PEG-mediated one-pot multicomponent reactions for the efficient synthesis of functionalized dihydropyridines and their functional group dependent DNA cleavage activity

Bioorganic Chemistry

Volumn 48, Issue 1, 2013, Pages 8-15

  Pal, Suman ^a   Singh, Vandana ^a   Das, Prolay ^a   Choudhury, Lokman H ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY PATNA   (India)

Author keywords

Dihydropyridine derivatives; DNA cutting activity; MCRs; PEG; pUC 19

Indexed keywords

5 ETHYL 2,3 DIMETHYL 6 AMINO 1 (4 CHLOROPHENYL) 4 (3 NITROPHENYL) 1,4 DIHYDROPYRIDINE 2,3,5 TRICARBOXYLATE; 5 ETHYL 2,3 DIMETHYL 6 AMINO 4 (3 NITROPHENYL) 1 PHENYL 1,4 DIHYDROPYRIDINE 2,3,5 TRICARBOXYLATE; DIHYDROPYRIDINE DERIVATIVE; DIMETHYL 6 AMINO 1 BENZYL 4 (4 CHLOROPHENYL) 5 CYANO 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 4 (4 BROMOPHENYL) 5 CYANO 1 4 TOLYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 4 (4 BROMOPHENYL) 5 CYANO 1 PHENYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 4 (4 CHLOROPHENYL) 5 CYANO 1 (NAPHTHALEN 2 YL) 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 4 (4 CHLOROPHENYL) 5 CYANO 1 4 TOLYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 5 BENZOYL 4 (3 NITROPHENYL) 1 PHENYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 5 BENZOYL 4 (4 CHLOROPHENYL) 1 4 TOLYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 5 CYANO 1,4 BIS(4 METHOXYPHENYL) 1 4 TOLYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 5 CYANO 1,4 DIPHENYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 5 CYANO 4 (3 NITROPHENYL) 1 4 TOLYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 6 AMINO 5 CYANO 4 (3 NITROPHENYL) 1 PHENYL 1,4 DIHYDROPYRIDINE 2,3 DICARBOXYLATE; MACROGOL; PLASMID DNA; PUC19 PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CONTROLLED STUDY; DNA CLEAVAGE; DNA DETERMINATION; DNA SYNTHESIS; ENZYME ACTIVITY; MULTICOMPONENT REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; RECYCLING; ROOM TEMPERATURE;

DIHYDROPYRIDINES; DNA; DNA CLEAVAGE; PLASMIDS; POLYETHYLENE GLYCOLS;

EID: 84877062493     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2013.03.003     Document Type: Article

References (62)

1. J. Marco-Contelles, R. Leon, C. De Los RÍos, A. Samadi, M. Bartolini, V. Andrisano, O. Huertas, X. Barril, F.J. Luque, M.I. RodrÍguez-Franco, B. López, M.G. López, A.G. GarcÍa, M. Do Carmo Carreiras, and M. Villarroya J. Med. Chem. 52 2009 2724 2732
2. N. Edraki, A.R. Mehdipour, M. Khoshneviszadeh, and R. Miri Drug Discov. Today 14 2009 1058 1066
3. D.J. Triggle, D.D. Langs, and R.A. Janis Med. Res. Rev. 9 1989 123 128
4. M. Kawase, A. Shah, H. Gaveriya, N. Motohashi, H. Sakagami, and A. Varga Bioorg. Med. Chem. 10 2002 1051 1055
5. C. Safak, and R. Simsek Mini-Rev. Med. Chem. 6 2006 747 755
6. R.P. Mason, I.T. Mak, M.W. Trumbore, and P.E. Mason Am. J. Cardiol. 84 1999 16 22
7. R.I. Goncharova, and T.D. Kuzhir Mutat Res. 214 1989 257 265
8. J. Briede, M. Stivrina, B. Vigante, D. Stoldere, and G. Duburs Cell Biochem Funct. 26 2008 238 245
9. A.F.E. Rump, M. Boller, R. Berkels, R. Rösen, U. Fricke, and W. Klaus Gen. Pharmacol. 25 1994 447 450
10. E. Fasani, M. Fagnoni, D. Dondi, and A. Albini J. Org. Chem. 71 2006 2037 2045
11. V. Klusa Drugs Future 20 1995 135 138
12. I.O. Donkor, X. Zhou, J. Schmidt, K.C. Agrawal, and V. Kishore Bioorg. Med. Chem. 6 1998 563 568
13. T. Straub, C. Boesenberg, V. Gekeler, and F. Boege Biochemistry 36 1997 10777 10783
14. A. Hilgeroth Mini-Rev. Med. Chem. 2 2002 235 245
15. A. Hilgeroth, and H. Lilie Eur. J. Med. Chem. 38 2003 495 499
16. X.Q. Zhu, B.J. Zhao, and J.P. Cheng J. Org. Chem. 65 2000 8158 8163
17. X.Q. Zhu, H.Y. Wang, J.S. Wang, and Y.C. Liu J. Org. Chem. 66 2001 344 347
18. S. Gaillard, C. Papamicaël, F. Marsais, G. Dupas, and V. Levacher Synlett 2005 441 444
19. J. Sun, E.-Y. Xia, Q. Wu, and C.-G. Yan Org. Lett. 12 2010 3678 3681
20. S. Pal, L.H. Choudhury, and T. Parvin Synth. Commun. 43 2013 986 992
21. W. Gati, M.M. Rammah, M.B. Rammah, F. Couty, and G. Evano J. Am. Chem. Soc. 134 2012 9078 9081
22. K. Oshima, T. Ohmura, and M. Suginome J. Am. Chem. Soc. 134 2012 3699 3702
23. F.J. Fañanás, T. Arto, A. Mendoza, F. Rodríguez, Org. Lett. 13 (2011) 4184-4187.
24. L.H. Choudhury, and T. Parvin Tetrahedron Report 67 2011 8213 8228
25. S. Pal, L.H. Choudhury, and T. Parvin Mol. Divers. 16 2012 129 143
26. S.L. Jain, S. Singhal, and B. Sain Green Chem. 9 2007 740 741
27. N.M. Smith, C.L. Raston, C.B. Smith, and A.N. Sobolev Green Chem. 9 2007 1185 1190
28. L. Nagarapu, R. Mallepalli, L. Yeramanchi, and R. Bantu Tetrahedron Lett. 52 2011 3401 3404
29. B. Sauvagnat, F. Lamaty, R. Lazaro, and J. Martinez Tetrahedron Lett. 39 1998 821 824
30. G.D. Yadav, and B.G. Motirale Org. Process Res. Dev. 13 2009 341 348
31. T.G. Dickerson, N.N. Reed, and K.D. Janda Chem. Rev. 102 2002 3325 3344
32. S. Zalipsky Bioconjugate Chem. 6 1995 150 165
33. S. Zalipsky Adv. Drug Del. Rev. 16 1995 157 182
34. K. Knop, R. Hoogenboom, D. Fischer, and U.S. Schubert Angew. Chem. Int. Ed. 49 2010 6288 6308
35. T. Straub, C. Boesenberg, V. Gekeler, and F. Boege Biochemistry 36 1997 10777 10783
36. A. Basu, P. Jaisankar, and S.G. Kumar Bioorg. Med. Chem. 20 2012 2498 2505
37. H.K.S. Souza Thermochim. Acta 501 2010 1 7
38. I. Lukes, J. Kotek, P. Vojtisek, and P. Hermann Coord. Chem. Rev. 216 2001 287 312
39. A.H.F. Lee, J. Chen, D.S. Liu, T.Y.C. Leung, A.S.C. Chan, and T.H. Li J. Am. Chem. Soc. 124 2002 13972 13973
40. S.H. Wan, F. Liang, X.Q. Xiong, L. Yang, X.J. Wu, P. Wang, X. Zhou, and C.T. Wu Bioorg. Med. Chem. Lett. 16 2006 2804 2806
41. C.R. Smith, R.B. DePrince, J. Dackor, D. Weigl, J. Griffith, and M. Persmark J. Chromatogr. B 854 2007 121 127
42. R. Kuroda, H. Satoh, M. Shinomiya, T. Watanabe, and M. Otsuka Nucl. Acids Res. 23 1995 1524 1530
43. D.T. Breslin, J.E. Coury, J.R. Anderson, L. McFail-Isom, Y. Kan, L.D. Williams, L.A. Bottomley, and G.B. Schuster J. Am. Chem. Soc. 119 1997 5043 5044
44. F. Gumus, G. Eren, L. Acik, A. Celebi, F. Ozturk, S. YIlmaz, R.I. Sagkan, S. Gur, A. Ozkul, A. ElmalI, and Y. Elerman J. Med. Chem. 52 2009 1345 1357
45. S. Franklin, and J. Curr Opin. Chem. Biol. 5 2001 201 208
46. F.E. Jacobsen, J.A. Lewis, and S.M. Cohen J. Am. Chem. Soc. 128 2006 3156 3157
47. R.A. Moss, K. Bracken, and J. Zhang Chem. Commun. 6 1997 563 564
48. B. Armitage Chem. Rev. 98 1998 1171 1200
49. S.R. Rajski, and R.M. Williams Chem. Rev. 98 1998 2723 2796
50. S. Aoki, and E. Kimura Chem. Rev. 104 2004 769 787
51. Y.-P. Liu, N. Jiang, J. Zhang, X. Wei, H.-H. Lin, and X.-Q. Yu Chem. Biodivers. 3 2006 958 966
52. M. Egli, G. Minasov, V. Tereshko, P.S. Pallan, M. Teplova, G.B. Inamati, E.A. Lesnik, S.R. Owens, B.S. Ross, T.P. Prakash, and M. Manoharan Biochemistry 44 2005 9045 9057
53. K.-W. Bair, R.-L. Tuttle, V.-C. Knick, M. Cory, and D.-D. McKee J. Med. Chem. 33 1990 2385 2393
54. J. Mazerski, and K. Muchewicz Acta Biochim. Pol. 47 2000 65 78
55. Y.-C. Zhao, J. Zhang, Y. Huang, G.-Q. Wang, Yu. Xiao-Qi, and X.-Q. Yu Bioorg. Med. Chem. Lett. 14 2006 4151 4157
56. L.S. Kappen, T.R. Lee, C.-C. Yang, and I.H. Goldberg Biochemistry 28 1989 4540 4542
57. Y.-C. Zhao, J. Zhang, Yu. Huang, G.-Q. Wang, and X.-Q. Yu Bioorg. Med. Chem. Lett. 17 2007 2745 2748
58. G. Pratviel, J. Bernadou, and B. Meunier Angew. Chem. Int. Ed. Engl. 34 1995 746 769
59. V. Dahaoui-Gindrey, C. Lecomte, and R. Guilard Coord. Chem. Rev. 178-180 1998 1313 1405
60. S.-J. Mannino, C.-L. Jenkins, and R.-T. Raines Biochemistry 38 1999 16178 16186
61. V.M. Gonzalez, J.M. Perez, and C. Alonso J. Inorg. Biochem. 68 1997 283 287
62. F. Ozturk, L. Acik, I. Sener, F. Karci, and E. Kilic Turk. J. Chem. 36 2012 293 302