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

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

Open Access
|Aug 2017

References

  1. 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.2008.08.071
  2. 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.2012.11.033
  3. 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.2011.07.069
  4. 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.2010.03.046
  5. 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.2013.11.021
  6. 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.2014.10.007
  7. 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.2014.02.033
  8. 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/jm800295d
  9. 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)00172-0
  10. 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.2010.05.06020691339
  11. 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-2016-002927383884
  12. 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.2009.12.05620116903
  13. 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.2008.08.07118783947
  14. 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.2014.10.02225440879
  15. 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.2013.04.083371113923735831
  16. 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.2013.03.02223583911
  17. 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.2008.12.01119111461
  18. 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.2010717763363
  19. 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.2008.07.08718678487
  20. 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.2009.05.00919464884
  21. 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.2008.09.09618930654
  22. 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.2014.08.04725147148
  23. 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.2011.08.06321925884
  24. 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.198519850918
  25. 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/82.13.11072359136
  26. 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/83.11.7572041050
  27. 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.
  28. 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.2013.7323838746
  29. 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.2004.04.010
DOI: https://doi.org/10.1515/acph-2017-0028 | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075
Language: English
Page range: 275 - 292
Accepted on: May 15, 2017
Published on: Aug 30, 2017
Published by: Croatian Pharmaceutical Society
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year
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© 2017 Hend N. Hafez, Sulaiman A. Alsalamah, Abdel-Rhman B. A. El-Gazzar, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.