Ferrocenyl chalcones versus organic chalcones: A comparative study of their nematocidal activity

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 6, 2011, Pages 2055-2073

  Attar, Saeed ^a   O'Brien, Zachary ^a   Alhaddad, Hasan ^a   Golden, Melissa L ^a   Calderón Urrea, Alejandro ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

Biological activity; Caenorhabditis elegans; Ferrocenyl chalcone; Nematocidal

Indexed keywords

1 (2 CHLOROPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (2 FURANYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (2 METHOXYPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (2 METHYLPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (2 THIOPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (2,4 DICHLOROPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (2,4 DIFLUOROPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (3 CHLOROPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (3,4 DIMETHOXYPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 (3,4,5 TRIMETHOXYPHENYL) 3 FERROCENYL 2 PROPEN 1 ONE; 1 FERROCENYL 3 (2 DIPHENYLPHOSPHINOPHENYL) 2 PROPEN 1 ONE; 1 FERROCENYL 3 (2 METHOXYPHENYL) 2 PROPEN 1 ONE; 1 FERROCENYL 3 (2 METHYLPHENYL) 2 PROPEN 1 ONE; CHALCONE DERIVATIVE; FERROCENYL CHALCONE DERIVATIVE; ORGANIC CHALCONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CAENORHABDITIS ELEGANS; CARBON NUCLEAR MAGNETIC RESONANCE; COMPARATIVE STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; FERTILITY; INFRARED SPECTROSCOPY; MELTING POINT; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; ANTINEMATODAL AGENTS; CAENORHABDITIS ELEGANS; CHALCONES; CRYSTALLOGRAPHY, X-RAY; FERROUS COMPOUNDS; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

CAENORHABDITIS ELEGANS; NEMATODA;

EID: 79952452030     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.01.048     Document Type: Article

References (65)

1. G. Jaouen Bioorganometallics: Biomolecules, Labeling, Medicine 2006 Wiley-VCH Weinheim
2. C.G. Hartinger, and P.J. Dyson Chem. Soc. Rev. 38 2009 391
3. N. Metzler-Nolte, and M. Salmain P. Stepnicka, Ferrocenes Ligands, Materials and Biomolecules 2008 Wiley West Sussex 499 639 Chapter 13
4. S. Top, A. Vessires, C. Cabestaing, I. Laïos, G. Leclercq, C. Provot, and G. Jaouen J. Organomet. Chem. 637-639 2001 500
5. S. Top, E.B. Kaloun, A. Vessires, I. Laïos, G. Leclercq, and G. Jaouen J. Organomet. Chem. 643-644 2002 350
6. C. Biot, G. Glorian, L. Maciejewski, and J. Brocard J. Med. Chem. 40 1997 3715
7. C. Biot, L. Delhaes, C.M. N'Diaye, L.A. Maciejewski, D. Camus, D. Dive, and J.S. Brocard Bioorg. Med. Chem. 7 1999 2843
8. C. Biot, W. Daher, C.M. Ndiaye, P. Melnyk, B. Pradines, N. Chavain, A. Pellet, L. Fraisse, L. Pelinski, C. Jarry, J. Brocard, J. Khalife, I. Forfar-Bares, and D. Dive J. Med. Chem. 49 2006 4707
9. D.N. Dahr The Chemistry of Chalcones and Related Compounds 1981 Wiley New York
10. M. Liu, P. Wilairat, and M.-L. Go J. Med. Chem. 44 2001 4443
11. P.M. Sivakumar, S. Priya, and M. Doble Chem. Biol. Drug Des. 73 2009 403
12. J. Quintin, J. Desrivot, S. Thoret, P. Le Menez, T. Cresteil, and G. Lewin Bioorg. Med. Chem. Lett. 19 2009 167
13. M. Al Rahim, A. Nakajima, N. Misawa, K. Shindo, K. Adachi, Y. Shizuri, Y. Ohizumi, and T. Yamakuni Eur. J. Pharmacol. 600 2008 10
14. M.V.B. Reddy, C.-R. Su, W.-F. Chiou, Y.-N. Liu, R.Y.-H. Chen, K.F. Bastow, K.-H. Lee, and T.-S. Wu Bioorg. Med. Chem. 16 2008 7358
15. R.N. Gacche, N.A. Dhole, S.G. Kamble, and B.P. Bandgar J. Enzyme Inhib. Med. Chem. 23 2008 28
16. E.H. Alberton, R.G. Damazio, L.H. Cazarolli, L.D. Chiaradia, P.C. Leal, R.J. Nunes, R.A. Yunes, and F.R.M.B. Silva Chem. Biol. Interact. 171 2008 355
17. H. Nozaki, K.-I. Hayashi, M. Kido, K. Kakumoto, S. Ikeda, N. Matsuura, H. Tani, D. Takaoka, M. Iinuma, and Y. Akao Tetrahedron Lett. 48 2007 8290
18. J. Deng, T. Sanchez, L.Q. Al-Mawsawi, R. Dayam, R.A. Yunes, A. Garofalo, M.B. Bolger, and N. Neamati Bioorg. Med. Chem. 15 2007 4985
19. M. Cabrera, M. Simoens, G. Falchi, M.L. Lavaggi, O.E. Piro, E.E. Castellano, A. Vidal, A. Azqueta, A. Monge, and A. Lopez de Cerain Bioorg. Med. Chem. 15 2007 3356
20. P.M. Sivakumar, S.K.G. Babu, and D. Mukesh Chem. Pharm. Bull. 55 2007 44
21. N.J. Lawrence, R.P. Patterson, L.-L. Ooi, D. Cook, and S. Ducki Bioorg. Med. Chem. Lett. 16 2006 5844
22. J. Biochard, and J. Tirouflet Compt. Rend. 251 1960 1394
23. M. Frudik, and S. Toma Chem. Zvesti 20 1966 326
24. A. Perjessy Chem. Zvesti 23 1969 343
25. X. Wu, P. Wilairat, and M.-L. Go Bioorg. Med. Chem. Lett. 12 2002 2299
26. X. Wu, E.R.T. Tiekink, I. Kostetski, N. Kocherginsky, A.L.C. Tan, S.B. Khoo, P. Wilairat, and M.-L. Go Eur. J. Pharm. Sci. 27 2006 2175
27. V. Zsoldos-Mády, A. Csámpai, R. Szabó, E. Mészáros-Alapi, J. Pásztor, F. Hudecz, and P. Sohár ChemMedChem 1 2006 1119
28. D.J. Chitwood Annu. Rev. Phytopathol. 40 2002 221
29. D.M. Bird, and I. Kaloshian Physiol. Mol. Plant Pathol. 62 2003 115
30. W. Thomas Atmos. Environ. 30 1996 1
31. (b) US Environmental Protection Agency Home Page. http://www.epa.gov/ Ozone/mbr (accessed July 2009).
32. C.S. Norman J. Environ. Manage. 75 2005 167
33. C.S. Norman, S.J. DeCanio, and L. Fan Global Environ. Chang. 18 2008 330
34. R. Laliberté, D. Campbell, and F. Brauderlein Can. J. Pharm. Sci. 2 1967 37
35. J.A. González, and A. Estévez-Braun Pestic. Biochem. Phys. 58 1997 193
36. J.A. González, and A. Estévez-Braun J. Agric. Food Chem. 46 1998 1163
37. (a) The University of Texas Southwestern Medical Center at Dallas, Caenorhabditis elegans WWW Server Home Page. http://elegans.swmed.edu (accessed July 2009).
38. C. Britton, and L. Murray Int. J. Parasitol. 36 2006 651
39. K. Noack, and N. Jones Can. J. Chem. 39 1961 2225
40. N.L. Silver, and D.W. Boykin Jr. J. Org. Chem. 35 1970 759
41. A.G. Nagy, and P. Sohar J. Organomet. Chem. 390 1990 217
42. G. Venkateshwarlu, and B. Subrahmanyam Proc. Indian Acad. Sci. (Chem. Sci.) 102 1990 45
43. R.A. Nyquist, Interpreting Infrared, Raman, and Nuclear Magnetic Resonance Spectra 2001 Academic Press London Chapter 14
44. G. Thirunarayanan, M. Gopalakrishnan, and G. Vanangamudi Spectrochim. Acta, Part A 67 2007 1106
45. L.J. Yamin, E.I. Gasull, S.E. Blanco, and F.H. Ferretti J. Mol. Struct. (Theochem) 428 1998 167
46. M.L. Go, X. Wu, and X.L. Liu Curr. Med. Chem. 12 2005 483
47. M. Larsen, H. Kromann, A. Kharazmi, and S. Feldbaek Nielsen Bioorg. Med. Chem. Lett. 15 2005 4858
48. S. Ducki, R. Forrest, J.A. Hadfield, A. Kendall, N.J. Lawrence, A.T. McGown, and D. Rennison Bioorg. Med. Chem. Lett. 8 1998 1051
49. Chemical Abstracts™ and SciFinder Scholar™ services are available through the Chemical Abstracts Service (CAS, www.cas.org ), a division of the American Chemical Society. These services are available through a site license at the California State University, Fresno.
50. K.-I. Son, and D.-Y. Noh J. Korean Chem. Soc. 51 2007 591
51. Y.J. Jung, K.-I. Son, Y.E. Oh, and D.-Y. Noh Polyhedron 27 2008 861
52. S.-K. Lee, Y.-S. Noh, K.-I. Son, and D.-Y. Noh Inorg. Chem. Commun. 13 2010 1343
53. R. Benassi, U. Folli, D. Larossi, L. Schenetti, F. Taddei, A. Musatti, and M. Nardelli Chem. Soc., Perkin Trans. 2 1989 1741
54. S. Hekimi, B. Lakowski, T. Barnes, and J. Ewbank Trends Genet. 14 1998 14
55. Y. Xue, and X. Gong J. Mol. Struct. (Theochem) 901 2009 226 and references cited therein
56. V. Opletalova, J. Hartl, K. Palat Jr., and A. Patel J. Pharm. Biomed. Anal. 23 2000 55
57. spartan '08 for Mac™; Wavefunction Inc.: Irvine, CA (http://www.wavefun.com ).
58. N. Motohashi, T. Kurihara, W. Yamanaka, K. Satoh, H. Sakagami, and J. Molnar Anticancer Res. 17 1997 3431
59. T. Kurihara, N. Motohashi, H. Sakagami, and J. Molnar Anticancer Res. 19 1999 4081
60. J.L. Lopez-Perez, E. del Plmo, B. de Pascual-Teresa, M. Merino, M. Barajas, and A. San Feliciano J. Mol. Struct. (Theochem) 504 2000 51
61. A. Shah, R. Qureshi, A.M. Khan, F.L. Ansari, and S. Ahmad Bull. Chem. Soc. Jpn. 82 2009 453
62. M.-L. Go, M. Liu, P. Wilairat, S.L. Croft, and A.L. Tan Bioorg. Med. Chem. 11 2003 2729
63. S.F. Nielsen, A. Kharazmi, and S.B. Christensen Bioorg. Med. Chem. 6 1998 937
64. M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, L. De Caro, C. Gaicovazzo, G. Polidori, and R. Spagna J. Appl. Crystallogr. 38 2005 381
65. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112