Novel palladium(II) and platinum(II) complexes with 1H-benzimidazol-2- ylmethyl-N-(4-bromo-phenyl)-amine: Structural studies and anticancer activity

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 399-411

  Abdel Ghani, Nour T ^a   Mansour, Ahmed M ^a  

^a CAIRO UNIVERSITY   (Egypt)

Author keywords

Benzimidazole; Biological activity; DFT; LANL2DZ; NBO

Indexed keywords

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; CISPLATIN DERIVATIVE; PALLADIUM (1H BENZIMIDAZOL 2 YLMETHYL) N (4 BROMO PHENYL) AMINE; PALLADIUM COMPLEX; PLATINUM (1H BENZIMIDAZOL 2 YLMETHYL) N (4 BROMO PHENYL) AMINE; PLATINUM COMPLEX; TETRACYCLINE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; COLON CARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; LIVER CELL CARCINOMA; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM MECHANICS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; BACTERIA; BENZIMIDAZOLES; HUMANS; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOPLATINUM COMPOUNDS; PALLADIUM; QUANTUM THEORY; SPECTRUM ANALYSIS; TEMPERATURE;

EID: 84855821171     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.11.008     Document Type: Article

References (72)

1. I.H. Krakoff M. Nicali, Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy": Clinical Application of Platinum Complexes 1988 Martinus Nijhoff Boston, MA 351
2. E.R. Jamieson, and S.J. Lippard Chem. Rev. 99 1999 2467 2498
3. I. Kostova Recent Patents Anti-Cancer Drug Discov. 1 2006 1 22
4. S. Roy, J.A. Westmaas, F. Buda, and J. Reedijk J. Inorg. Biochem. 103 2009 1278 1287
5. D. Montagner, V. Gandin, C. Marzano, and B. Longato J. Inorg. Biochem. 105 2011 919 926
6. K. Akdi, R.A. Vilaplana, S. Kamah, J.A.R. Navarro, J.M. Salas, and F. González-Vílcheza J. Inorg. Biochem. 90 2002 51
7. A. Matilla, J.M. Tercero, N.H. Dung, B. Voissat, J.M. Pérez, C. Alonso, D. Martín-Ramos, and J. Niclós-Gutiérrez J. Inorg. Biochem. 55 1994 235
8. F. Gumus, G. Eren, L. Acik, A. Celebi, F. Ozturk, R. Ilikci Sagkan, S. Gur, A. Ozkul, A. Elmali, and Y. Elerman J. Med. Chem. 52 5 2009 1345 1357
9. M. Goekce, S. Utku, S. Guer, A. Oezkul, and F. Gumus Eur. J. Med. Chem. 40 2 2005 135 141
10. F. Gumus, O. Algul, G. Eren, H. Eroglu, N. Diril, S. Gur, and A. Ozkul Eur. J. Med. Chem. 38 5 2003 473 480
11. F. Gumus, A.B. Demirci, T. Oezden, H. Eroglu, and N. Diril Pharmazie 58 5 2003 303 307
12. F. Gumus, I. Pamuk, T. Oezden, S. Yildiz, N. Diril, E. Oksuzoglu, S. Gur, and A. Ozkul J. Inorg. Biochem. 94 3 2003 255 262
13. V. Rajendiran, M. Murali, E. Suresh, S. Sinha, K. Somasundaram, and M. Palaniandavar Dalton Trans. 2008 148
14. J. Mann, A. Baron, Y. Opoku-Boahen, E. Johansson, G. Parkinson, L.R. Kelland, and S. Neidle J. Med. Chem. 44 2001 138
15. P.K. Naithani, V.K. Srivastava, A.K. Saxena, J.P. Barthwal, T.K. Gupta, and K. Shanker Indian J. Exp. Biol. 28 1990 1145
16. N.M. Goudgaon, V. Dhondiba, and A. Vijayalaxmi Indian J. Heterocycl. Chem. 13 2004 271
17. E. Bouwmann, W.L. Driessen, and J. Reedijk Coord. Chem. Rev. 104 1990 143
18. M.A. Puja, T.D. Bharamgouda, and N.D. Sathyanarayna Trans. Met. Chem. 13 1988 423
19. Phillips J. Chem. Soc. 1928 2393
20. H. Skolnik, J. Miller, and A.R. Day J. Am. Chem. Soc. 65 1943 1854
21. A. Skoog, and D.M. West Fundamentals of Analytical Chemistry 2004 Thomson, Brooks, Cole New York
22. A.L. Spek J. Appl. Cryst. 36 2003 7
23. A.L. Spek Program for Reduction of CAD-4 Data 1996 University of Utrecht The Netherlands
24. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, and M. Camalli J. Appl. Cryst. 27 1994 435
25. S. Mackay, C.J. Gilmore, C. Edwards, N. Stewart, and K. Shankland Maxus Computer Program for the Solution and Refinement of Crystal Structures 1999 Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow
26. C.K. Johnson ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program Report ORNL-5138 1976 Oak Ridge NatIonal Laboratory Oak Ridge, Tennessee, USA
27. A.D. Becke J. Chem. Phys. 98 1993 5648
28. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B. 37 1998 785
29. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, and J.A. Pople GAUSSIAN 03 (Revision A.9) 2003 Gaussian, Inc. Pittsburgh
30. A. Frisch, A.B. Nielson, and A.J. Holder GAUSSVIEW User Manual 2000 Gaussian Inc Pittsburgh, PA
31. R. Ditchfield Chem. Phys. 76 1972 5688
32. D.P. Singh, K. Kumar, and C. Sharma Eur. J. Med. Chem. 44 2009 3299 3304
33. National Committee for Clinical Laboratory Standards NCCLS Approval Standard Document M2-A7 2000 Vilanova PA
34. P. Skehan, and R. Storeng J. Natl. Cancer Inst. 42 1990 1107 1112
35. C.M. Lozano, O. Cox, M.M. Muir, J.D. Morales, J.L. Rodríguez- Cabáin, P.E. Vivas-Mejfa, and F.A. Gonzalez Inorg. Chim. Acta 271 1998 137 144
36. G. Rauhut, and P. Pulay J. Phys. Chem. 99 1995 3093 3100
37. J.A. Pople, H.B. Schlegel, R. Krishnan, J.S. Defrees, J.S. Binkley, M.J. Frisch, and R.A. Whiteside Int. J. Quantum Chem.: Quantum Chem. Symp 15 1981 269
38. M.W. Ellzy, J.O. Jensen, H.F. Hameka, J.G. Kay, and D. Zeroka Spectrochim. Acta 57A 2001 2417
39. J.O. Jensen, A. Banerjee, C.N. Merrow, D. Zeroka, and J.M. Lochner J. Mol. Struct. Theochem. 531 2000 323
40. J.O. Jensen, and D. Zeroka J. Mol. Struct. Theochem. 487 1999 267
41. O. Sala, N.S. Goncalves, and L.K. Noda J. Mol. Struct. 411 2001 565 566
42. J.R. Ferraro Low Frequency Vibrations of Inorganic and Coordination Compounds 1971 Plenum Press N. Y.
43. R.J.H. Clark, and C.S. Williams Inorg. Chem. 4 1965 350
44. K. Nakamoto Infrared and Raman Spectra of Inorganic and Coordination Compounds', Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry sixth ed. 2009 John Wiley & Sons Inc. New Jersey
45. W. Nawrocka, B. Sztuba, M.W. Kowalaka, and H. Liszkiewicz Farmaco 59 2004 83
46. E. Bednarek, J.C. Dobrowolski, K. Dobrosz-Teperek, L. Kozerski, W. Lewandowski, and A.P. Mazurek J. Mol. Struct. 554 2000 233 243
47. F.S. Miranda, F.G. Menezes, J. Vicente, A.J. Bortoluzzi, C.Z. Ademir- Neves, and N.S. Gonalves J. Mol. Struct. 938 2009 1 9
48. R.M. Issa, A.A. Hassanein, I.M. El-Mehasseb, and R.I. Abed. El-Wadoud Spectrochim. Acta Part A 65 2006 206 214
49. M. Krishnamurthy, P. Phaniraj, and S.K. Dogra J. Chem. Soc. Perkin Trans. 1986 1917 1925 (and the references therein)
50. A.K. Mishra, and S.K. Dogra Bull. Chem. Soc. Jpn. 58 1985 3587
51. J. Photochem. 31 1985 333
52. Indian J. Phys., Sect. B 54 1984 480
53. Spectrochim. Acta. Part A 39 1983 609
54. R.M. Issa, S.A. El-Daly, and N.A. El-Wakiel Spectrochim. Acta Part A 59 2003 723 728
55. C.K. Jorgensen Absorption Spectra and Chemical Bonding in Complexes 1964 Pergamon Press London
56. A.B.P. Lever Inorganic Electronic Spectroscopy second ed. 1982 Elsevier Amsterdam pp. 544-552
57. S.P. Perlepes, P. Jacobs, H.O. Desseyn, and J.M. Tasangaris Spectrochim. Acta 43A 1987 771
58. I. Lakomska, M. Barwiolek, and E. Szlyk Tran. Met. Chem. 32 2007 70
59. A. Bakalova, H. Varbanov, R. Buyukliev, G. Momekov, and D. Ivanov J. Therm. Anal. Calorimetry 95 2009 241 246
60. D.R. Lide Handbook of Chemistry and Physics second ed. 2008 CRC
61. A.W. Coats, and J.P. Redfern Nature 201 1964 68
62. H.H. Horowitz, and G. Metzger Anal. Chem. 85 1963 1464
63. B.D. Cullity Elements of X-ray Diffraction second ed. 1993 Addison-Wesley Inc.
64. N. Vijayan, R. Ramesh Babu, R. Gopalakrishnan, P. Ramasamy, and W.T.A. Harrison J. Crystal Growth 262 2004 490 498
65. D.N. Neogi, P. Das, A.N. Biswas, and P. Bandyopadhyay Polyhedron 25 2006 2149
66. R.W. Hay, T. Clifford, and P. Lightfoot Polyhedron 17 20 1998 3575 3581
67. X. Jing-Yuan, G. Wen, L. Ling, Y. Shi-Ping, C. Peng, L. Dai-Zheng, and J. Zong-Hui J. Mol. Struct. 644 2003 23 27
68. R. Wysokiński, and D. Michalska J. Comput. Chem. 22 9 2001 901 912
69. A.E. Reed, L.A. Curtiuss, and F. Weinhold Chem. Rev. 88 1988 899
70. I. Fleming Frontier Orbitals and Organic Chemical Reactions 1976 Wiley London
71. W.T. Shier Mammalian Cell Culture on $5 a Day: A Lab Manual of Low Cost Methods 1991 University of the Philippines Los Banos pp 64
72. M. Pérez-Cabré, G. Cervantes, V. Moreno, M.J. Prieto, J.M. Pérez, M. Font-Bardia, and X. Solans J. Lnorg. Biochem. 98 2004 510 521