Eco-friendly synthesis and biological evaluation of substituted pyrano[2,3-c]pyrazoles

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 16, 2012, Pages 5272-5278

  Mandha, Santhosh Reddy ^a   Siliveri, Sravanthi ^b   Alla, Manjula ^a   Bommena, Vittal Rao ^a   Bommineni, Madhava Reddy ^b   Balasubramanian, Sridhar ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b G Pulla Reddy College of Pharmacy   (India)

Author keywords

Anti inflammatory activity; Antibacterial activity; Cytotoxic activity; Multicomponent reactions; Non catalytic conditions

Indexed keywords

ALCOHOL; ANTIBIOTIC AGENT; ANTIINFLAMMATORY AGENT; CIPROFLOXACIN; IBUPROFEN; PACLITAXEL; PYRANO[2,3 C]PYRAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; AQUEOUS SOLUTION; ARTICLE; BACILLUS SUBTILIS; BREAST CANCER; CANCER CELL CULTURE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; GREEN CHEMISTRY; HUMAN; HUMAN CELL; IC 50; IN VIVO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; ONE POT SYNTHESIS; PAW EDEMA; PSEUDOMONAS AERUGINOSA; RAT; STAPHYLOCOCCUS AUREUS;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTI-INFLAMMATORY AGENTS; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; EDEMA; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HUMANS; MCF-7 CELLS; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; PYRAZOLES; RATS;

EID: 84864399585     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.06.055     Document Type: Article

References (48)

1. W.P. Smith, L.S. Sollis, D.P. Howes, C.P. Cherry, D.I. Starkey, and N.K. Cobley J. Med. Chem. 41 1998 787
2. K. Mazaahir, S. Shilpi, R.K. Khalilur, and S.T. Sharanjit Bioorg. Med. Chem. Lett. 15 2005 4295
3. J.L. Wang, D. Liu, Z.J. Zheng, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, and Z. Huang Proc. Natl. Acad. Sci. U.S.A. 97 2009 7124
4. M.E.A. Zaki, E.M. Morsy, and M. Abdul Heterocycl. Commun. 10 2004 97
5. M.E.A. Zaki, H.A. Saliman, O.A. Hickal, and A.E. Rashad Z. Naturforsch., C: Biosci. 61 2006 1
6. C.K. Sheng, J.H. Li, and N. Hideo J. Med. Chem. 27 1984 539
7. N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, and A.E. Surgenor Bioorg. Med. Chem. 14 2006 4792
8. H. Junek, and H. Aigner Chem. Ber. 106 1973 914
9. H. Wamhoff, E. Kroth, and K. Strauch Synthesis 11 1993 1129
10. A.V. Stachulski, N.G. Berry, A.C.L. Low, S.L. Moores, E. Row, D.C. Warhurst, I.S. Adagu, and J.F. Rossignol J. Med. Chem. 49 2006 1450
11. D.J. Ramon, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602
12. J. Zhu Eur. J. Org. Chem. 2003 1133
13. I. Ugi, A. Domling, and B. Werner J. Heterocycl. Chem. 37 2000 647
14. H. Bienayme, C. Hulme, G. Oddon, and P. Schmitt Chem. Eur. J. 6 2000 3321
15. V.S. Shinu, B. Sheeja, E. Purushothaman, and D. Bahulayan Tetrahedron Lett. 50 2009 4838
16. A. Arabanian, M. Mohammadnejad, S. Balalaie, and J.H. Gross Bioorg. Med. Chem. Lett. 19 2009 887
17. V.A. Chebanov, E.A. Muravyova, S.M. Desenko, V.I. Musatov, I.V. Knyazeva, S.V. Shishkina, O.V. Shishkin, and C.O. Kappe J. Comb. Chem. 8 2006 427
18. A. Dondoni, A. Massi, S. Sabbatini, and V. Bertolasi J. Org. Chem. 67 2002 6979
19. G. Rashinkar, and R. Salunkhe J. Mol. Catal. A: Chem. 316 2010 146
20. P. Srihari, V.K. Singh, D.C. Bhunia, and J.S. Yadav Tetrahedron Lett. 50 2009 3763
21. Y.A. Sharanin, L.G. Sharanina, and V.V. Puzanova Zh. Org. Khim. 19 1983 2609
22. H. Mecadon, M.R. Rohman, I. Kharbangar, B.M. Laloo, I. Kharkongor, M. Rajbangshi, and B. Myrboh Tetrahedron Lett. 52 2011 3228
23. H.V. Chavan, S.B. Babar, R.U. Hoval, and B.P. Bandgar Bull. Chem. Soc. 32 2011 3963
24. M.A. Hamad, D.K. Khaled, Y.A. Aisha, and H.E. Mohamed Molecules 15 2010 6619
25. K. Kanagaraj, and K. Pitchumani Tetrahedron Lett. 51 2010 3312
26. G. Vasuki, and K. Kumaravel Tetrahedron Lett. 49 2008 5636
27. A.M. Shestopalov, Y.M. Emeliyanova, A.A. Shestopalov, L.A. Rodinovskaya, Z.I. Niazimbetova, and D.H. Evans Org. Lett. 4 2002 423
28. A.S. Nagarajan, and B.S.R. Reddy Synlett 2002 2002
29. Z.K. Jaberi, and M.M.R. Shams Heterocycl. Commun. 17 2011 177
30. S. Hassan, and B. Maryam Synth. Commun. 40 2009 257
31. R.S. Balaskar, S.N. Gavade, M.S. Mane, D.V. Mane, B.B. Shingate, and M.S. Shingare Chin. Chem. Lett. 25 2010 1175
32. M.M. Heravi, A. Ghods, F. Derikvand, K. Bakhtiari, and F.F. Bamoharram J. Iranian Chem. Soc. 7 2010 615
33. M. Shailaja, M. Anitha, A. Manjula, and B.V. Rao Indian J. Chem., Sect. B 2010 1088
34. H. Mecadon, M.R. Rohman, M. Rajbangshi, and B. Myrboh Tetrahedron Lett. 52 2011 2523
35. F.F. Abd-ElLatif, A.K.M.N. Gohar, A.M. Fahmy, and M.Z.A. Badr Bull. Chem. Soc. 59 1986 1235
36. D. Shi, J. Mou, Q. Zhuang, L. Niu, N. Wu, and X. Wang Synth. Commun. 34 2004 4557
37. T. Jin, A. Wang, Z. Cheng, J. Zhang, and T. Li Synth. Commun. 35 2005 137
38. F.F.A. Latif, R. Mekheimer, E.K. Ahmed, and T.B.A. Aleem Pharmazie 48 1993 736
39. J. Deruiter, D.A. Carter, W.S. Arledge, and P.J. Sullivan J. Heterocycl. Chem. 24 1987 149
40. Z. Wang, J. Ren, and Z. Li Synth. Commun. 30 2000 763
41. L.F. Tietze, U. Beifuss, and B.M. Trost The Knoevenagel reaction Comprehensive Organic Synthesis Vol. 2 1991 Pergamon Press Oxford, UK 341
42. F. Bigi, M.L. Conforti, R. Maggi, A. Piccinno, and G. Sartori Green Chem. 2 2000 101
43. A.M. Shestopalov, A.P. Yakubov, D.V. Tsyganov, Yu.M. Emel'yanova, and V.N. Nesterov Chem. Heterocycl. Compd. 38 2002 1180
44. A.S. Golubev, P.V. Pasternak, A.F. Shidlovskii, L.N. Saveleva, B.B. Averkiev, V.N. Nesterov, M.Y. Antipin, A.S. Peregudov, and N.D. Chkanikov J. Fluorine Chem. 114 2002 63
45. -1, F(0 0 0) = 344, T = 294(2) K, R1 (I> 2σ(I)) = 0.0367, wR2 (all data) = 0.1065 for 2171 independent reflections with a goodness-of-fit of 1.036. CCDC 854873 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0) 1223 336 033; email: deposit@ccdc.cam.ac.uk ]. (see Supplementary data).
46. P. Gunasekaran Lab. Man. Microbiol. 1995 39
47. N.S. Parmer, and S. Prakash Screen. Methods Pharmacol. 2011
48. T. Mosmann J. Immunol. 65 1983 55