawa, K. Akahane, and K. Uoto Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of Cyclin D1-CDK4: synthesis, biological evaluation and structure-activity relationships. Part 2 Bioorg. Med. Chem. Lett. 17 2009 7850 7860
12. A.G. Golub, V.G. Bdzohla, and N.V. Briukhovetska et al. Synthesis and biological evaluation of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2 Eur. J. Med. Chem. 46 2011 870 876
13. T. Beckers, A. Sellmer, and E. Eichhorn et al. Novel inhibitors of epidermal growth factor receptor: (4-(arylamino)-7H-pyrrolo[2,3-d]pyrimidin-6- yl)(1H-indol-2-yl)methanones and (1H-indol-2-yl)(4-(phenylamino)thieno[2,3-d] pyrimidin-6-yl)methanones Bioorg. Med. Chem. 20 2012 125 136
14. S.E. Abbas, N.M.A. Gawad, R.F. George, and Y.A. Akar Synthesis, antitumor and antibacterial activities of some novel tetrahydrobenzo[4,5]thieno[2,3-d] pyrimidine derivatives Eur. J. Med. Chem. 65 2013 195 204
15. P. Yang, Y. Wang, and Z.C. Duan et al. Synthesis, crystal structure, and biological activity of 4-chlorobenzaldehyde (2-trifluoromethyl-5,6,7,8- tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)hydrazone monohydrate Chin. J. Struct. Chem. 32 2013 1023 1030
16. T. Horiuchi, J. Chiba, K. Uoto, and T. Soga Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of Cyclin D1-CDK4: synthesis, biological evaluation, and structure-activity relationships Bioorg. Med. Chem. Lett. 19 2009 305 308
17. 2A receptor. Part 1: discovery and synthesis of thieno[3,2-d]pyrimidine-4-methanone derivatives Bioorg. Med. Chem. Lett. 18 2008 2916 2919
18. M. Hayakawa, H. Kaizawa, and H. Moritomo et al. Synthesis and biological evaluation of 4-morpholino-2-phenylquinazolines and related derivatives as novel PI3 kinase p110α inhibitors Bioorg. Med. Chem. 14 2006 6847 6858
19. M.R. Prasad, and D.P. Kishore Multistep, microwave assisted, solvent free synthesis and antibacterial activity of 6-substituted-2,3,4-trihydropyrimido[1, 2-c]9,10,11,12-tetrahydrobenzo[b]thieno[3,2-e]pyrimidines Chem. Pharm. Bull. 55 2007 776 779
20. A.E. Kassab, and E.M. Gedawy Synthesis and anticancer activity of novel 2-pyridyl hexahyrocyclooctathieno[2,3-d]pyrimidine derivatives Eur. J. Med. Chem. 63 2013 224 230
21. M. Sridhar, R.M. Rao, N.H.K. Baba, and R.M. Kumbhare Microwave- accelerated Gewald reaction: synthesis of 2-aminothiophenes Tetrahedron Lett. 48 2007 3171 3172
22. R. Rajagopal, T.M. Jyothi, T. Daniel, K.V. Srinivasan, and B.S. Rao Calcined Mg-Al hydrotalcite as a heterogeneous base catalyst for Gewald aminothiophene synthesis Synth. Commun. 31 2001 3113 3117
23. T. Wang, X.G. Huang, and J. Liu et al. An efficient one-pot synthesis of substituted 2-aminothiophenes via three-component Gewald reaction catalyzed by l-proline Synlett 2010 1351 1354
24. D.D. Zhao, L. Li, F. Xu, Q. Wu, and X.F. Lin Bovine serum albumin-catalyzed one-pot synthesis of 2-aminothiophenes via Gewald reaction J. Mol. Catal. B-Enzym. 95 2013 29 35
25. R. Tayebee, F. Javadi, and G. Argi Easy single-step preparation of ZnO nano-particles by sedimentation method and studying their catalytic performance in the synthesis of 2-aminothiophenes via Gewald reaction J. Mol. Catal. A-Chem. 368-369 2013 16 23
26. E. Rezaei-Seresht, R. Tayebee, and M. Yasemi KG-60-piperazine as a new heterogeneous catalyst for Gewald three-component reaction Synth. Commun. 43 2013 1859 1864
27. P. Malherbe, R. Masciadri, R.D. Norcross, H. Ratni, A.W. Thomas, Thieno-pyridine derivatives as allosteric enhancers of the GABAB receptors, US2006135552 (2006).
28. G.M. Sheldrick A short history of SHELX Acta Cryst. A64 2008 112 122
29. M.C. Alley, D.A. Scudiero, and A. Monks et al. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay Cancer Res. 48 1988 589 601