A facile sequential three-component regio- and stereoselective synthesis of novel spiro-isoxazoline/acridinone hybrids

Tetrahedron Letters

Volumn 53, Issue 51, 2012, Pages 6885-6888

  Uma Maheswari, Shanmugavel ^a   Perumal, Subbu ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

1,3 Dipolar cycloaddition; 3,4 Dihydroacridin 1(2H) one; Nitrile oxides; Spiroisoxazolyl acridinones

Indexed keywords

3,4 DIHYDROACRIDIN 1(2H) ONE; ACRIDONE DERIVATIVE; ALDEHYDE; BENZOHYDROXIMINOYL CHLORIDE; CHLORIDE; ISOXAZOLINE DERIVATIVE; POTASSIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; KNOEVENAGEL CONDENSATION; ONE POT SYNTHESIS; STEREOCHEMISTRY;

EID: 84869236464     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.09.105     Document Type: Article

References (67)

1. A.G. Habeeb, P.N.P. Rao, and E. Knaus Eur. J. Med. Chem. 44 2001 2921
2. Rakesh, D. Sun, R.B. Lee, R.P. Tangallapally, and R.E. Lee Eur. J. Med. Chem. 44 2009 460
3. R.P. Tangallapally, D. Sun, Rakesh, N. Budha, R.E.B. Lee, A.J.M. Lenaerts, B. Meibohm, and R.E. Lee Bioorg. Med. Chem. Lett. 17 2007 6638
4. D. Basappa, M.P. Sadashiva, K. Mantelingu, S.N. Swamy, and K.S. Rangappa Bioorg. Med. Chem. 11 2003 4539
5. H. Kai, H. Matsumoto, N. Hattori, A. Takase, T. Fujiwara, and H. Sugimoto Bioorg. Med. Chem. Lett. 2001 1997 11
6. M.C. Pirrung, L.N. Tumey, C.R.H. Raetz, J.E. Jackman, K. Snehalatha, A.L. McClerren, C.A. Fierke, S.L. Gantt, and K.M. Rusche J. Med. Chem. 45 2002 4359
7. P. Conti, M.D. Amici, G. Roda, G. Vistoli, T.B. Stensbol, H. Bräuner-Osborne, U. Madsen, L. Toma, and C.D. Micheli Tetrahedron 59 2003 1443
8. J.R. Pruitt, D.J. Pinto, M.J. Estrella, L.L. Bostrom, R.M. Knabb, P.C. Wong, M.R. Wright, and R.R. Wexler Bioorg. Med. Chem. Lett. 10 2000 685
9. D.G. Martin, D.J. Duchamp, and C.G. Chidester Tetrahedron Lett. 14 1973 2549
10. W.C. Groutas, R. Venkataramam, L.S. Chong, J.E. Yoder, J.B. Epp, M.A. Stanga, and E.-H. Kim Bioorg. Med. Chem. 3 1995 125
11. F. Lepage, F. Tombert, G. Cuvier, A. Marivain, and J.M. Gillardin Eur. J. Med. Chem. 27 1992 581
12. S. Ryng, Z. Machon, Z. Wieczorek, M. Zimecki, and M. Mokrosz Eur. J. Med. Chem. 33 1998 831
13. B. Badio, H.M. Garraffo, C.V. Plummer, W.L. Padgett, and J.W. Daly Eur. J. Pharmacol. 26 1997 89
14. F. Ivy Carroll Bioorg. Med. Chem. Lett. 14 2004 1889
15. S. Srivastava, L.K. Bajpai, S. Batra, A.P. Bhaduri, J.P. Maikhur, G. Gupta, and J.D. Dhar Bioorg. Med. Chem. 7 1999 2607
16. G. Dannahardt, W. Kiefer, G. Kramer, S. Maehrlein, U. Nowe, and B. Fiebich Eur. J. Med. Chem. 35 2000 499
17. R.P. Tangallapally, R. Yendapally, A.J. Daniels, R.E.B. Lee, and R.E. Lee Curr. Top. Med. Chem. 7 2007 509
18. P.R. Berquist, and R.J. Wells Chemotaxonomy of the Porifera: The Development and Current Status of the Field P.J. Scheuer, Marine Natural Products Chemical and Biological Perspectives Vol. 5 1993 Academic Press New York 1 50
19. D.J. Faulkner Nat. Prod. Rep. 1998 113
20. D.J. Faulkner Nat. Prod. Rep. 1997 259
21. J. Faulkner Nat. Prod. Rep. 18 2001 1
22. T.R. Boehlow, and C.D. Spilling Nat. Prod. Lett. 7 1995 1
23. J.D. Faulkner Nat. Prod. Rep. 19 2002 1
24. R.D. Encarnacion, E. Sandoval, J. Malmstrom, and C. Christophersen J. Nat. Prod. 63 2000 874
25. M.R. Kernan, R.C. Canbie, and P.R. Bergquist J. Nat. Prod. 53 1990 615
26. R.S. Compagnone, R. Avila, A.I. Suarez, O.V. Abrams, H.R. Rangel, F. Arvelo, I.C. Pina, and E. Merentes J. Nat. Prod. 62 1999 1443
27. P. Caramella, and P. Grunanger A. Padwa, 1,3-Dipolar Cycloaddition Chemistry Vol. 1 1984 Wiley New York NY 291 392 Chapter 3
28. I. Kudyba, J. Jozwik, J. Romanski, J. Raczko, and J. Jurczak Tetrahedron: Asymmetry 16 2005 2257
29. K.B.G. Torssell Nitrile Oxides Nitrones and Nitronates in Organic Synthesis 1988 VCH Weinheim
30. P. Grunanger, and P. Vita-Finzi Isoxazoles-Part 1 Chemistry of Heterocyclic Compounds Vol. 49 1991 Wiley New York NY
31. M. Demeunynck Expert Opin. Ther. Patents 14 2004 55
32. Z. Topcu J. Clin. Pharm. Ther. 26 2001 405
33. S.R. Kirk, N.W. Luedtke, and Y. Toy J. Am. Chem. Soc. 122 2000 980
34. A. Albert The Acridine 1966 Edward Arnold London, UK
35. W.D. Inman, M. O'Neill-Johnson, and P. Crews J. Am. Chem. Soc. 112 1990 1
36. E. Gimenez-Arnau, S. Missailids, and M.F.G. Stevens Anti-Cancer Drug Res. 13 1998 431
37. R.T.D. Oliver Curr. Opin. Oncol. 13 2001 191
38. E.T. Martins, H. Baruah, J. Kramarczyk, G. Saaluta, C.S. Day, G.L. Kucera, and U. Bierbach J. Med. Chem. 44 2001 4492
39. F. Hamy, V. Brondani, A. Florsheimer, W. Stark, M.J.J. Blommers, and T. Klimkait Biochemistry 37 1998 5086
40. B.F. Cain, and G.J. Atwell Eur. J. Cancer. 10 1974 539
41. J. Hornedo, and D.A. Van Echo Pharmacotherapy 5 1985 78
42. H. Malonne, and G. Atassi Anticancer Drugs 8 1997 811
43. D. Greenwood J. Antimicrob. Chemother. 36 1995 857
44. D. Fyfe, F. Raynaud, R.E. Langley, D.R. Newell, G. Halbert, C. Gardner, K. Clayton, P.J. Woll, I. Judson, and J. Carmichael Cancer Chemother. Pharmacol. 49 2002 1
45. S.T. Brennan, N.L. Colbry, R.L. Leeds, B. Leja, S.R. Priebe, M.D. Reily, H.D.H. Showalter, S.E. Uhlendorf, G.J. Atwell, and W.A. Denny J. Heterocycl. Chem. 26 1989 1469
46. M. Gniazdowski, and L. Szmigiero General Pharmacol. 26 1995 473
47. W.K. Summers, L.V. Majouski, G.M. Marsh, K. Tachiki, and A. Kling Engl. J. Med. 315 1986 1241
48. S.U. Maheswari, S. Perumal, and A.I. Almansour Tetrahedron Lett. 53 2012 349
49. R. Suresh Kumar, S. Michael Rajesh, S. Perumal, P. Yogeeswari, and D. Sriram Tetrahedron: Asymmetry 21 2010 1315
50. R. Ranjth Kumar, and S. Perumal Tetrahedron 63 2007 12220
51. R. Ranjith Kumar, and S. Perumal Tetrahedron 63 2007 7850
52. R. Suresh Kumar, S. Perumal, H.B. Kagan, and R. Guillot Tetrahedron: Asymmetry 18 2007 170
53. R. Ranjith Kumar, S. Perumal, H.B. Kagan, and R. Guillot Tetrahedron 62 2006 12380
54. P. Gunasekaran, K. Balamurugan, S. Sivakumar, S. Perumal, J.C. Menéndez, and A.I. Almansour Green Chem. 14 2012 750
55. S. Michael Rajesh, S. Perumal, J.C. Menéndez, S. Pandian, and R. Murugesan Tetrahedron 68 2012 5631
56. S. Perumal, J. C. Menéndez, in: O. A. Attanasi, D. Spinelli (Eds.), Targets in Heterocyclic Systems Chemistry and Properties; Arti Grafiche Editoriali s.r.l.: Italy, 2011; Vol. 15, pp. 402-422.
57. P.S. Harikrishnan, S. Michaelrajesh, and S. Perumal Tetrahedron Lett. 53 2012 3880
58. B.M. Vinosha, S. Perumal, S. Renuga, and A.I. Almansour Tetrahedron Lett. 53 2012 962
59. S. Muthusaravanan, S. Perumal, and A.I. Almansour Tetrahedron Lett. 53 2012 1144
60. S. Indumathi, S. Perumal, and J.C. Menéndez J. Org. Chem. 75 2010 472
61. For selected reviews of diversity-oriented synthesis, see: M.D. Burke, and S.L. Schreiber Angew. Chem., Int. Ed. 43 2004 46
62. D.S. Tan Nat. Chem. Biol. 1 2005 74
63. R.J. Spandl, A. Bender, and R.D. Spring Org. Biomol. Chem. 6 2008 1149
64. L. Weber Curr. Med. Chem. 9 2002 2085
65. C. Hulme, and V. Gore Curr. Med. Chem. 10 2003 51
66. V. Sridharan, P. Ribelles, T. Ramos, and J.C. Menéndez J. Org. Chem. 74 2009 5715
67. Crystallographic data (excluding structure factors) for compound 4e in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 885181. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ].