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Synthesis 2014; 46(20): 2771-2779
DOI: 10.1055/s-0034-1378345
DOI: 10.1055/s-0034-1378345
paper
Improved Syntheses of Benzyl Hydraphile Synthetic Cation-Conducting Channels
Weitere Informationen
Publikationsverlauf
Received: 08. April 2014
Accepted after revision: 29. Mai 2014
Publikationsdatum:
30. Juli 2014 (online)
Abstract
The tris(macrocycle)s that function in bilayer membranes as ion channels have recently shown versatile new applications such as antibiotic synergists and as agents for direct injection chemotherapy. This report records the development of new and versatile approaches to these molecules that produce significantly better overall yields for a group of previously reported hydraphiles having spacer chains ranging from octylene to hexadecylene.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1 Tabushi I, Kuroda Y, Yokota K. Tetrahedron Lett. 1982; 23: 4601
- 2 Jullien L, Lehn J.-M. Tetrahedron Lett. 1988; 29: 3803
- 3 Carmichael VE, Dutton PJ, Fyles TM, James TD, Swan JA, Zojaji M. J. Am. Chem. Soc. 1989; 111: 767
- 4 Nakano A, Xie Q, Mallen JV, Echegoyen L, Gokel GW. J. Am. Chem. Soc. 1990; 112: 1287
- 5a Gokel GW, Dishong DM, Diamond CJ. J. Chem. Soc., Chem. Commun. 1980; 1053
- 5b Gokel GW, Echegoyen L In Advances in Bio-organic Frontiers . Vol. 1. Dugas H. Springer; Berlin: 1990: 116-141
- 6a Murillo O, Watanabe S, Nakano A, Gokel GW. J. Am. Chem. Soc. 1995; 117: 7665
- 6b Fyles TM, Van Straaten-Nijenhuis WF. Comprehensive Supramolecular Chemistry . Vol. 10. Reinhoudt DN. Pergamon; Oxford: 1996: 53-77
- 6c Gokel GW, Carasel IA. Chem. Soc. Rev. 2007; 36: 378
- 6d Matile S, Vargas Jentzsch A, Montenegro J, Fin A. Chem. Soc. Rev. 2011; 40: 2453
- 6e Chui JK, Fyles TM. Chem. Soc. Rev. 2012; 41: 148
- 7 Gokel GW, Daschbach MM. Coord. Chem. Rev. 2008; 252: 886
- 8 Weber ME, Wang W, Steinhardt SE, Gokel MR, Leevy WM, Gokel GW. New J. Chem. 2006; 30: 177
- 9 Atkins JL, Patel MB, Cusumano Z, Gokel GW. Chem. Commun. 2010; 46: 8166
- 10a Smith BA, Daschbach MM, Gammon ST, Xiao S, Chapman SE, Hudson C, Suckow M, Piwnica-Worms D, Gokel GW, Leevy WM. Chem. Commun. 2011; 47: 7977
- 10b Smith BA, Gammon ST, Xiao S, Wang W, Chapman S, McDermott R, Suckow MA, Johnson JR, Piwnica-Worms D, Gokel GW, Smith BD, Leevy WM. Mol. Pharm. 2011; 8: 583
- 11 Zusi FC, Marathe SA, Tramposch KM. US Patent 4731382, 1988
- 12 Hill JW, Carothers WH. J. Am. Chem. Soc. 1933; 55: 5023
- 13 de Mendoza J.; Cuevas F.; Prados P. personal communication.
- 14 de Mendoza J, Cuevas F, Prados P, Meadows ES, Gokel GW. Angew. Chem. Int. Ed. 1998; 37: 1534
- 15 Gatto VJ, Miller SR, Gokel GW. Org. Synth. 1989; 68: 227
- 16 Gokel GW. Chem. Commun. 2000; 1
- 17 Weber ME, Schlesinger PH, Gokel GW. J. Am. Chem. Soc. 2005; 126: 636
- 18 Wang W, Yamnitz CR, Gokel GW. Heterocycles 2007; 73: 825
- 19 Murray CL, Gokel GW. J. Supramol. Chem. 2001; 1: 23
- 20 Keller M, Teng S, Bernhardt G, Buschauer A. ChemMedChem 2009; 4: 1733
- 21 Kotzyba-Hibert F, Lehn JM, Vierling P. Tetrahedron Lett. 1980; 21: 941
- 22 Iso Y, Shindo H, Hamana H. Tetrahedron 2000; 56: 5353
- 23 Cardinale G, Laan JA. M, Van Der Steen D, Ward JP. Tetrahedron 1985; 41: 6051
- 25 Taffa D, Kathiresan M, Walder L. Langmuir 2009; 25: 5371
- 26a Yuen AK. L, Heinroth F, Ward AJ, Masters AF, Maschmeyer T. Microporous Mesoporous Mater. 2012; 148: 62
- 26b Chuit P, Hausser J. Helv. Chim. Acta 1929; 12: 850
- 27 Zhang X.-X, Prata CA. H, Berlin JA, McIntosh TJ, Barthelemy P, Grinstaff MW. Bioconjugate Chem. 2011; 22: 690