Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 5056-5063

  Kamdar, Nimesh R ^a   Haveliwala, Dhaval D ^a   Mistry, Prashant T ^a   Patel, Saurabh K ^a  

^a VEER NARMAD SOUTH GUJARAT UNIVERSITY   (India)

Author keywords

Antimicrobial activity; Antitubercular activity; Pyranopyrimidine; Pyrimidine thiones; Pyrimidone

Indexed keywords

11 AMINO 12 (4 METHOXYPHENYL) 8,12 DIHYDRO 9H BENZO[5,6]CHROMENO[2,3 D]PYRIMIDINE 9 ONE; 11 AMINO 12 (4 METHOXYPHENYL) 8,12 DIHYDRO 9H BENZO[5,6]CHROMENO[2,3 D]PYRIMIDINE 9 THIONE; 12 (4 METHOXYPHENYL) 10,12 DIHYDRO 11H BENZO[5,6]CHROMENO[2,3 D]PYRIMIDINE 11 ONE; 12 (4 METHOXYPHENYL) 8,12 DIHYDRO 9H BENZO[5,6] CHROMENO[2,3 D]PYRIMIDINE 9,11(10H) DITHIONE; 2 AMINO 4 (4 METHOXYPHENYL) 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (4 METHOXYPHENYL) 4H CHROMENE 3 CARBONITRILE; 2 AMINO 4 (4 METHOXYPHENYL) 4H PYRANO[3,2 H]QUINOLINE 3 CARBONITRILE; 2 AMINO 7 HYDROXY 4 (4 METHOXYPHENYL) 4H CHROMENE 3 CARBONITRILE; 3 AMINO 1 (4 METHOXYPHENYL) 1H BENZO[F]CHROMENE 2 CARBONITRILE; 4 AMINO 5 (4 METHOXYPHENYL) 1,5 DIHYDRO 2H CHROMENO[2,3 D]PYRIMIDINE 2 ONE; 4 AMINO 5 (4 METHOXYPHENYL) 1H CHROMENO[2,3 D]PYRIMIDINE 2(5H) THIONE; 4 AMINO 8 HYDROXY 5 (4 METHOXYPHENYL) 1,5 DIHYDRO 2H CHROMENO[2,3 D]PYRIMIDINE 2 ONE; 4 AMINO 8 HYDROXY 5 (4 METHOXYPHENYL) 1,5 DIHYDRO 2H CHROMENO[2,3 D]PYRIMIDINE 2 THIONE; 5 (4 METHOXYPHENYL) 1,5 DIHYDRO 2H CHROMENO[2,3 D] PYRIMIDINE 2,4(3H) DITHIONE; 5 [4 METHOXYPHENYL] 3,5 DIHYDRO 4H CHROMENO[2,3 D]PYRIMIDINE 4 ONE; 7 (4 METHOXYPHENYL) 7,9 DIHYDRO 8H BENZO[7,8]CHROMEN[2,3 D]PYRIMIDINE 8 ONE; 7 (4 METHOXYPHENYL) 7,9 DIHYDRO 8H PYRIMIDO[5',4':5,6]PYRANO[3,2 H]QUINOLINE 8 ONE; 7 (4 METHOXYPHENYL) 7H PYRIMIDO[5',4':5,6]PYRANO[3,2 H]QUINOLINE 8,10(9H,11H) DITHIONE; 7(4 METHOXYPHENYL) 7H BENZO[7, 8]CHROMENO[2,3 D] PYRIMIDINE 8,10(9H,11H) DITHIONE; 8 AMINO 7 (4 METHOXYPHENYL) 7,11 DIHYDRO 10H BENZO[7,8]CHROMENO[2,3 D]PYRIMIDINE 10 ONE; 8 AMINO 7 (4 METHOXYPHENYL) 7,11 DIHYDRO 10H BENZO[7,8]CHROMENO[2,3 D]PYRIMIDINE 10 THIONE; 8 AMINO 7 (4 METHOXYPHENYL) 7,11 DIHYDRO 10H PYRIMIDO[5',4':5,6]PYRANO[3,2 H]QUINOLINE 10 ONE; 8 AMINO 7 (4 METHOXYPHENYL) 7,11 DIHYDRO 10H PYRIMIDO[5',4':5,6]PYRANO[3,2 H]QUINOLINE 10 THIONE; 8 HYDROXY 5 (4 METHOXYPHENYL) 1,5 DIHYDRO 2H CHROMENO[2,3 D]PYRIMIDINE 2,4(3H) DITHIONE; 8 HYDROXY 5 (4 METHOXYPHENYL) 3,5 DIHYDRO 4H CHROMENO[2,3 D]PYRIMIDINE 4 ONE; PYRIMIDINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACTERIAL STRAIN; DRUG DESIGN; DRUG SYNTHESIS; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; INFRARED SPECTROSCOPY; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PYOGENES;

ANTI-INFECTIVE AGENTS; ASPERGILLUS NIGER; BACTERIA; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; PYRIMIDINES;

EID: 77957854053     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.08.014     Document Type: Article

References (30)

1. E. Bogatcheva, C. Hanrahan, B. Nikonenko, R. Samala, P. Chen, J. Gearhart, F. Barbosa, L. Einck, C. Nacy, and M. Protopopova J. Med. Chem. 49 2006 3045 3048
2. Tuberculosis Facts 2006 WHO
3. M.S. Ponnurengam, K.G. Sethu, and M. Doble Chem. Pharm. Bull. 55 2007 44 49
4. S.C. Ren, F.Y. Sheau, M.L. Chih, G. Amooru, T.K. Damu, C.P. Cheng, F.B. Kenneth, L.K. Hsiung, and W.T. Shung Bioorg. Med. Chem. 17 2009 6137 6143
5. A.V. Karnik, A.M. Kulkarni, N.J. Malviya, B.R. Mourya, and B.L. Jadhav Eur. J. Med. Chem. 43 2008 2615 2617
6. K.J. Hwan, K.H. Eun, J.J. Kyung, K. Hwajung, C. Jungsook, and L. Heesoon Arch. Pharm. Res. 29 2006 728 734
7. C. Fakher, M. Mehdi, B.M. Hedi, C. Leila, and S. Mansour Eur. J. Med. Chem. 42 2007 715 718
8. C.Y. Cheng, H. Chiu, M.J. Chang, Y.C. Lin, M.C. Tsai, and H.C. Yu Bioorg. Med. Chem. Lett. 8 1998 463 468
9. O.A. Abdou, H.E. Ahmed, A.A. Sayed, and H.Z. Yasser J. Sulf. Chem. 26 2005 405 410
10. M.B. Deshmukh, S.M. Salunkhe, D.R. Patil, and P.V. Anbhule Eur. J. Med. Chem. 44 2009 2651 2654
11. G. Cecile, D. Douguet, V. Huteau, M. Gilles, M.L. Helene, and P. Sylvie Bioorg. Med. Chem. 16 2008 6075 6085
12. R. Lin, G. Sigmond, P.J. Johnson, S.K. Connolly, E. Wetter, T.V. Binnun, W.V. Hughes, N.B. Murray, S.J. Pandey, M.M. Mazza, A.R. Adams, F. Pesquera, and A.M. Steven Bioorg. Med. Chem. Lett. 19 2009 2333 2337
13. E.P. Falcao, S. da, S.J. Melo, R.M. Srivastava, M.T. Catanho, and S.C. Nascimento Eur. J. Med. Chem. 41 2006 276 282
14. Q. Chen, X. Zhu, L. Jiang, L.M. Yang, and G. Fu Eur. J. Med. Chem. 43 2008 595 603
15. A. Agarwal, R. Ashutosh, N. Goyal, M.S. Chauhana, and S. Gupta Bioorg. Med. Chem. 13 2005 6678 6684
16. O. Bruno, S. Schenone, A. Ranise, F. Bondavalli, W. Filippelli, G. Falcone, G. Motola, and F. Mazzeo Il Farmaco 54 1999 95 100
17. A. Agarwal, Ramesh, Ashutosh, N. Goyal, P.M.S. Chauhana, and S. Gupta Bioorg. Med. Chem. 13 2005 6678 6684
18. J.J.V. Eynde, N. Hecq, O. Kataeva, and C.O. Kappe Tetrahedron 57 2001 1785 1791
19. S. Buscemi, A. Pace, A.P. Piccionello, N. Vivona, and M. Pani Tetrahedron 62 2006 1158 1164
20. A. Luke, P. Soizic, H. Valerie, S. Brigitte, M. Sylvie, K. Michel, T.C. Stewart, T. Francois, and L.J. Yves Bioorg. Med. Chem. 16 2008 8264 8272
21. G. Cecile, D. Dominique, H. Valerie, M. Gilles, M. Helene, and P. Sylvie Bioorg. Med. Chem. 16 2008 6075 6085
22. M.T. Chhabria, and M.H. Jani Eur. J. Med. Chem. 44 2009 3837 3844
23. M. Wenyan, L. Guihong, T. Wang, and H. He J. Fluo, Chem. 129 2008 519 523
24. J.D. Akbari, P.K. Kachhadia, S.D. Tala, A.H. Bapodra, M.F. Dhaduk, H.S. Joshi, K.B. Mehta, and S.J. Pathak Phosphorus Sulfur Silicon 183 2008 1911 1922
25. A. Davoodnia, H. Behmadi, A. Zare Bidaki, M. Bakavoli, and N. Tavakoli Hoseini Chin. Chem. Lett. 18 2007 1163 1165
26. M.S. Behalo Phosphorus Sulfur Silicon 184 2009 206 219
27. P.G. Baraldi, H. El-Kashef, A.R. Farghaly, P. Vanelle, and F. Fruttarolo Tetrahedron 60 2004 5093 5104
28. B. Roberto, B. Giovanna, L.C. Maria, M. Raimondo, M. Alessandro, R. Paolo, and S. Giovanni Tetrahedron 57 2001 1395 1398
29. J.G. Collee, J.P. Duguid, A.G. Fraser, B.P. Marmion, Practical Medical Microbiology 13th ed. 1989 Mackie, Cartney, Mc 600 649
30. S. Siddiqi Clinical Microbiology Handbook 1992 ASM Press Washington D.C.