Improved Syntheses of Benzyl Hydraphile Synthetic Cation-Conducting Channels

Nichole S. Curvey; Sarah E. Luderer; John K. Walker; George W. Gokel

doi:10.1055/s-0034-1378345

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(20): 2771-2779
DOI: 10.1055/s-0034-1378345

paper

Improved Syntheses of Benzyl Hydraphile Synthetic Cation-Conducting Channels

Nichole S. Curvey

^aCenter for Nanoscience, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

^cDepartment of Chemistry & Biochemistry, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

,

Sarah E. Luderer

^aCenter for Nanoscience, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

^bMedicinal Chemistry Group, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

,

John K. Walker

^aCenter for Nanoscience, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

^bMedicinal Chemistry Group, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

,

George W. Gokel*

^aCenter for Nanoscience, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

^bMedicinal Chemistry Group, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

^cDepartment of Chemistry & Biochemistry, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA

^dDepartment of Biology, University of Missouri–St. Louis, 1 University Blvd., St. Louis, MO 63121, USA Fax: +1(314)5165342 eMail: gokelg@umsl.edu

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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.

Key words

acylation - benzylation - macrocycles - reduction - supramolecular chemistry

Volltext

Referenzen

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

24a Manske RH. Org. Synth. 1943; 2: 154
24b Mori K. Tetrahedron 2008; 64: 4060

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

Zusatzmaterial

Supporting Information