Synthesis of the first morpholine-containing iron(II) clathrochelates: A new class of efficient functionalized transcription inhibitors

Inorganica Chimica Acta

Volumn 421, Issue , 2014, Pages 300-306

  Belov, Alexander S ^a   Vologzhanina, Anna V ^a   Novikov, Valentin V ^a   Negrutska, Valentina V ^b   Dubey, Igor Y ^b   Mikhailova, Zoya A ^a   Lebed, Ekaterina G ^a   Voloshin, Yan Z ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b INSTITUTE OF MOLECULAR BIOLOGY AND GENETICS   (Ukraine)

Author keywords

Clathrochelates; Drug design; Iron complexes; Macrocyclic compounds; RNA polymerase; Transcription inhibitors

Indexed keywords

NUCLEOPHILES; RNA;

CLATHROCHELATES; DRUG DESIGN; IRON COMPLEX; MACROCYCLIC COMPOUNDS; RNA POLYMERASE;

IRON COMPOUNDS;

EID: 84904359770     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2014.06.016     Document Type: Article

References (57)

1. Y. Voloshin, O. Varzatskii, S. Shul'ga, V. Novikov, A. Belov, I. Makarenko, I. Dubey, D. Krivorotenko, V. Negrutska, K. Zhizhin, N. Kuznetsov, Y. Bubnov, in: Proceed. 10th EUROBIC, 2010, pp. 29-38.
2. V.V. Novikov, O.A. Varzatskii, V.V. Negrutska, Y.N. Bubnov, L.G. Palchykovska, I.Y. Dubey, and Y.Z. Voloshin J. Inorg. Biochem. 124 2013 42
3. O.A. Varzatskii, V.V. Novikov, S.V. Shulga, A.S. Belov, A.V. Vologzhanina, V.V. Negrutska, I.Y. Dubey, Y.N. Bubnov, and Y.Z. Voloshin Chem. Commun. 50 2014 3166
4. Y.Z. Voloshin, N.A. Kostromina, and R. Kraemer Clathrochelates: Synthesis Structure and Properties 2002 Elsevier Amsterdam
5. V.A. Pal'chikov Russ. J. Org. Chem. 49 2013 787
6. R.P.K. Babu, and S.N. Maiti Heterocycles 69 2006 539
7. W. Xu, D.L. Gray, S.A. Glase, and N.S. Barta Bioorg. Med. Chem. Lett. 18 2008 5550
8. D.J. O'Neill, A. Adedoyin, J.A. Bray, D.C. Deecher, A. Fensome, J.A. Goldberg, J. Harrison, L. Leventhal, C. Mann, L. Mark, L. Nogle, N.R. Sullivan, T.B. Spangler, E.A. Terefenko, E.J. Trybulski, A.J. Uveges, A. Vu, G.T. Whiteside, and P. Zhang J. Med. Chem. 54 2011 6824
9. P.A. Burland, H.M.I. Osborn, and A. Turkson Bioorg. Med. Chem. 19 2011 5679
10. Q. Chao, K.G. Sprankle, R.M. Grotzfeld, A.G. Lai, T.A. Carter, A.M. Velasco, R.N. Gunawardane, M.D. Cramer, M.F. Gardner, J. James, P.P. Zarrinkar, H.K. Patel, and S.S. Bhagwat J. Med. Chem. 52 2009 7808
11. J.C. Verheijen, K. Yu, L. Toral-Barza, I. Hollander, and A. Zask Bioorg. Med. Chem. Lett. 20 2010 375
12. S.H. Yang, D.B. Khadka, S.H. Cho, H.-K. Ju, K.Y. Lee, H.J. Han, K.-T. Lee, and W.-J. Cho Bioorg. Med. Chem. 19 2011 968
13. J. Wang, X. Wang, Y. Chen, S. Chen, G. Chen, L. Tong, L. Meng, Y. Xie, J. Ding, and C. Yang Bioorg. Med. Chem. Lett. 22 2012 339
14. B.Z. Lu, G. Li, S. Rodriguez, J. Liu, M.C. Eriksson, Z. Tan, J.J. Song, N.K. Yee, V. Farina, and C.H. Senanayake Synlett 24 2013 317
15. M.K. Ameriks, H. Cai, J.P. Edwards, D. Gebauer, E. Gleason, Y. Gu, L. Karlsson, S. Nguyen, S. Sun, R.L. Thurmond, and J. Zhu Bioorg. Med. Chem. Lett. 19 2009 6135
16. Z.-L. You, D.-M. Xian, M. Zhang, X.-S. Cheng, and X.-F. Li Bioorg. Med. Chem. 20 2012 4889
17. J.M. Wisniewska, C.B. Rödl, A.S. Kahnt, E. Buscató, S. Ulrich, Y. Tanrikulu, J. Achenbach, F. Rörsch, S. Grösch, G. Schneider, J. Cinatl, E. Proschak, D. Steinhilber, and B. Hofmann Biochem. Pharmacol. 83 2012 228
18. R. Zindell, D. Riether, T. Bosanac, A. Berry, M.J. Gemkow, A. Ebneth, S. Löbbe, E.L. Raymond, D. Thome, D.-T. Shih, and D. Thomson Bioorg. Med. Chem. Lett. 19 2009 1604
19. G.M.P. Giblin, A. Billinton, M. Briggs, A.J. Brown, I.P. Chessell, N.M. Clayton, A.J. Eatherton, P. Goldsmith, C. Haslam, M.R. Johnson, W.L. Mitchell, A. Naylor, A. Perboni, B.P. Slingsby, and A.W. Wilson J. Med. Chem. 52 2009 5785
20. J.-L. Peglion, C. Poitevin, C.M. La Cour, D. Dupuis, and M.J. Millan Bioorg. Med. Chem. Lett. 19 2009 2133
21. S. Gangula, C.R. Elati, S.V. Mudunuru, A. Nardela, A. Dongamanti, A. Bhattacharya, and R. Bandichhor Synth. Commun. 40 2010 2254
22. J. Keldenich, C. Michon, A. Nowicki, and F. Agbossou-Niedercorn Synlett 20 2011 2939
23. T.-X. Meìtro, A. Cochi, D.G. Pardo, and J. Cossy J. Org. Chem. 76 2011 2594
24. R.A. Ancliff, C.M. Cook, C.D. Eldred, P.M. Gore, L.A. Harrison, M.A. Hayes, S.T. Hodgson, D.B. Judd, S.E. Keeling, X.Q. Lewell, G. Mills, G.M. Robertson, S. Swanson, A.J. Walker, M. Wilkinson, Int. Patent Appl. no. WO 2003 082 861, 2003; Chem. Abstr., 139 (2003) 307 777.
25. I. Hermecz, A. Santa-Csutor, C. Gonczi, G. Heja, E. Csikos, K. Simon, A. Smelko-Esek, and B. Podanyi Pure Appl. Chem. 73 2001 1401
26. J.L. Dnaz, R. Cuberes, J. Berrocal, M. Contijoch, U. Christmann, A. Fernández, A. Port, J. Holenz, H. Buschmann, C. Laggner, M.T. Serafini, J. Burgueso, D. Zamanillo, M. Merlos, J.M. Vela, and C. Almansa J. Med. Chem. 55 2012 8211
27. R.J. Lukas, A.Z. Muresan, M.I. Damaj, B.E. Blough, X. Huang, H.A. Navarro, S.W. Mascarella, J.B. Eaton, S.K. Marxer-Miller, and F.I. Carroll J. Med. Chem. 53 2010 4731
28. F.I. Carroll, A.Z. Muresan, B.E. Blough, H.A. Navarro, S.W. Mascarella, J.B. Eaton, X. Huang, M.I. Damaj, and R.J. Lukas J. Med. Chem. 54 2011 1441
29. Y. Tamura, N. Omori, N. Kouyama, Y. Nishiura, K. Hayashi, K. Watanabe, Y. Tanaka, T. Chiba, H. Yukioka, H. Sato, and T. Okuno Bioorg. Med. Chem. Lett. 22 2012 6554
30. A.D. Borthwick, J. Liddle, D.E. Davies, A.M. Exall, C. Hamlett, D.M. Hickey, A.M. Mason, I.E.D. Smith, F. Nerozzi, S. Peace, D. Pollard, S.L. Sollis, M.J. Allen, P.M. Woollard, M.A. Pullen, T.D. Westfall, and D.J. Stanislaus J. Med. Chem. 55 2012 783
31. S.B. Ravula, J. Yu, J.A. Tran, M. Arellano, F.C. Tucci, W.J. Moree, B.-F. Li, R.E. Petroski, J. Wen, S. Malany, S.R.J. Hoare, A. Madan, P.D. Crowe, and G. Beaton Bioorg. Med. Chem. Lett. 22 2012 421
32. A.U. Rao, N. Shao, R.G. Aslanian, T.-Y. Chan, S.J. Degrado, L. Wang, B. McKittrick, M. Senior, R.E. West, S.M. Williams, R.-L. Wu, J. Hwa, B. Patel, S. Zheng, C. Sondey, and A. Palani ACS Med. Chem. Lett. 3 2012 198
33. S. Sangthong, K. Krusong, N. Ngamrojanavanich, T. Vilaivan, S. Puthong, S. Chandchawan, and N. Muangsin Bioorg. Med. Chem. Lett. 21 2011 4813
34. U. Soumyanarayanan, V.G. Bhat, S.S. Kar, and J.A. Mathew Org. Med. Chem. Lett. 2 2012 23
35. M.O. Shibinskaya, S.A. Lyakhov, A.V. Mazepa, S.A. Andronati, A.V. Turov, N.M. Zholobak, and N.Y. Spivak Eur. J. Med. Chem. 45 2010 1237
36. K. Kamisski, J. Obniska, B. Wiklik, and D. Atamanyuk Eur. J. Med. Chem. 46 2011 4634
37. Nithinchandra, B. Kalluraya, S. Aamir, and A.R. Shabaraya Eur. J. Med. Chem. 54 2012 597
38. G. Ponzio, and F. Baldrocco Gazz. Chim. Ital. 60 1930 415
39. Y.Z. Voloshin, V.E. Zavodnik, O.A. Varzatskii, V.K. Belsky, A.V. Palchik, N.G. Strizhakova, I.I. Vorontsov, and M.Y. Antipin Dalton Trans. 2002 1193
40. O. Trott, and A.J. Olson J. Comput. Chem. 31 2010 455
41. M.F. Sanner J. Mol. Graph. Model. 17 1999 57
42. L.L.C. Schrodinger, The PyMOL Molecular Graphics System, Version 1.3r1 2010.
43. E.H. Kerns, and L. Di Drug-like Properties: Concepts, Structure Design and Methods 2008 Elsevier Amsterdam
44. M. Kansy, F. Senner, and K. Gubernator J. Med. Chem. 41 1998 1007
45. E.T. Schenborn, and R.C. Mierendorf Nucleic Acids Res. 13 1985 6223
46. L.G. Palchykovska, I.V. Alexeeva, V.G. Kostina, M.O. Platonov, V.V. Nehrutska, O.M. Deriabin, O.A. Tarasov, and A.D. Shved Ukr. Biokhim. Zh. 80 2008 140
47. L.G. Palchykovska, I.V. Alexeeva, V.V. Negrutska, Yu.K. Kostyuk, T.M. Indychenko, O.M. Kostenko, D.V. Kryvorotenko, A.D. Shved, and I. Ya Biopolym. Cell 26 2010 508
48. G.M. Sheldrick sadabs v. 2.01, Bruker/Siemens Area Detector Absorption Correction Program 1998 Bruker AXS Madison, Wisconsin, USA
49. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112
50. S.K. Wolff, D.J. Grimwood, J.J. McKinnon, M.J. Turner, D. Jayatilaka, and M.A. Spackman CrystalExplorer (Version 3.0) 2012 University of Western Australia
51. Y.Z. Voloshin, V.E. Zavodnik, O.A. Varzatskii, V.K. Belsky, I.I. Vorontsov, and M.Y. Antipin Inorg. Chim. Acta 321 2001 116
52. Y.Z. Voloshin, O.A. Varzatskii, A.V. Palchik, I.I. Vorontsov, M.Y. Antipin, and E.G. Lebed Inorg. Chim. Acta 358 2005 131
53. I.G. Belaya, G.E. Zelinskii, A.S. Belov, O.A. Varzatskii, V.V. Novikov, A.V. Dolganov, H. Kozlowski, Ł. Szyrwiel, Y.N. Bubnov, and Y.Z. Voloshin Polyhedron 40 2012 32
54. A.B. Burdukov, M.A. Vershinin, N.V. Pervukhina, Y.Z. Voloshin, and O.A. Varzatskii Russ. Chem. Bull. 55 2006 1982
55. A.B. Burdukov, E.G. Boguslavskii, V.A. Reznikov, N.V. Pervukhina, M.A. Vershinin, Y.Z. Voloshin, O.A. Varzatskii, and Y.N. Bubnov Russ. Chem. Bull. 54 2005 1125
56. J.J. McKinnon, F.P.A. Fabbiani, and M.A. Spackman Cryst. Growth Des. 7 2007 755
57. J.J. McKinnon, D. Jayatilaka, and M.A. Spackman Chem. Commun. 2007 3814