A regioselective synthesis of some new pyrazol-1′-ylpyrazolo[1,5-a] pyrimidines in aqueous medium and their evaluation as antimicrobial agents

European Journal of Medicinal Chemistry

Volumn 46, Issue 7, 2011, Pages 3038-3046

  Aggarwal, Ranjana ^a   Sumran, Garima ^a,b   Garg, Neelam ^a   Aggarwal, Ashok ^a  

^a KURUKSHETRA UNIVERSITY   (India)

^b Technology Education and Research Integrated Institutions   (India)

Author keywords

Antibacterial activity; Antifungal activity; Aquoeus medium synthesis; Pyrazol 1 ylpyrazolo 1,5 a pyrimidines; Regioisoselective synthesis

Indexed keywords

1,3 DIKETONE; 2 (3' METHYL 5' (4'' BROMOPHENYL)PYRAZOL 1' YL) 5 METHYL 7 (4'' BROMOPHENYL)PYRAZOLO[1,5 A]PYRIMIDINE; 2 (3' METHYL 5' (4'' CHLOROPHENYL)PYRAZOL 1' YL) 5 METHYL 7 (4'' CHLOROPHENYL)PYRAZOLO[1,5 A]PYRIMIDINE; 2 (3' METHYL 5' (4'' METHOXYPHENYL)PYRAZOL 1' YL) 5 METHYL 7 (4'' METHOXYPHENYL)PYRAZOLO[1,5 A]PYRIMIDINE; 2 (3' METHYL 5' (4'' METHYLPHENYL)PYRAZOL 1' YL) 5 METHYL 7 (4'' METHYLPHENYL)PYRAZOLO[1,5 A]PYRIMIDINE; 2 (3' METHYL 5' (THIEN 2'' YL)PYRAZOL 1' YL) 5 METHYL 7 (THIEN 2'' YL)PYRAZOLO[1,5 A]PYRIMIDINE; 2 (3' METHYL 5' PHENYLPYRAZOL 1' YL) 5 METHYL 7 PHENYLPYRAZOLO[1,5 A]PYRIMIDINE; 2 (3' METHYL 5',6' DIHYDRO 4H CYCLOPENTA[D]PYRAZOL 1' YL) 5 METHYL 7,8 DIHYDRO 6H CYCLOPENTA[G]PYRAZOLO[1,5 A]PYRIMIDINE; 3 METHYL 5 (2 THIENYL) 1H PYRAZOLE; 3 METHYL 5 (4 BROMOPHENYL) 1H PYRAZOLE; 3 METHYL 5 (4 CHLOROPHENYL) 1H PYRAZOLE; 3 METHYL 5 (4 METHOXYPHENYL) 1H PYRAZOLE; 3 METHYL 5 (4 METHYLPHENYL) 1H PYRAZOLE; ANTIINFECTIVE AGENT; GENTAMICIN; LINEZOLID; PYRAZOL 1' YLPYRAZOLO[1,5 A]PYRIMIDINE; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; ACETAMIDE DERIVATIVE; ANTIFUNGAL AGENT; OXAZOLIDINONE DERIVATIVE;

AGAR DIFFUSION; ALTERNARIA ALTERNATA; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS TERREUS; BACILLUS CEREUS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; FUSARIUM OXYSPORUM; HYPHOMYCETES; INFRARED SPECTROMETRY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; ALTERNARIA; ASPERGILLUS; DRUG EFFECTS; FUSARIUM; GROWTH, DEVELOPMENT AND AGING; MICROBIAL SENSITIVITY TEST; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACETAMIDES; ALTERNARIA; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ASPERGILLUS; BACILLUS CEREUS; ESCHERICHIA COLI; FUSARIUM; GENTAMICINS; HELMINTHOSPORIUM; MICROBIAL SENSITIVITY TESTS; OXAZOLIDINONES; PSEUDOMONAS AERUGINOSA; PYRAZOLES; PYRIMIDINES; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79957518130     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.04.041     Document Type: Article

References (63)

1. Jo A. Alexander, G.P. Wheeler, D.D. Hill, and H.P. Morris Biochem. Pharmacol. 15 1966 881 889
2. R.A. Earl, R.J. Pugmire, G.R. Revankar, and L.B. Townsend J. Org. Chem. 40 1975 1822 1828
3. T. Novinson, R. Hanson, M.K. Dimmitt, L.N. Simon, R.K. Robins, and D.E. O'Brien J. Med. Chem. 17 1974 645 648
4. C. Almansa, A.F. de Arriba, F.L. Cavalcanti, L.A. Gomez, A. Miralles, M. Merlos, J. Garcia-Rafanell, and J. Forn J. Med. Chem. 44 2001 350 361
5. G.J. Reddy, S. Sailaja, K.S. Rao, P. Reddanna, and D.B. Reddy Indian J. Chem. 44B 2005 204 206
6. K. Paruch, M.P. Dwyer, C. Alvarez, C. Brown, T.-Y. Chan, R.J. Doll, K. Keertikar, C. Knutson, B. McKittrick, J. Rivera, R. Rossman, G. Tucker, T.O. Fischmann, A. Hruza, V. Madison, A.A. Nomeir, Y. Wang, E. Lees, D. Parry, N. Sgambellone, W. Seghezzi, L. Schultz, F. Shanahan, D. Wiswell, X. Xu, Q. Zhou, R.A. James, V.M. Paradkar, H. Park, L.R. Rokosz, T.M. Stauffer, and T.J. Guzi Bioorg. Med. Chem. Lett. 17 2007 6220 6223
7. H. Mukaiyama, T. Nishimura, S. Kobayashi, Y. Komatsu, S. Kikuchi, T. Ozawa, N. Kamada, and H. Ohnota Bioorg. Med. Chem. 16 2008 909 921
8. D.R. Compton, S. Sheng, K.E. Carlson, N.A. Rebacz, I.Y. Lee, B.S. Katzenellenbogen, and J.A. Katzenellenbogen J. Med. Chem. 47 2004 5872 5893
9. A. Lippa, P. Czobor, J. Stark, B. Beer, E. Kostakis, M. Gravielle, S. Bandyopadhyay, S.J. Russek, T.T. Gibbs, D.H. Farb, and P. Skolnick Proc. Natl. Acad. Sci. U.S.A. 102 2005 7380 7385
10. F. Wegner, W. Deuther-Conrad, M. Scheunemann, P. Brust, S. Fischer, A. Hiller, M. Diekers, K. Strecker, K. Wohlfarth, C. Allagaier, J. Steinbach, and A. Hoepping Eur. J. Pharmacol. 580 2008 1 11
11. S. Selleri, P. Gratteri, C. Costagli, C. Bonaccini, A. Costanzo, F. Melani, G. Guerrini, G. Ciciani, B. Costa, F. Spinetti, C. Martini, and F. Bruni Bioorg. Med. Chem. 13 2005 4821 4834
12. C. Chen, K.M. Wilcoxen, C.Q. Huang, Y.-F. Xie, J.R. McCarthy, T.R. Webb, Y.-F. Zhu, J. Saunders, X.-J. Liu, T.-K. Chen, H. Bozigian, and D.E. Grigoriadis J. Med. Chem. 47 2004 4787 4798
13. R.E. Petroski, J.E. Pomeroy, R. Das, H. Bowman, W. Yang, A.P. Chen, and A.C. Foster J. Pharmacol. Exp. Ther. 317 2006 369 377
14. F. Korodi, E. Feher, E. Magyar, Process for the Production of N-3-(3-Cyanopyrazolo-[1,5-a]Pyrimidin-7-yl)-Phenyl]-N-Ethylacetamide (Zaleplon), WO Patent 02/100828, December 19, 2002;
15. Y. Dundar, S. Dodd, J. Strobl, A. Boland, R. Dickson, and T. Walley Hum. Psychopharmacol. 19 2004 305 322
16. J. Li, Y.F. Zhao, X.L. Zhao, X.Y. Yuan, and P. Gong Arch. Pharm. 339 2006 593 597
17. O.M. Ahmed, M.A. Mohamed, R.R. Ahmed, and S.A. Ahmed Eur. J. Med. Chem. 44 2009 3519 3523
18. Y.L. Chen, J.P. Patent 2000502723;
19. Chem. Abstr. 17 1998 204905
20. S. Selleri, F. Bruni, C. Costagli, A. Costanzo, G. Guerrini, G. Ciciani, P. Gratteri, F. Besnard, B. Costa, M. Montali, C. Martini, J. Fohlin, G.D. Siena, and P.M. Aiello J. Med. Chem. 48 2005 6756 6760
21. P. Popik, E. Kostakis, M. Krawczyk, G. Nowak, B. Szewczyk, P. Krieter, Z. Chen, S.J. Russek, T.T. Gibbs, D.H. Farb, P. Skolnick, A.S. Lippa, and A.S. Basile J. Pharmacol. Exp. Ther. 319 2006 1244 1252
22. S. Bondock, W. Fadaly, and M.A. Metwally Eur. J. Med. Chem. 45 2010 3692 3701
23. M.H. Elnagdi, M.R.H. Elmoghayar, and G.E.H. Elgemeie A.R. Katritzky, Chemistry of Pyrazolopyrimidines Advances in Heterocyclic Chemistry vol. 41 1987 Academic Press Inc. New York, USA 319 376
24. J.S. Bajwa, and P.J. Sykes J. Chem. Soc., Perkin Trans. 1 1979 3085 3094
25. L.K. Gavrin, A. Lee, B.A. Provencher, W.W. Massefski, S.D. Huhn, G.M. Ciszewski, D.C. Cole, and J.C. McKew J. Org. Chem. 72 2007 1043 1046
26. E.E. Emelina, A.A. Petrov, and A.V. Firsov Russ. J. Org. Chem. 43 2007 471 473
27. E.E. Emelina, A.A. Petrov, and A.V. Firsov Russ. J. Org. Chem. 37 2001 852 858
28. N.L. Nam, I.I. Grandberg, and V.I. Sorokin Chem. Heterocycl. Compd. 38 2002 1371 1374
29. A.A. Petrov, E.E. Emelina, and S.I. Selivanov Russ. J. Org. Chem. 44 2008 263 269
30. R. Aggarwal, G. Sumran, R.M. Claramunt, D. Sanz, and J. Elguero J. Mol. Struct. 934 2009 96 102
31. D. Sanz, R.M. Claramunt, A. Saini, V. Kumar, R. Aggarwal, S.P. Singh, I. Alkorta, and J. Elguero Magn. Reson. Chem. 45 2007 513 517
32. E.J. Gray, H.N.E. Stevens, and M.F.G. Stevens J. Chem. Soc., Perkin Trans. 1 1978 885 888
33. I.L. Dalinger, I.A. Vatsadse, S.A. Shevelev, and A.V. Ivachtchenko J. Comb. Chem. 7 2005 236 245
34. R. Aggarwal, G. Sumran, R. Kumar, and S.P. Singh Arkivoc xv 2007 292 302
35. M. Begtrup, J. Elguero, R. Faure, P. Camps, C. Estopá, D. Ilavsky, A. Fruchier, C. Marzin, and J. de Mendoza Magn. Reson. Chem. 26 1988 134 151
36. S.P. Singh, S. Sehgal, and L.S. Tarar Indian J. Chem. 28B 1989 27 31
37. S. Chimichi, B. Cosimelli, F. Bruni, and S. Selleri Magn. Reson. Chem. 30 1992 1117 1121
38. S. Chimichi, B. Cosimelli, F. Bruni, and S. Selleri Can. J. Chem. 70 1992 1093 1097
39. D. Sanz, R.M. Claramunt, J. Glaser, S. Trofimenko, and J. Elguero Magn. Reson. Chem. 34 1996 843 846
40. S.P. Singh, Savita, and D. Kumar Indian J. Chem. 32B 1993 262 265
41. R. Aggarwal, V. Kumar, P. Tyagi, and S.P. Singh Bioorg. Med. Chem. 14 2006 1785 1791
42. C.J. Valduga, H.S. Braibante, and M.E.F. Braibante J. Heterocycl. Chem. 34 1997 1453 1458
43. C.J. Valduga, H.S. Braibante, and M.E.F. Braibante J. Heterocycl. Chem. 35 1998 189 192
44. J. Barluenga, L. Muniz, Ma J. Iglesias, and V. Gotor J. Chem. Soc., Perkin Trans. 1 1984 611 614
45. S.P. Singh, D. Kumar, D. Kumar, and R.P. Kapoor Indian J. Chem. 34B 1995 682 685
46. G.D. Byrkit, and G.A. Michalek Ind. Eng. Chem. 42 1950 1862 1875
47. G.J. Karabatsos, and C.E. Osborne Tetrahedron 24 1968 3361 3368 and
48. sixth ed. Dictionary of Organic Compounds vol. 6 1996 Chapman and Hall London p. 5430
49. H. Adkins, W. Kutz, and D.D. Coffman J. Am. Chem. Soc. 52 1930 3212 3221
50. L.J. Beckham, and H. Adkins J. Am. Chem. Soc. 56 1934 1119 1123 2676-2679
51. J.M. Sprague, and H. Adkins J. Am. Chem. Soc. 56 1934 2669 2675
52. A.H. Tracy, and R.C. Elderfield J. Org. Chem. 6 1941 63 69
53. J.R. Stevens, and R.H. Beutel J. Am. Chem. Soc. 65 1943 449 451
54. M.L. Scott, L.C. Norris, G.F. Heuser, and W.F. Bruce J. Am. Chem. Soc. 67 1945 157
55. G.N. Walker, and B.N. Weaver J. Org. Chem. 26 1961 4441 4455
56. Y.L. Nene, and P.N. Thapliyal Fungicides in Plant Diease Control third ed. 1993 Oxford & IBH Publishing Co. Pvt. Ltd New Delhi p. 531
57. B.S. Furniss, A.J. Hannaford, P.W.G. Smith, and A.R. Tatchell Vogel's Text Book of Practical Organic Chemistry fifth ed. 1991 Longman Group England p. 634
58. Aldrich Catalogue of Chemicals 2003
59. Z. (Jack) Chen, N. Karasek, D.C. Craig, and S.B. Colbran J. Chem. Soc., Dalton Trans. 2000 3445 3452
60. D.C. Dittmer, and R. Glassman J. Org. Chem. 35 1970 999 1004
61. C. Perez, M. Paul, and P. Bazerque An antibiotic assay by the agar well diffusion method Acta. Bio. Med. Exp. 15 1990 113 115
62. J. McFarland J. Am. Med. Assoc. 14 1907 1176 1178
63. sixth ed. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically: Approved Standards vol. 23, no. 2 2003 National Committee for Clinical Laboratory Standards Villanova, PA 1-56238-486-4 NCCLS Document M7-A6