Convenient synthesis of 5-aryl(alkyl)sulfanyl-1,10-phenanthrolines from 5,6-epoxy-5,6-dihydro-1,10-phenanthroline, and their activity towards fungal β-d-glycosidases

Tetrahedron

Volumn 67, Issue 39, 2011, Pages 7470-7478

  Dotsenko, Irina A ^a   Curtis, Matthew ^a   Samoshina, Nataliya M ^a   Samoshin, Vyacheslav V ^a  

^a UNIVERSITY OF THE PACIFIC   (United States)

Author keywords

1,10 Phenanthroline; Base induced aromatization; Epoxide deoxygenation; Glycosidase activators inhibitors

Indexed keywords

1,10 PHENANTHROLINE; 5,6 EPOXY 5,6 DIHYDRO 1,10 PHENANTHROLINE; BASE; BETA DEXTRO GLYCOSIDASE; GALACTOSIDASE; GLYCOSIDASE; LIGAND; SULFANYL 1,10 PHENANTHROLINE DERIVATIVE; THIOL; UNCLASSIFIED DRUG;

ARTICLE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; FUNGUS; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 80052030186     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.058     Document Type: Article

References (31)

1. A. Bencini, and V. Lippolis Coord. Chem. Rev. 254 2010 2096 2180
2. C.R. Luman, and F.N. Castellano J.A.M. McCleverty, J. Thomas, Phenanthroline Ligands Compr. Coord. Chem. II vol. 1 2004 Elsevier Oxford, UK 25 39
3. G. Chelucci, and R.P. Thummel Chem. Rev. 102 2002 3129 3170
4. E. Schoffers Eur. J. Org. Chem. 2003 1145 1152
5. Y. Shen, and B.P. Sullivan Inorg. Chem. 34 1995 6235 6236
6. J.M. Mathis, and A.J. Pallenberg Synth. Commun. 27 1997 2943 2951
7. C.R. Brodie, and J.R. Aldrich-Wright Eur. J. Inorg. Chem. 2007 4781 4793
8. S.J. Yousouf, C.R. Brodie, N.J. Wheate, and J.R. Aldrich-Wright Polyhedron 26 2007 318 328
9. S. Rabaca, M.C. Duarte, I.C. Santos, L.C.J. Pereira, M. Fourmigue, R.T. Henriques, and M. Almeida Polyhedron 27 2008 1999 2006
10. B. Chesneau, A. Passelande, and P. Hudhomme Org. Lett. 11 2009 649 652
11. S. Krishnan, D.G. Kuhn, and G.A. Hamilton J. Am. Chem. Soc. 99 1977 8121 8123
12. C.J. Moody, C.W. Rees, and R. Thomas Tetrahedron 48 1992 3589 3602
13. E. Schoffers, S.D. Tran, and K. Mace Heterocycles 60 2003 769 772
14. B.H. Northrop, Y.-R. Zheng, K.-W. Chi, and P.J. Stang Acc. Chem. Res. 42 2009 1554 1563
15. A.G. Montalban, A.J. Herrera, and J. Johannsen Tetrahedron Lett. 51 2010 2917 2919
16. R.E. Eibeck Inorg. Synth. 7 1963 128 131
17. M. Sander Chem. Rev. 66 1966 297 339
18. R.C. Larock Synthetic Organic Methodology: Comprehensive Organic Transformations. A Guide to Functional Group Preparations 1989 VCH NY
19. P.E. Sonnet Tetrahedron 36 1980 557 604
20. Y. Mikami, A. Noujima, T. Mitsudome, T. Mizugaki, K. Jitsukawa, and K. Kaneda Tetrahedron Lett. 51 2010 5466 5468
21. M.C. Aversa, A. Barattucci, and P. Bonaccorsi Tetrahedron 64 2008 7659 7683
22. F. Castaneda, A. Burse, W. Boland, and R.K.H. Kinne Int. J. Med. Sci. 4 2007 131 139
23. E.S.H. El Ashry, N. Rashed, and A.H.S. Shobier Pharmazie 55 2000 251 262
24. H. Driguez Top. Curr. Chem. 187 1997 85 116
25. N.S. Tan, B. Brazdova, N.M. Samoshina, and V.V. Samoshin J. Undergrad. Chem. Res. 6 2007 186 192
26. B. Brazdova, N.S. Tan, N.M. Samoshina, and V.V. Samoshin Carbohydr. Res. 344 2009 311 321
27. H.C. Kang, and S.H. Lee Phytochemistry 58 2001 213 219
28. R.G. Guven, A. Kaplan, K. Guven, F. Matpan, and M. Dogru Biotechnol. Bioprocess Eng. 16 2011 114 119
29. S.K. Shankar, S.K. Dhananjay, and V.H. Mulimani Appl. Biochem. Biotechnol. 152 2009 275 285
30. T. Bhowmik, and E.H. Marth Appl. Microbiol. Biotechnol. 33 1990 317 323
31. A.R. Prasad, H.K.L. Tandon, and S.M. Dutta Indian J. Dairy Sci. 55 2002 241 243