Synthesis, crystal structures and antibacterial activity studies of aza-derivatives of phytoalexin from cotton plant - gossypol

European Journal of Medicinal Chemistry

Volumn 44, Issue 11, 2009, Pages 4393-4403

  Przybylski, Piotr ^a   Pyta, Krystian ^a   Stefańska, Joanna ^b   Ratajczak Sitarz, Małgorzata ^a   Katrusiak, Andrzej ^a   Huczyński, Adam ^a   Brzezinski, Bogumil ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Antibacterial activity; Gossypol aza derivatives; Spectroscopy; Tautomerism; X ray

Indexed keywords

GOSSYPOL DERIVATIVE; HYDRAZONE DERIVATIVE; PHYTOALEXIN; SCHIFF BASE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BACILLUS SUBTILIS; BORDETELLA BRONCHISEPTICA; CANDIDA ALBICANS; CANDIDA PARAPSILOSIS; COTTON; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS HIRAE; ESCHERICHIA COLI; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTEUS VULGARIS; PSEUDOMONAS AERUGINOSA; SEED; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CRYSTALLOGRAPHY, X-RAY; GOSSYPIUM; GOSSYPOL; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HYDRAZONES; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; SCHIFF BASES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; YEASTS;

EID: 70349902333     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.05.032     Document Type: Article

References (72)

1. Benedict C.R., Martin G.S., Liu J., Puckhaber L., and Magill C.W. Phytochemistry 65 (2004) 1351-1359
2. Dodou K. Exp. Opin. Invest. New Drug 14 (2005) 1419-1434
3. Lin T.-S., Schinazi R.F., Zhu J., Birks E., Carbone R., Si Y., Wu K., Huang L., and Prusoff W.H. Biochem. Pharmacol. 46 (1993) 251-255
4. Royer R.E., Deck L.M., Vander Jagt T.J., Martinez F.J., Mills R.G., Young S.A., and Vander Jagt D.L. J. Med. Chem. 38 (1995) 2427-2432
5. Pacheco L.B., Castro-Garza J., Perez-Eguia E., Zepeda-Herrera H., Chico-Mijares K., Carranza-Rosales M.P., Said-Fernandez S., and Gonzalez-Garza M.T. Pharm. Sci. 2 (1996) 333-334
6. Lin T.S., Schinazi R., Griffith B.P., August E.M., Eriksson B.F.H., Zgeng D.-K., Huang L., and Prusoff W.H. Antimicrob. Agents Chem. 33 (1989) 2149-2151
7. Hu Y.-F., Chang C.-J.G., Brueggemeier R.W., and Lin Y.C. Cancer Lett. 87 (1994) 17-23
8. Coyle T., Levante S., Shetler M., and Winfield J. J. Neuro-oncol. 19 (1994) 25-35
9. Ye W., Chang H.-L., Wang L.-S., Huang Y.-W., Shu S., Dowd M.K., Wan P.J., Sugimoto Y., and Lin Y.C. Anticancer Res. 27 (2007) 107-116
10. Mace M.E., Stipanovic R.D., and Bell A.A. Nat. Toxins 1 (1993) 294-295
11. Abraham K.J., Pierce M.L., and Essenberg M. Phytochemistry 52 (1999) 829-836
12. Kovaci P. Curr. Med. Chem. 10 (2003) 2711-2718
13. Kenar J.A. J. Am. Oil Chem. Soc. 83 (2006) 269-302
14. Przybylski P., and Brzezinski B. Biopolymers (Biospectroscopy) 67 (2002) 61-69
15. Dao V.-T., Dowd M.K., Gaspard C., Martin M.-T., Hećmez J., Laprećvote O., Mayer M., and Michelot R.J. Bioorg. Med. Chem. 11 (2003) 2001-2006
16. Rezhepov K.Zh., Ziyaev Kh.L., Baram N.I., Kamaev F.G., Levkovich M.G., Saiitkulov A.M., and Ismailov A.I. Chem. Nat. Compd. 39 (2003) 358-361
17. Dao V.-T., Dowd M.K., Martin M.-T., Gaspard C., Mayer M., and Michelot R.J. Eur. J. Med. Chem. 39 (2004) 619-624
18. Quang T.T., Nguyen K.P.P., and Hansen P.E. Magn. Res. Chem. 43 (2005) 302-308
19. Przybylski P., Schilf W., Lewandowska W., and Brzezinski B. Biopolymers 83 (2006) 213-225
20. Dodou K., Anderson R.J., Lough W.J., Small D.A.P., Shelley M.D., and Groundwater P.W. Bioorg. Med. Chem. 13 (2005) 4228-4237
21. Razakantoanina V., Phung N.K.P., and Jaureguiberry G. Parasitol. Res. 86 (2000) 665-668
22. Liang X.S., Rogers A.J., Webber C.L., Ormsby T.J., Tiritan M.E., Matlin S.A., and Benz C.C. Invest. New Drug 13 (1995) 181-186
23. Shelley M.D., Hartley L., Groundwater P.W., and Fish R.G. Anti-cancer Drugs 11 (2000) 209-216
24. Rezhepov K.Zh., Ziyaev Kh.L., Baram N.I., Ismailov A.I., Kamaev F.G., and Saiitkulov A.M. Chem. Nat. Compd. 38 (2002) 319-322
25. Royer R.E., Mills R.G., Young S.A., and Vander Jagt D.L. Pharmacol. Res. 31 (1995) 49-52
26. Yildirim-Aksoy M., Lim C., Dowd M.K., Wan P.J., Klesius P.H., and Shoemaker C. J. Appl. Microbiol. 97 (2004) 87-92
27. Tegos G., Stermitz F.R., Lomovskaya O., and Lewis K. Antimicrob. Agents Chem. 46 (2002) 3133-3141
28. Boonsri S., Karalai Ch., Ponglimanot Ch., Chantrapromma S., and Kanjana-Opas A. J. Nat. Prod. 71 (2008) 1173-1177
29. Essenberg M., Doherty M.d.'A., Hamilton B.K., Henning B.T., Cover E.C., McFaul S.J., and Johnson W.M. Phytopathology 72 (1982) 1349-1356
30. Essenberg M., Pierce M.L., Hamilton B., Cover E.C., Scholes V.E., and Richardson P.E. Physiol. Mol. Plant Pathol. 41 (1992) 85-99
31. Przybylski P., Pyta K., Ratajczak-Sitarz M., Katrusiak A., and Brzezinski B. Struct. Chem. 19 (2008) 983-995
32. Przybylski P., Bartl F., and Brzezinski B. Biopolymers 65 (2002) 111-120
33. Przybylski P., Bejcar G., Huczyński A., Schroeder G., Brzezinski B., and Bartl F. Biopolymers 82 (2006) 521-535
34. Przybylski P., Schroeder G., and Brzezinski B. Phys. Chem. Chem. Phys. 4 (2002) 6137-6143
35. Przybylski P., Schroeder G., and Brzezinski B. J. Mol. Struct. 699 (2004) 65-77
36. Dao V.-T., Gaspard C., Mayer M., Werner G.H., Nguyen S.N., and Michelot R.J. Eur. J. Med. Chem. 35 (2000) 805-813
37. Matlin S.A., Roshdy S., Cass Q.B., Freitas L.C.G., Longo R.L., and Malvestiti I. J. Braz. Chem. Soc. 1 (1990) 128-135
38. Przybylski P., Schilf W., Kamieński B., Brzezinski B., and Bartl F. Magn. Res. Chem. 46 (2008) 534-544
39. Beketov K.M., Talipov S.A., Ibragimov B.T., Praliev K.D., and Aripov T.F. Kristallografiya (Russ.) 48 (2003) 691-694
40. Przybylski P., Ratajczak-Sitarz M., Katrusiak A., Wojciechowski G., Schilf W., and Brzezinski B. J. Mol. Struct. 655 (2003) 293-300
41. Gdaniec M. J. Incl. Phenom. Macrocycl. Chem. 17 (1994) 365-376
42. Talipov S.A., Ibragimov B.T., Izotova L.Yu., Tilyakov Z.G., and Dalimov D.N. Khim. Prir. Soedin. (Russ.) (2004) 422-424
43. Przybylski P., Pyta K., Wicher B., Gdaniec M., and Brzezinski B. J. Mol. Struct. 889 (2008) 332-343
44. Wouters J., Luque F.J., Barretta G.U., Balzano F., Pignatello R., and Guccione S. J. Chem. Soc., Perkin Trans 2 5 (2002) 1012-1016
45. Grabowski S.J. J. Mol. Struct. TEOCHEM 811 (2007) 61-67
46. Sobczyk L., Grabowski S.J., and Krygowski T.M. Chem. Rev. 105 (2005) 3513-3560
47. Filarowski A., Kochel A., Cieslik K., and Koll A. J. Phys. Org. Chem. 18 (2005) 986-993
48. Rozwadowski Z., Schilf W., and Kamieński B. Magn. Res. Chem. 43 (2005) 573-577
49. Zundel G. J. Mol. Struct. 552 (2000) 81-86
50. Przybylski P., Brzezinski B., and Bartl F. Biopolymers 74 (2004) 273-286
51. Bohlmann F. Chem. Ber. 91 (1958) 2157-2159
52. Masamune T., Takasugi M., and Matsuki M. Bull. Chem. Soc. Jpn. 41 (1968) 2466-2469
53. Konarski J. J. Mol. Struct. 7 (1971) 337-354
54. Brycki B., Brzezinski B., Marciniak B., and Paszyc S. Spectrosc. Lett. 24 (1991) 509-518
55. Przybylski P., Kira J., Schroeder G., Brzezinski B., and Bartl F. J. Phys. Chem. A 112 (2008) 8061-8069
56. Schilf W., Kamienski B., Szady-Chełmieniecka A., Grech E., Makal A., and Wozniak K. J. Mol. Struct. 844-845 (2007) 94-101
57. Dziembowska T., Hansen P.E., and Rozwadowski Z. Prog. Nucl. Magn. Reson. Spectrosc. 45 (2004) 1-29
58. Siddiqui B.S., Ali S.T., Rasheed M., and Kardar M.N. Helv. Chim. Acta 86 (2003) 2787-2796
59. O'Brien D.H., and Stipanovic R.D. J. Org. Chem. 43 (1978) 1105-1111
60. Salas C., Armstrong V., Lopez C., and Tapia R.A. Magn. Res. Chem. 46 (2008) 191-194
61. Rozwadowski Z. J. Mol. Struct. 753 (2005) 127-135
62. Douglas J.D., Senior S.J., Morehouse C., Phetsukiri B., Campbell I.B., Besra G.S., and Minnikin D.E. Microbiology 148 (2002) 3101-3109
63. Lourenco M.C.S., Vicente F.R., Henriques M.d.G.M.d.O., Peixoto Candea A.L., Borges Goncalves R.S., Nogueira T.C.M., de Lima Ferreira M., and Nora de Souza M.V. Bioorg. Med. Chem. Lett. 17 (2007) 6895-6898
64. Yuldasheva L.N., Cruz e Carvalho A., and Krasilnikov O.V. J. Incl. Phenom. Macrocycl. Chem. 60 (2008) 65-70
65. Medina L.F.C., Stefani V., and Brandelli A. Lett. Appl. Microbiol. 42 (2006) 381-385
66. Adams R., Morris R.C., Geissman T.A., Butterbaugh D.J., and Kirkpatrick K.C. J. Am. Chem. Soc. 60 (1938) 2193-2194
67. Przybylski P., Brzezinski B., and Bartl F. J. Mol. Struct. 794 (2006) 237-243
68. Przybylski P., Małuszyńska M., and Brzezinski B. J. Mol. Struct. 750 (2005) 152-157
69. Bejcar G., Przybylski P., Walkowiak M., and Brzezinski B. J. Mol. Struct. 830 (2007) 72-77
70. Bejcar G., Przybylski P., Fusiara J., Brzezinski B., and Bartl F. J. Mol. Struct. 754 (2005) 31-36
71. Sheldrick G. SHELXS-97, Program for Crystal Structure Solution (1997), University of Goettingen
72. Sheldrick G. SHELXL-97, Program for Crystal Structure Refinement (1997), University of Goettingen