Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities

1. R. V. Chambhare, B. G. Khase, A. S. Bobde and R. H. Bahekar, Synthesis and preliminary evaluation of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]carbox-amide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4-ones as antimicrobial agents, Eur. J. Med. Chem. 38 (2003) 89-100; DOI: 10.1016/S0223-5234(02)01442-3.10.1016/S0223-5234(02)01442-3Search in Google Scholar

2. B. V. Ashalatha, B. Narayana, K. K. V. Raj and N. S. Kumari, Synthesis of some new bioactive 3-amino-2-mercapto-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one derivatives, Eur. J. Med. Chem. 42 (2007) 719-728; DOI: 10.1016/j.ejmech.2006.11.007.10.1016/j.ejmech.2006.11.007Search in Google Scholar

3. Z. A. Hozien, A. A. Abdel-Wahab, K. M. Hassan, F. M. Atta and S. A. Ahmed, Synthesis of some biologically active agents derived from thieno[2,3-d]pyrimidine derivatives, Pharmazie 52 (1997) 753-758.Search in Google Scholar

4. H. N. Hafez, H. A. R. Hussein and A. B. A. El-Gazzar, Design, synthesis of substituted thieno[2,3-d] pyrimidine-2,4-dithiones and its S-glycosides analogues as potential antiviral and antibacterial agents, Eur. J. Med. Chem. 45 (2010) 4026-4034; DOI: 10.1016/j.ejmech. 2010.05.060.Search in Google Scholar

5. L. D. Jennings, S. L. Kincaid, Y. D. Wang, G. Krishna-Murthy, C. F. Beyer, J. P. Mc Ginnis, M. Miranda, C. M. Discafani and S. K. Rabindran, Parallel synthesis and biological evaluation of 5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one cytotoxic agents selective for p21-deficient cells, Bioorg. Med. Chem. Lett. 15 (2005) 4731-4735; DOI: 10.1016/j.bmcl.2005.07.072.10.1016/j.bmcl.2005.07.072Search in Google Scholar

6. Y. D. Wang, S. Johnson, D. Powell, J. P. McGinnis, M. Miranda and S. K. Rabindran, Inhibition of tumor cell proliferation by thieno[2,3-d]pyrimidin-4(1H)-one-based analogs, Bioorg. Med. Chem. Lett. 15 (2005) 3763-3766; DOI: 10.1016/j.bmcl.2005.05.127.10.1016/j.bmcl.2005.05.127Search in Google Scholar

7. 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; DOI: 10.1016/j.bmcl.2008.11.090.10.1016/j.bmcl.2008.11.090Search in Google Scholar

8. A. Angell, C. McGuigan, L. G. Sevillano, R. Snoeck, G. Andrei, E. De Clercq and J. Balzarini, Bicyclic anti-VZV nucleosides, Bioorg. Med. Chem. Lett. 14 (2004) 2397-2399; DOI: 10.1016/j.bmcl.2004.03.029.10.1016/j.bmcl.2004.03.029Search in Google Scholar

9. A. Brancale, C. McGuigan, B. Algain, P. Savy, R. Benhida, J.-L. Fourrey, G. Andrei, R. Snoeck, E. De Clercq and J. Balzarini, Bicyclic anti-VZV nucleosides: Thieno analogues retain full antiviral activity, Bioorg. Med. Chem. Lett. 11 (2001) 2507-2510; DOI: 10.1016/S0960-894X(01)00471-1.10.1016/S0960-894X(01)00471-1Search in Google Scholar

10. 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.Search in Google Scholar

11. A. B. A. El-Gazzar, H. A. R. Hussein and H. N. Hafez, Synthesis and biological evaluation of thieno[2,3-d]pyrimidine derivatives for anti-inflammatory, analgesic and ulcerogenic activity, Acta Pharm. 57 (2007) 395-411; DOI: 10.2478/v10007-007-0032-6.10.2478/v10007-007-0032-618165185Search in Google Scholar

12. H. N. Hafez, O. K. Al-Duaij and A. B. A. El-Gazzar, Design synthesis and pharmacological evaluation of new nonsteroidal anti-inflammatory derived from 3-aminobenzothieno[2,3-d] pyrimidines, Int. J. Org. Chem. 3 (2013) 110-118; DOI: 10.4236/ijoc.2013.32012.10.4236/ijoc.2013.32012Search 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. C. J. Shishoo, V. S. Shirsath, I. S. Rathod, M. J. Patil and S. S. Bhargava, Design, synthesis and antihistaminic (H1) activity of some condensed 2-(substituted)-arylaminoethyl-pyrimidine-4-(3H)- ones, Arzneimittel-Forsch. 51 (2001) 221-231; DOI: 10.1055/s-0031-1300028.10.1055/s-0031-1300028Search in Google Scholar

15. M. Santagati, M. Modica, A. Santagati, F. Russo and S. Spampinato, Synthesis of amino-thienopyrimidine and thienotriazolopyrimidine derivatives as potential anti-convulsant agents, Pharmazie 51 (1996) 7-11.Search in Google Scholar

16. 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

17. D. P. Sutherlin, L. Bao, M. Berry, G. Castanedo, I. Chuckowree, J. Dotson, A. Folks, L. Friedman, R. Goldsmith, J. Gunzner, T. Heffron, J. Lesnick, C. Lewis, S. Mathieu, J. Murray, J. Nonomiya, J. Pang, N. Pegg, W. W. Prior, L. Rouge, L. Salphati, D. Sampath, Q. Tian, V. Tsui, N. C. Wan, S. Wang, B. Q. Wei, C. Wiesmann, P. Wu, B.-Y. Zhu and A. Olivero, Discovery of a potent, selective, and orally available class I phosphatidylinositol 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) kinase inhibitor (GDC-0980) for the treatment of cancer, J. Med. Chem. 54 (2011) 7579-7587; DOI: 10.1021/ jm2009327.10.1021/jm2009327Search in Google Scholar

18. M. R. Prasad, R. A. Raghuram, R. P. Shanthan, R. K. Subramanian, S. Meena and K. Madhavi, Synthesis and adenosine receptor binding studies of some novel tri-azolothieno-pyrimidines, Eur. J. Med. Chem. 43 (2008) 614-620; DOI: 10.1016/j.ejmech.2007.05.001.10.1016/j.ejmech.2007.05.001Search in Google Scholar

19. 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

20. M. I. Crespo, L. Pages, A. Vega, V. Segarra, M. Lopez, T. Domenech, M. Miralpeix, J. Beleta, H. Ryder and J. M. Palacios, Design, synthesis and biological activities of new thieno[3,2-d]pyrimidines as selective type-4 phosphodiesterase inhibitors, J. Med. Chem. 41 (1998) 4021-4035; DOI: 10.1021/ jm981012m.10.1021/jm981012m9767640Search in Google Scholar

21. M. Sugiyama, T. Sakamoto, K. Tabata and H. Fukumi, Condensed thienopyrimidine. IV. Synthesis and gastric antisecretory activity of 2,3-dihydro-5H-oxazolothienopyrimidine derivatives, Chem. Pharm. Bull. 37 (1989) 2717-2722; DOI: 10.1248/cpb.37.2717.10.1248/cpb.37.27172611931Search in Google Scholar

22. A. Gangjee, Y. Qiu, W. Li and R. L. Kisliuk, Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: Classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[ 2,3-d]pyrimidine antifolates, J. Med. Chem. 51 (2008) 5789-5797; DOI: 10.1021/jm8006933.10.1021/jm8006933389276918800768Search in Google Scholar

23. N. Pemberton, E. Chorell and F. Almqvist, Microwave-assisted synthesis and functionalization of 2-pyridones, 2-quinolones and other ring-fused 2-pyridones, Heterocycl. Chem. 1 (2006) 1-30; DOI: 10.1007/708_006.Search in Google Scholar

24. S. R. Jain and A. Kar, The antibacterial activity of some essential oils and their combination, Planta Med. 20 (1971) 118-123; DOI: 10.1055/s-0028-109967.Search in Google Scholar

25. M. J. Weinstein and G. H. Wagman, Plant-derived antibiotics in: Antibiotics Isolation, Separation and urification (Ed. L. A. Mitscher), Elsevier Scientific Publishing Company, Amsterdam 1978, p. 464.Search in Google Scholar

26. A. L. Barry and C. Thornsbery, Susceptibility testing, in: Manual of Clinical Microbiology (Ed. J. P. Lennette), American Society for Microbiology, Washington (DC) 1981, pp. 561-574.Search in Google Scholar

27. K. J. Ryan and C. G. Ray (Eds.), Sherris Medical Microbiology, 4th ed., McGraw Hill, New York 2004.Search in Google Scholar

28. K. M. Amin, M. M. Kamel, M. M. Anwar, M. Khedr and Y. M. Syam, Synthesis, biological evaluation and molecular docking of novel series of spiro [(2H,3H) quinazoline-2,10-cyclohexan]-4(1H)-one derivatives as anti-inflammatory and analgesic agents, Eur. J. Med. Chem. 45 (2010) 2117-2131; DOI: 10.1061/j.ejmech.2009.12.078.Search in Google Scholar

29. J. Zhang, D. Ren, Y. Ma, W. Wang and H. Wu, CuO nanoparticles catalyzed simple and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones under ultrasound irradiation in aqueous ethanol, Tetrahedron 70 (2014) 5274-5282; DOI: 10.1016/j.tet.2014.05.059.10.1016/j.tet.2014.05.059Search in Google Scholar