Thieno[2,3-d]pyrimidinedione derivatives as antibacterial agents

European Journal of Medicinal Chemistry

Volumn 51, Issue , 2012, Pages 145-153

  Dewal, Mahender B ^a   Wani, Amit S ^a   Vidaillac, Celine ^a,b   Oupický, David ^a   Rybak, Michael J ^a   Firestine, Steven M ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b NANCY UNIVERSITÉ   (France)

Author keywords

Antibacterial; Antibiotic resistant bacteria; Heterocycle synthesis; MRSA; Thieno 2,3 d pyrimidinediones

Indexed keywords

ANTIBIOTIC AGENT; PYRIMIDINE DERIVATIVE; THIENO[2,3 D]PYRIMIDINEDIONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; NONHUMAN; REACTION ANALYSIS;

ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIA; HEMOLYSIS; MICE; NIH 3T3 CELLS; PYRIMIDINONES; SHEEP;

EID: 84860279600     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.02.035     Document Type: Article

References (32)

1. P.C. Appelbaum MRSA - the tip of the iceberg Clinical Microbiology and Infection 12 2006 3 10 (Pubitemid 43355765)
2. W.R. Bishai, N. Zetola, J.S. Francis, and E.L. Nuermberger Community-acquired meticillin-resistant Staphylococcus aureus: an emerging threat The Lancet Infectious Diseases 5 2005 275 286 (Pubitemid 40602247)
3. D.H. Williams, and B. Bardsley The vancomycin group of antibiotics and the fight against resistant bacteria Angewandte Chemie, International Edition 38 1999 1173 1193 (Pubitemid 29234577)
4. C. Walsh Molecular mechanisms that confer antibacterial drug resistance Nature 406 2000 775 781
5. 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 European Journal of Medicinal Chemistry 42 2007 719 728 (Pubitemid 46722735)
6. A.E. Rashad, A.H. Shamroukh, R.E. Abdel-Megeid, and W.A. El-Sayed Synthesis, reactions, and antimicrobial evaluation of some polycondensed thienopyrimidine derivatives Synthetic Communications 40 2010 1149 1160
7. R.V. Chambhare, B.G. Khadse, 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]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H- thieno[2,3-d]pyrimidin-4-ones as antimicrobial agents European Journal of Medicinal Chemistry 38 2003 89 100 (Pubitemid 36197857)
8. M.A. Elsherbeny, M.B. Elashmawy, H.I. Elsubbagh, A.A. Elemam, and F.A. Badria Synthesis, antimicrobial and antiviral evaluation of certain thienopyrimidine derivatives European Journal of Medicinal Chemistry 30 1995 445 449
9. A.E. Rashad, and M.A. Ali Synthesis and antiviral screening of some thieno 2,3-d pyrimidine nucleosides Nucleosides Nucleotides & Nucleic Acids 25 2006 17 28
10. V. Alagarsamy, S. Meena, K.V. Ramseshu, V.R. Solomon, K. Thirumurugan, K. Dhanabal, and M. Murugan Synthesis, analgesic, anti-inflammatory, ulcerogenic index and antibacterial activities of novel 2-methylthio-3-substituted-5,6,7,8- tetrahydrobenzo(b)thieno 2,3-d pyrimidin-4(3H)-ones European Journal of Medicinal Chemistry 41 2006 1293 1300
11. J.F. Deng, L. Peng, G.C. Zhang, X.B. Lan, C.F. Li, F.X. Chen, Y.Y. Zhou, Z.X. Lin, L. Chen, R.K. Dai, H.J. Xu, L. Yang, X.Q. Zhang, and W.H. Hu The highly potent and selective dipeptidyl peptidase IV inhibitors bearing a thienopyrimidine scaffold effectively treat type 2 diabetes European Journal of Medicinal Chemistry 46 2011 71 76
12. T. Horiuchi, M. Nagata, M. KitagawaB, 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 Bioorganic & Medicinal Chemistry 17 2009 7850 7860
13. A.A. Aly, A.B. Brown, M. Ramadan, A.M. Gamal-Eldeen, M. Abdel-Aziz, G.E.-D.A.A. Abuo-Rahma, and M.F. Radwan Thieno 2,3-d pyrimidines in the synthesis of antitumor and antioxidant agents Archiv Der Pharmazie 343 2010 301 309
14. K.M. Al-Taisan, H.M.A. Al-Hazimi, and S.S. Al-Shihry Synthesis, characterization and biological studies of some novel thieno 2,3-d pyrimidines Molecules 15 2010 3932 3957
15. A.E. Rashad, A.H. Shamroukh, R.E. Abdel-Megeid, A. Mostafa, R. El-Shesheny, A. Kandeil, M.A. Ali, and K. Banert Synthesis and screening of some novel fused thiophene and thienopyrimidine derivatives for anti-avian influenza virus (H5N1) activity European Journal of Medicinal Chemistry 45 2010 5251 5257
16. V.D. Patil, D.S. Wise, and L.B. Townsend The synthesis of thieno 2,3-D pyrimidine nucleosides related to the naturally-occurring nucleosides cytidine and uridine Journal of the Chemical Society-Perkin Transactions 1 1980 1853 1858
17. R.W. Sabnis The Gewald synthesis Sulfur Reports 16 1994 1 17
18. R.W. Sabnis, D.W. Rangnekar, and N.D. Sonawane 2-Aminothiophenes by the Gewald reaction Journal of Heterocyclic Chemistry 36 1999 333 345 (Pubitemid 29220939)
19. T. Bhattacharyya, A. Sundin, and U.J. Nilsson Synthesis of chiral, amphiphilic, and water-soluble macrocycles via urea formation Tetrahedron 59 2003 7921 7928 (Pubitemid 37130316)
20. G. Cimino, M. Gavagnin, G. Sodano, A. Spinella, G. Strazzullo, F.J. Schmitz, and G. Yalamanchili Revised structure of bursatellin The Journal of Organic Chemistry 52 1987 2301 2303
21. E.J. Corey, K.C. Nicolaou, R.D. Balanson, and Y. Machida Useful method for the conversion of azides to amines Synthesis 1975 590 591
22. M. Matsuno, A. Nagatsu, Y. Ogihara, and H. Mizukami Synthesis of 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactic acid, an important intermediate of rosmarinic acid biosynthesis Chemical & Pharmaceutical Bulletin 49 2001 1644 1646 (Pubitemid 33126598)
23. A. Servais, M. Azzouz, D. Lopes, C. Courillon, and M. Malacria Radical cyclization of N-acylcyanamides: total synthesis of luotonin A Angewandte Chemie, International Edition 46 2007 576 579 (Pubitemid 46159201)
24. S. Tsuchida, A. Kaneshige, T. Ogata, H. Baba, Y. Yamamoto, and K. Tomioka Consecutive cyclization of allylaminoalkene by intramolecular aminolithiation-carbolithiation Organic Letters 10 2008 3635 3638
25. S.D. Young, L.S. Payne, W.J. Thompson, N. Gaffin, T.A. Lyle, S.F. Britcher, S.L. Graham, T.H. Schultz, A.A. Deana, P.L. Darke, J. Zugay, W.A. Schleif, J.C. Quintero, E.A. Emini, P.S. Anderson, and J.R. Huff Hiv-1 protease inhibitors based on hydroxyethylene dipeptide isosteres - an investigation into the role of the P1' side-chain on structure activity The Journal of Medicinal Chemistry 35 1992 1702 1709
26. H. Zhao, M.Z. Cai, and C.Y. Peng Stereoselective synthesis of (E)-cinnamonitriles via Heck arylation of acrylonitrile and aryl iodides in water Synthetic Communications 32 2002 3419 3423 (Pubitemid 35247348)
27. J. Dumas, R. Sibley, and J. Wood Application: WO Preparation of Thienopyrimidines as Inhibitors of Prolylpeptidase, Inducers of Apoptosis and Cancer Treatment Agents 2003 Bayer Corporation USA 50
28. A.R. Ekkati, V. Mandiyan, K.P. Ravindranathan, J.H. Bae, J. Schlessinger, and W.L. Jorgensen Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors Tetrahedron Letters 52 2011 2228 2231
29. W.J. McClellan, Y.J. Dai, C. Abad-Zapatero, D.H. Albert, J.J. Bouska, K.B. Glaser, T.J. Magoc, P.A. Marcotte, D.J. Osterling, K.D. Stewart, S.K. Davidsen, and M.R. Michaelides Discovery of potent and selective thienopyrimidine inhibitors of Aurora kinases Bioorganic & Medicinal Chemistry Letters 21 2011 5620 5624
30. Y.K. Ni, A. Gopalsamy, D. Cole, Y.H. Hu, R. Denny, M. Ipek, 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 Bioorganic & Medicinal Chemistry Letters 21 2011 5952 5956
31. Y. Deng, X. Zhou, S. Kugel Desmoulin, J. Wu, C. Cherian, Z. Hou, L.H. Matherly, and A. Gangjee Synthesis and biological activity of a novel series of 6-Substituted thieno[2,3-d]pyrimidine antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors over the reduced folate carrier and proton-coupled folate transporter for cellular entry The Journal of Medicinal Chemistry 52 2009 2940 2951
32. Clinical Laboratory and Standard Institute Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically; Approved Standard nineth ed. 2010 CLSI Wayne, PA