Open Access

Synthesis of thiophene and N-substituted thieno[3,2-d] pyrimidine derivatives as potent antitumor and antibacterial agents


Cite

1. H. N. Hafez and A. B. A. El-Gazzar, Design and synthesis of 3-pyrazolyl-thiophene, thieno[2,3-d] pyrimidines as new bioactive and pharmacological activities, Bioorg. Med. Chem. Lett.18 (2008) 5222–5227; DOI: 10.1016/j.bmcl.2008.08.071.10.1016/j.bmcl.2008.08.071Search in Google Scholar

2. S. Abbas, M. Hussain, S. Ali, M. Parvez, A. Raza, A. Haider and J. Iqbal, Structural, enzyme inhibition, antibacterial and DNA protection studies of organotin(IV) derivatives of thiophene-2-carboxylic acid, J. Organomet. Chem. 724 (2013) 255–261; DOI: 10.1016/j.jorganchem.2012.11.033.10.1016/j.jorganchem.2012.11.033Search in Google Scholar

3. Y. Ni. A. Gopalsamy, D. Cole, Y. Hu, R. Denny, M. Lpek, J. Liu, J. Lee, J. P. Hall, M. Luong, J. B. Telliez and L. L. Lin, Identification and SAR of a new series of thieno[3,2-d]pyrimidines as Tpl2 kinase inhibitors, Bioorg. Med. Chem. Lett. 21 (2011) 5952–5956; DOI: 10.1016/j.bmcl.2011.07.069.10.1016/j.bmcl.2011.07.069Search in Google Scholar

4. T. P. Heffron, M. Berry, G. Castanedo, C. Chang, I. Chuckowree, J. Dotson, A. Folkes, J. Gunzner, J. D. Lesnick, C. Lewis, S. Mathieu, J. Nonomiya, A. Olivero, J. Pang, D. Peterson, L. Salphati, D. Sampath, S. Sideris, D. P. Sutherlin, V. Tsui, N. C. Wan, S. Wang, S. Wong and B. Y. Zhu, Identification of GNE-477, a potent and efficacious dual PI3K/mTOR inhibitor, Bioorg. Med. Chem. Lett.20 (2010) 2408–2411; DOI: 10.1016/j.bmcl.2010.03.046.10.1016/j.bmcl.2010.03.046Search in Google Scholar

5. Q. Tan, Z. Zhang, J. Hui, Y. Zhao and L. Zhu, Synthesis and anticancer activities of thieno [3,2-d] pyrimidines as novel HDAC inhibitors, Bioorg. Med. Chem.22 (2014) 358–365; DOI: 10.1016/j.bmc.2013.11.021.10.1016/j.bmc.2013.11.021Search in Google Scholar

6. J. Kim, J. Kwon, D. Lee, S. Jo, O. Dongsik, C. Jihyun, E. Park, J. Y. Hwang, Y. Ko, I. Choi, M. K. Ju, J. Ahn, J. Kim, S.-J. Han, T.-H. Kim, J. Cechetto, J. Nam, S. Ahn, P. Sommer, M. Liuzzi and J. Lee, Serendipitous discovery of 2-((phenylsulfonyl)methyl)-thieno[3,2-d]pyrimidine derivatives as novel HIV-1 replication inhibitors, Bioorg. Med. Chem Lett. 24 (2014) 5473–5477; DOI: 10.1016/j.bmcl.2014.10.007.10.1016/j.bmcl.2014.10.007Search in Google Scholar

7. K. W. Temburnikar, S. C. Zimmermann, N. T. Kim, C. R. Ross, C. Gelbmann, C. E. Salomon, G. M. Wilson, J. Balzarini and K. L. Seley-Radtke, Antiproliferative activities of halogenated thieno[3,2-d] pyrimidines, Bioorg. Med. Chem. 22 (2014) 2113–2122; DOI: 10.1016/j.bmc.2014.02.033.10.1016/j.bmc.2014.02.033Search in Google Scholar

8. A. J. Folkes, K. Ahmadi, W. K. Alderton, S. Alix, S. J. Baker, G. Box, I. S. Chuckowree, P. A. Clarke, P. Depledge, S. A. Eccles, L. S. Friedman, A. Hayes, T. C. Hancox, A. Kugendradas, L. Lensun, P. Moore, A. G. Olivero, J. Pang, S. Patel, G. H. Pergl-Wilson, F. I. Raynaud, A. Robson, N. Saghir, L. Salphati, S. Sohal, M. H. Ultsch, M. Valenti, H. J. A. Wallweber, N. C. Wan, C. Wiesmann, P. Workman, A. Zhyvoloup, M. J. Zvelebil and S. J. Shuttleworth, The identification of 2-(1H-indazol-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (GDC-0941) as a potent, selective, orally bioavailable inhibitor of class I PI3 kinase for the treatment of cancer, J. Med. Chem. 51 (2008) 5522–5532; DOI: 10.1021/jm800295d.10.1021/jm800295dSearch in Google Scholar

9. K. A. Chakraborti, B. Gopalakrishnan, M. E. Sobhia and M. Alpeshkumar, 3D-QSAR studies on thieno [3,2-d] pyrimidines as phosphodiesterase IV inhibitors, Bioorg. Med. Chem. Lett. 13 (2003) 1403–1408; DOI: 10.1016/S0960–894X(03)00172-0.10.1016/S0960-894X(03)00172-0Search in Google Scholar

10. H. N. Hafez, H. A. R. Hussein and A. B. A. El-Gazzar, Synthesis of substituted thieno[2,3-d]pyrimidine-2,4-dithiones and their S-glycoside analogues as potential antiviral and antibacterial agents, Eur. J. Med. Chem. 45 (2010) 4026–4034; DOI: 10.1016/j.ejmech.2010.05.060.10.1016/j.ejmech.2010.05.06020691339Search in Google Scholar

11. H. N. Hafez, A. B. A. El-Gazzar and M. E. A. Zaki, Simple approach to thieno[3,2-d]-pyrimidines as new scaff olds of antimicrobial activities, Acta Pharm.66 (2016) 331–351; DOI: 10.1515/acph-2016-0029.10.1515/acph-2016-002927383884Search in Google Scholar

12. H. N. Hafez, A. B. A. El-Gazzar and G. A. M. Nawwar, Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents, Eur. J. Med. Chem. 45 (2010) 1485–1493; DOI: 10.1016/j.ejmech.2009.12.056.10.1016/j.ejmech.2009.12.05620116903Search in Google Scholar

13. H. N. Hafez and A. B. A. El-Gazzar, Design and synthesis of 3-pyrazolyl-thiophene, thieno[2,3-d] pyrimidines as new bioactive and pharmacological activity, Bioorg. Med. Chem. Lett. 18 (2008) 5222–5227; DOI: 10.1016/j.bmcl.2008.08.071.10.1016/j.bmcl.2008.08.07118783947Search in Google Scholar

14. Z. Liu, S. Wu, Y. Wang, R. Li, J. Wang, L. Wang, Y. Zhao and P. Gong, Design, synthesis and biological evaluation of novel thieno[3,2-d] pyrimidine derivatives possessing diaryl semicarbazone scaff olds as potent antitumor agents, Eur. J. Med. Chem. 87 (2014) 782–793; DOI: 10.1016/j.ejmech.2014.10.022.10.1016/j.ejmech.2014.10.02225440879Search in Google Scholar

15. M. E. Welker and G. R. Kulik, Synthesis of PI3K/Akt/mTOR signaling pathway inhibitors, Bioorg. Med. Chem.21 (2013) 4063–4091; DOI: 10.1016/j.bmc.2013.04.083.10.1016/j.bmc.2013.04.083371113923735831Search in Google Scholar

16. E. Perspicace, V. Jouan-Hureaux, R. Ragno, F. Ballante, S. Sartini, C. La Motta, F. Da Settimo, B. Chen, G. Kirsch, S. Schneider, B. Faivre and S. Hesse, Design, synthesis and biological evaluation of new classes of thieno[3,2-d]pyrimidinone and thieno[1,2,3]triazine as inhibitor of vascular endothelial growth factor receptor-2 (VEGFR-2), Eur. J. Med. Chem. 63 (2013) 765–781; DOI: 10.1016/j.ejmech.2013.03.022.10.1016/j.ejmech.2013.03.02223583911Search in Google Scholar

17. T. R. Rheault, T. R. Caferro, S. H. Dickerson, K. H. Donaldson, M. D. Gaul, A. S. Goetz, R. J. Mullin, O. B. McDonald, K. G. Petrov, D. W. Rusnak, L. M. Shewchuk, G. M. Spehar, A. T. Truesdale, D. E. Vanderwall, E. R. Wood and D. E. Uehling, Thienopyrimidine-based dual EGFR/ErbB-2 inhibitors, Bioorg. Med. Chem. Lett.19 (2009) 817–820; DOI: 10.1016/j.bmcl.2008.12.011.10.1016/j.bmcl.2008.12.01119111461Search in Google Scholar

18. G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba and A. A. Genazzani, Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides and alkynes, Med. Res. Rev.28 (2008) 278–308; DOI: 10.1002/med.20107.10.1002/med.2010717763363Search in Google Scholar

19. J. A. Demaray, J. E. Thuener, M. N. Dawson and S. Sucheck, Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity, J. Bioorg. Med. Chem. Lett.18 (2008) 4868–4871; DOI: 10.1016/j.bmcl.2008.07.087.10.1016/j.bmcl.2008.07.08718678487Search in Google Scholar

20. J. Wu, N. Green, R. Hotchandani, Y. Hu, J. Condon, A. Huang, N. Kaila, H. Q. Li, S. Guler, W. Li, S. Y. Tam, Q. Wang, J. Pelker, S. Marusic, S. Hsu, J. P. Hall, J. B. Telliez, J. Cui and L. L. Lin, Selective inhibitors of tumor progression loci-2 (Tpl2) kinase with potent inhibition of TNF-a production in human whole blood, Bioorg. Med. Chem. Lett.19 (2009) 3485–3488; DOI: 10.1016/j.bmcl.2009.05.009.10.1016/j.bmcl.2009.05.00919464884Search in Google Scholar

21. C. Gill, G. Jadhav, M. Shaikh, R. Kale, A. Ghawalkar, D. Nagargoje and M. Shiradkar, Clubbed[1,2,3] triazoles by fluorine benzimidazole: A novel approach to H37Rv inhibitors as a potential treatment for tuberculosis, Bioorg. Med. Chem. Lett.18 (2008) 6244–6247; DOI: 10.1016/j.bmcl.2008.09.096.10.1016/j.bmcl.2008.09.09618930654Search in Google Scholar

22. M. M. Kamel and N. Y. Megally Abdo, Synthesis of novel 1,2,4-triazoles, triazolothiadiazines and triazolothiadiazoles as potential anticancer agents, Eur. J. Med. Chem. 86 (2014) 75–80; DOI: 10.1016/j.ejmech.2014.08.047.10.1016/j.ejmech.2014.08.04725147148Search in Google Scholar

23. Y. P. Hou, J. Sun, Z. H. Pang, P. C. Lv, D. D. Li, L. Yan, H. J. Zhang, E. X. Zheng, J. Zhao and H. L. Zhu, Synthesis and antitumor activity of 1,2,4-triazoles having 1,4-benzodioxan fragment as a novel class of potent methionine aminopeptidase type II inhibitors, Bioorg. Med. Chem.19 (2011) 5948–5954; DOI: 10.1016/j.bmc.2011.08.063.10.1016/j.bmc.2011.08.06321925884Search in Google Scholar

24. H. Wamhoff, M. Ertas and S. M. S. Atta, Notizen heterocyclic β-enamino esters, 39. Synthesis of 1H-pyrazolo[3,4-d]pyrimidines, Liebigs Ann. Chem.9 (1985) 1910–1916; DOI: 10.1002/jlac.198519850918.10.1002/jlac.198519850918Search in Google Scholar

25. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenny and M. R. Boyd, New colorimetric cytotoxicity assay for anti-cancer drug screening, J. Natl. Cancer Inst. 82 (1990) 1107–1112; DOI: 10.1093/jnci/82.13.1107.10.1093/jnci/82.13.11072359136Search in Google Scholar

26. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paul, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo and J. M. Boyd, Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst. 83 (1991) 757–766; DOI: 10.1093/jnci/83.11.757.10.1093/jnci/83.11.7572041050Search in Google Scholar

27. M. J. Weinstein and G. H. Wagman, Plant-derived Antibiotics, in Antibiotics Isolation, Separation and Purification (Ed. L. A. Mitscher), Elsevier, Amsterdam 1978, p. 464.Search in Google Scholar

28. H. Naeimi, Z. S. Nazifi, S. M. Amininezhad and M. Amouheidari, Synthesis, characterization and in vitro antimicrobial activity of some new Schiff bases and their complexes, J. Antibiot. 66 (2013) 687–689; DOI: 10.1038/ja.2013.73.10.1038/ja.2013.7323838746Search in Google Scholar

29. P. G. Baraldi, H. El-Kashef, A. Farghaly, P. Vanelle and F. Fruttarolo, Synthesis of new pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines and related heterocycles, Tetrahedron60 (2004) 5093–5104; DOI: 10.1016/j.tet.2004.04.010.10.1016/j.tet.2004.04.010Search in Google Scholar

eISSN:
1846-9558
Language:
English
Publication timeframe:
4 times per year
Journal Subjects:
Pharmacy, other