Molecular structures and antiproliferative activity of side-chain saturated and homologated analogs of 2-chloro-3-(n-alkylamino)-1,4-napthoquinone

Journal of Molecular Structure

Volumn 1049, Issue , 2013, Pages 355-361

  Pal, Sanjima ^a   Jadhav, Mahesh ^b   Weyhermüller, Thomas ^c   Patil, Yogesh ^d   Nethaji, M ^d   Kasabe, Umesh ^b   Kathawate, Laxmi ^b   Badireenath Konkimalla, V ^a   Salunke Gawali, Sunita ^b  

^a NATIONAL INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

^b UNIVERSITY OF PUNE   (India)

^c MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^d INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Aminonaphthoquinone; Antiproliferative activity; Hydrogen bonding; stacking

Indexed keywords

BRAIN; CHAINS; DIMERS; HYDROGEN BONDS; KETONES; POLYMERS; ULTRAVIOLET VISIBLE SPECTROSCOPY; X RAY DIFFRACTION;

AMINONAPHTHOQUINONE; ANTI-PROLIFERATIVE; ANTI-PROLIFERATIVE ACTIVITIES; OPTIMAL ACTIVITY; SINGLE CRYSTAL X-RAY STRUCTURES; SINGLE-CRYSTAL X-RAY DIFFRACTION STUDIES; TISSUE SPECIFICS; UV VISIBLE SPECTROSCOPY;

SINGLE CRYSTALS;

EID: 84885124881     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2013.06.062     Document Type: Article

References (52)

1. E.N. da Silva Junior, C.F. de Deus, B.C. Cavalcanti, C. Pessoa, L.V. CostaLotufo, R.C. Montenegro, M.O. de Moraes, M.F.R. Pinto, C.A. de Simone, V.F. Ferreira, M.O.F. Goulart, C.K.Z. Andrade, A. Pinto, J. Med. Chem. 53 (2010) 504-508
2. V.K. Tandon, H.K. Maurya, N.N. Mishra, P.K. Shukla, Eur. J. Med. Chem. 44 (2009) 3130-3137
3. S. Ganapaty, P.S. Thomas, G. Karagianis, P.G. Waterman, R. Brun, Phytochemistry 67 (2006) 1950-1956
4. T.M.S. Silva, C.S. Camara, T.P. Barbosa, A.Z. Soares, L.C. da Cunha, A.C. Pinto, M.D. Vargas, Bioorg. Med. Chem. 13 (2005) 193-196
5. C. Biot, H. Bauer, R.H. Schirmer, E. Davioud-Charret, J. Med. Chem. 47 (2004) 5972-5983.
6. D.R. da Rocha, A.C.G. de Souza, J.A.L.C. Resende, W.C. Santos, E.A. dos Santos, C. Pessoa, M.O. de Moraes, L.V. Costa-Lotufo, R.C. Montenegro, V.F. Ferreira, Org. Biomol. Chem. 9 (2011) 4315-4322
7. V.R. Campos, E.A. dos Santos, V.F. Ferreira, R.C. Montenegro, M.C.B.V. De Souza, L.V. Costa-Lotufo, M.O. de Moraes, A.K.P. Regufe, A.K. Jordao, A.C. Pinto, J.A.L.C. Resende, A.C. Cunha, RSC Advances 2 (2012) 11438-11448
8. S.J. Lucas, R.M. Lord, R.L. Wilson, R.M. Phillips, V. Sridharan, P.C. McGowan, Dalton Trans. 41 (2012) 13800-13802
9. E. Perez-Sacau, R.G. Diaz-Penate, A. Estevez-Braun, A.G. Ravelo, J.M. Garcia-Castellano, L. Pardo, M. Campillo, J. Med. Chem. 50 (2007) 696-706
10. K.K.C. Liu, J. Li, S. Sakya, Mini-Rev. Med. Chem. 4 (2004) 1105-1125
11. Y. Kumagai, Y. Shinkai, T. Miura, A.K. Cho, Annu. Rev. Pharmacol. 52 (2012) 221-247
12. M. Hallak, B.K. Thakur, Winn, O. Shpilberg, S. Bittner, Y. Granot, I. Levy, L. Nathan, Anticancer Research 33 (2013) 183-190.
13. A. Ventura Pinto, S. Lisboa de Castro, Molecules 14 (2009) 4570-4590.
14. V.K. Tondon, R.B. Chhor, R.V. Singh, S. Rai, D.B. Yadav, Bioorg. Med. Chem. Lett. 14 (2004) 1079-1083.
15. C.K. Ryu, J.Y. Shim, M.J. Chae, I.H. Choi, J. Han, O. Jung, J.Y. Lee, S.H. Jeong, Eur. J. Med. Chem. 40 (2005) 438-444.
16. V.K. Tondon, H.K. Maurya, N.N. Mishra, P.K. Shulka, Eur. J. Med. Chem. 44 (2009) 3130-3137.
17. (a) M.W. Singh, A. Karmarkar, N. Barooah, J.B. Baruah, Belestein J. Org. Chem. 3 (2007) 10
18. S. Salunke-Gawali, L. Kathawate, Y. Shinde, V.G. Puranik, J. Mol. Struct. 1010 (2012) 38-45
19. S. Rane, K. Ahmed, S. Salunke-Gawali, S.B. Zaware, D. Srinivas, R. Gonnade, M. Bhadbhade, J. Mol. Struct. 892 (2008) 74-83
20. S. Salunke-Gawali, S.Y. Rane, V.G. Puranik, C. Guyard-Duhayan, F. Varret, Polyhedron 23 (2004) 2541-2547.
21. D.D. Perrin, W.L. Armarego, D.R. Perrin, Purification of Laboratory Chemicals, Pergamon Press, London, 1988. pp 260.
22. G.M. Sheldrick, SADABS, Bruker-Siemens Area Detector Absorption and Other Correction, University of Göttingen, Germany, 2006, Version 2008/1.
23. ShelXTL 6.14 Bruker AXS Inc., Madison, WI, USA 2003.
24. G.M. Sheldrick, SHELX-97 Program for crystal structure solution and refinement, University of Göttingen, Germany, 1997.
25. V.B. Konkimalla, T. Efferth, Biochem. Pharmacol 15 (2010) 1092-1099.
26. A.T. Dharmaraja, T.K. Dash, V.B. Konkimalla, H. Chakrapani, Med. Chem. Commun. 3 (2012) 219-224.
27. V.F. Ferreira, S.B. Ferreira, F. de Carvalho da Silva, Org. Biomol. Chem. 8 (2010) 4793-4802.
28. (a) T.J. Monks, D.C. Jones, Curr. Drug Metab. 3 (2002) 425-438
29. E.V.M. Santos, J.W.M. Carneiro, V.F. Ferreira, Bioorg. Med. Chem. 12 (2004) 87-93
30. A. Brunmark, E. Cadenas, Free Radical. Biol. Med. 7 (1989) 435-477
31. T.J. Monks, R.P. Hanslik, G.M. Cohen, D. Ross, D.G. Graham, Toxicol. Appl. Pharmacol. 112 (1992) 2-16
32. J.L. Bolton, M.A. Trush, T.M. Penning, G. Dryhurst, T.J. Monks, Chem. Res. Toxicol. 13 (2000) 135-160
33. A.B. Pardee, Y.Z. Li, C.J. Li, Curr. Cancer Drug Targets 2 (2002) 227-242
34. S.B. Ferreira, D.T.G. Gonzaga, W.C. Santos, K.G.L. Araujo, V.F. Ferreira, Rev. Virtual Quim. 2 (2010) 140-160
35. M.N. da Silva, V.F. Ferreira, M.C.B.V. de Souza, Quim. Nova 26 (2003) 407-416.
36. V.H.J. Frade, M.J. Sousa, J.C.V.P. Moura, M.S.T. Goncalves, Bioorg. Med. Chem. 16 (2008) 3274-3282
37. (b) K.I.E. McLuckie, Z.A.E. Waller, D.A. Sanders, D. Alves, R. Rodriguez, J. Dash, G.J. McKenzie, A.R. Venkitaraman, S. Bolsubramanian, J. Am. Chem. Soc. 133 (2011) 2658-2663
38. K.-Y. Chu, J. Griffiths, J. Chem. Soc. Perkin Trans. 1 (1978) 1083-1087.
39. (a) C.G. Pierpont, Coord. Chem. Rev. 216- 217 (2001) 99-125
40. (b) C.G. Pierpont, C.W. Lange, Inorg. Chem. 41 (1994) 381-492
41. (a) J. Gaultier, C. Hauw, Acta Crystallogr. 19 (1965) 585-590
42. A.E. Shvets, A.J. Malmanis, Ya.F. Freimanis, Ya.Ya. Bleidelis, J.F. Dregeris, Zh. Strukt. Khim. 20 (1979) 414-419
43. V. Bertolasi, P. Gilli, V. Ferretti, G. Gilli, Acta Crystallogr. Sec. B: Struct. Sci. 51 (1995) 1004-1015
44. A.E. Shvets, Ya.Ya. Bleidelis, Ya.F. Freimanis, Zh. Strukt. Khim. 16 (1975) 640-644
45. D.E. Lynch, I. McClenaghan, Acta Crystallogr. E 57 (2001) o287-0288 (Acta Crystallogr. C: Cryst. Struct. Commun. 56 (2000) e537.
46. Acta Crystallogr., Sec. C: Cryst. Struct. Commun. 56 (2000) e588.
47. Acta Crystallogr., Sec. E: Struct. Rep. Online 59 (2003) o1427)
48. F.-L. Yang, T. Win, S. Bittner, Z. Kristallogr, New Cryst. Struct. 220 (2005) 173
49. Y. Brandy, R.J. Butcher, T.A. Adesiyun, S. Berhe, O. Bakare, Acta Crystallogr. Sec. E: Struct. Rep. Online 65 (2009) o64.
50. G.R. Desiraju, J.J. Vittal, A. Ramanan, Crystal Engineering, World Scientific Publishing Co. Pvt. Ltd., 2011.
51. A. Bolognese, G. Correale, M. Manfra, A. Lavecchia, E. Novellino, S. Pepe, J. Med. Chem. 49 (2006) 5110-5118.
52. A. Bolognese, G. Correale, M. Manfra, A. Lavecchia, O. Mazzoni, E. Novellino, V. Barone, A. Pani, E. Tramontano, P. La Colla, C. Murgioni, I. Serra, G. Setzu, R. Loddo, J. Med. Chem. 45 (2001) 5205-5216. 3)