Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 16, 2011, Pages 4720-4723

  Daly, Seth ^a   Hayden, Kathryn ^a   Malik, Indranil ^a   Porch, Nikki ^a   Tang, Hong ^a   Rogelj, Snezna ^a   Frolova, Liliya V ^a   Lepthien, Katrina ^a   Kornienko, Alexander ^a   Magedov, Igor V ^a  

^a NEW MEXICO INSTITUTE OF MINING AND TECHNOLOGY   (United States)

Author keywords

Arylation; Indole; Low level VRE; MRSA

Indexed keywords

DIAZONIUM COMPOUND; INDOLE DERIVATIVE; OXYGEN; PENICILLIN G; SULFUR; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; ARYLATION; CHEMICAL REACTION; DRUG METABOLISM; DRUG POTENTIATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; DIAZONIUM COMPOUNDS; FUNGI; INDOLES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; SALTS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS;

EID: 79960914390     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.06.081     Document Type: Article

References (24)

1. S. Pichereau, and W.E. Rose Expert Opin. Pharmacother. 11 2010 3009
2. E. Tacconelli, and M.A. Cataldo Int. J. Antimicrob. Agents 31 2008 99
3. Y. Kobayashi, M. Ichioka, T. Hirose, K. Nagai, A. Matsumoto, H. Matsui, H. Hanaki, R. Masuma, Y. Takahashi, S. Omura, and T. Sunazuka Bioorg. Med. Chem. Lett. 20 2010 6116
4. A.M.L. Hossion, N. Otsuka, R.K. Kandahary, T. Tsuchiya, W. Ogawa, A. Iwado, Y. Zamami, and K. Sasaki Bioorg. Med. Chem. Lett. 20 2010 5349
5. L. Hu, M.L. Kully, D.W. Boykin, and N. Abood Bioorg. Med. Chem. Lett. 19 2009 4626
6. B.C. Dixit, H.M. Patel, and D.J. Desai J. Serb. Chem. Soc. 72 2007 119
7. A.A. Jarrahpour, M. Motamedifar, K. Pakshir, N. Hadi, and M. Zarei Molecules 9 2004 815
8. A. Ozturk, and M.I. Abdullah Sci. Total Environ. 358 2006 137
9. K.C. Joshi, V.N. Pathak, P. Arya, and P. Chand Agric. Biol. Chem. 43 1979 171
10. N. Srivastava, and A.K. Sengupta Indian J. Chem. 22B 1983 707
11. A.H. Jackson, N. Prasitpan, P.V.R. Shannon, and A.C. Tinker J. Chem. Soc., Perkin Trans. 1 1987 2543
12. M.P. Doyle, J.F. Dellaria, B. Siegfried, and S.W. Bishop J. Org. Chem. 42 1977 3494
13. C. Molinaro, J. Mowat, F. Gosselin, P.D. O'Shea, J.-F. Marcoux, R. Angelaud, and I.W. Davies J. Org. Chem. 72 2007 1856
14. S. Raucher, and G.A. Koolpe J. Org. Chem. 48 1983 2066
15. N.P. Grimster, C. Gauntlett, C.R.A. Godfrey, and M.J. Gaunt Angew. Chem. Int. Ed. 44 2005 3125
16. As our work was in progress, a similar synthesis of carbazoles, utilizing the sequential Heck/electrocyclization process, appeared in the literature: M. Hussain, D.T. Tung, and P. Langer Synlett 2009 1822
17. G. De Martino, M.C. Edler, G. La Regina, A. Coluccia, M.C. Barbera, D. Barrow, R.I. Nicholson, G. Chiosis, A. Brancale, E. Hamel, M. Artico, and R. Silvestri J. Med. Chem. 49 2006 947
18. H. Inion, H. De Vogelaer, M. Descamps, J. Bauthier, M. Colot, J. Richard, and R. Charlier Eur. J. Med. Chem. 12 1977 483
19. B.A. Forbes, D.F. Sahm, and A.S. Weissfeld Bailey & Scott's Diagnostic Microbiology, 10th ed 1998 Mosby St. Louis
20. B.D. Jett, K.L. Hatter, M.M. Huycke, and M.S. Gilmore Biotechniques 23 1997 648
21. Subcommittee on Antifungal Susceptibility Testing (AFST) of the ESCMID European Committee for Antimicrobial Susceptibility Testing (EUCAST) Clin. Microbiol. Infect. 14 2008 398
22. M. Mohtar, S.A. Johari, A.R. Li, M.M. Isa, S. Mustafa, A.M. Ali, and D.F. Basri Curr. Microbiol. 59 2009 181
23. N.M. Evdokimov, S. Van slambrouck, P. Heffeter, L. Tu, B. Le Clave, D. Lamoral-Theys, C.J. Hooten, P.Y. Uglinskii, S. Rogelji, R. Kiss, W.F.A. Steelant, W. Berger, J.J. Yang, C.J. Bologa, A. Kornienko, and I.V. Magedov J. Med. Chem. 54 2011 2012
24. W.H. Dekker, H.A. Selling, and J.C. Overeem J. Agric. Food Chem. 23 1975 785