Compounds Based on a Triethyl- or Trimethoxybenzene Scaffold Bearing Pyrazole, Pyridine, and Pyrimidine Groups: Syntheses and Representative Binding Studies towards Carbohydrates

Abstract

Pyrazole-based artificial receptors have often been used in the recognition of ions, but in the area of sugar recognition the potential of pyrazole-based recognition groups has only been rarely examined. In this paper we describe the syntheses of twelve new pyrazole-bearing compounds, which are all potentially applicable for use as carbohydrate receptors. The prepared compounds enforce tripodal architecture and are based on a triethyl- or trimethoxybenzene scaffold. Representative complexation studies with selected carbohydrates showed interesting binding preferences of the new compounds.

Key words

tripodal receptors - pyrazole groups - carbohydrate recognition - triethylbenzene scaffold - trimethoxybenzene scaffold

• References


For examples of reviews on carbohydrate recognition with artificial receptors using noncovalent interactions, see:
• 1a Davis AP, Wareham RS. Angew. Chem. Int. Ed. 1999; 38: 2979
• 1b Mazik M. ChemBioChem 2008; 9: 1015
• 1c Walker DB, Joshi G, Davis AP. Cell. Mol. Life Sci. 2009; 66: 3177
• 1d Mazik M. Chem. Soc. Rev. 2009; 38: 935
• 1e Davis AP. Org. Biomol. Chem. 2009; 7: 3629
• 1f Kubik S. Angew. Chem. Int. Ed. 2009; 48: 1722
• 1g Mazik M. RSC Adv. 2012; 2: 2630

For examples of reviews on boronic acid-based receptors, see:
• 2a James TD, Phillips MD, Shinkai S. Boronic Acids in Saccharide Recognition . Royal Society of Chemistry; Cambridge: 2006
• 2b Boronic Acids. Preparation and Applications in Organic Synthesis and Medicine. Hall DG. Wiley-VCH; Weinheim: 2005
• 2c James TD, Shinkai S. Top. Curr. Chem. 2002; 218: 159
• 2d James TD, Sandanayake KR. A. S, Shinkai S. Angew. Chem., Int. Ed. Engl. 1996; 35: 1910
• 3a Gabius HJ. The Sugar Code – Fundamentals of Glycoscience . Wiley-Blackwell; Weinheim: 2009
• 3b Gabius H.-J, André S, Jiménez-Barbero J, Romero A, Solis D. Trends Biochem. Sci. 2011; 36: 298
• 3c Lis H, Sharon N. Lectins . Kluwer Academic Publishers; Dordrecht: 2003
• 3d Lis H, Sharon N. Chem. Rev. 1998; 98: 637
• 3e Quiocho FA. Pure Appl. Chem. 1989; 61: 1293
• 3f Weiss WI, Drickamer K. Annu. Rev. Biochem. 1996; 65: 441
• 4a Mazik M, Hartmann A. Beilstein J. Org. Chem. 2010; 6: No. 9
• 4b Mazik M, Kuschel M. Chem. Eur. J. 2008; 14: 2405
• 4c Rosien J.-R, Seichter W, Mazik M. Org. Biomol. Chem. 2013; 11: 6569
• 4d Koch N, Rosien J.-R, Mazik M. Tetrahedron 2014; 70: 8758
• 4e For an example of benzimidazole-bearing carbohydrate receptor, see: Mazik M, Cavga H. J. Org. Chem. 2007; 72: 831
• 5 For examples of carbohydrate receptors bearing pyrazole groups, see ref. 4d and: Sonnenberg C, Hartmann A, Mazik M. Nat. Prod. Commun. 2012; 7: 321
• 6 Lippe J, Mazik M. J. Org. Chem. 2015; 80: 1427
• 7a Lippe J, Seichter W, Mazik M. Org. Biomol. Chem. 2015; 13: 11622
• 7b Mazik M, Cavga H, Jones PG. J. Am. Chem. Soc. 2005; 127: 9045
• 7c Mazik M, Radunz W, Boese R. J. Org. Chem. 2004; 69: 7448
• 7d Mazik M, Radunz W, Sicking W. Org. Lett. 2002; 4: 4579
• 7e Mazik M, Sicking W. Tetrahedron Lett. 2004; 45: 3117

For examples, see:
• 8a Kuswandi B, Nuriman Verboom W, Reinhoudt DN. Sensors 2006; 6: 978
• 8b Chin J, Walsdorff C, Stranix B, Oh J, Chung HJ, Park S.-M, Kim K. Angew. Chem. Int. Ed. 1999; 38: 2756
• 8c Chin J, Oh SY, Park SH, Walsdorff C, Stranix B, Ghoussoub A, Lee SJ, Chung HJ, Park S.-M, Kim K. J. Am. Chem. Soc. 2002; 124: 5374
• 8d Hartshorn CM, Steel PJ. Chem. Commun. 1997; 541
• 8e Arunachalam M, Ahamed BN, Ghosh P. Org. Lett. 2010; 12: 2742
• 8f Koch N, Seichter W, Mazik M. Tetrahedron 2015; 71: 8965

For examples of benzene-based receptors bearing different recognition groups, such as phenanthroline, naphthyridine, quinoline, pyridine, pyrimidine, pyridinium, quinolinium, or oxime groups, see:
• 9a Geffert C, Mazik M. J. Org. Chem. 2013; 78: 292
• 9b Mazik M, Geffert C. Org. Biomol. Chem. 2011; 9: 2319
• 9c Mazik M, Sonnenberg C. J. Org. Chem. 2010; 75: 6416
• 9d Mazik M, Hartmann A, Jones PG. Chem. Eur. J. 2009; 15: 9147
• 9e Mazik M, Hartmann A. J. Org. Chem. 2008; 73: 7444
• 9f Mazik M, Cavga H. Eur. J. Org. Chem. 2007; 3633
• 9g Mazik M, Kuschel M. Eur. J. Org. Chem. 2008; 1517
• 9h Mazik M, Cavga H. J. Org. Chem. 2006; 71: 2957
• 9i Mazik M, Kuschel M, Sicking W. Org. Lett. 2006; 8: 855
• 9j Mazik M, Sicking W. Chem. Eur. J. 2001; 7: 664
• 9k Mazik M, Bandmann H, Sicking W. Angew. Chem. Int. Ed. 2000; 39: 551
• 9l Mazik M, Buthe AC. J. Org. Chem. 2007; 72: 8319
• 9m Mazik M, Buthe AC. Org. Biomol. Chem. 2008; 6: 1558

For examples of carbohydrate receptors consisting of biphenyl-, diphenylmethane- or dimesitylmethane-based scaffold, see ref. 4d and:
• 10a Mazik M, König A. J. Org. Chem. 2006; 71: 7854
• 10b Mazik M, König A. Eur. J. Org. Chem. 2007; 3271
• 10c Mazik M, Buthe AC. Org. Biomol. Chem. 2009; 7: 2063
• 11 For examples of receptors combining both a macrocyclic building block and flexible side-arms as recognition units, see ref. 6 and: Lippe J, Mazik M. J. Org. Chem. 2013; 78: 9013
• 12a Li H, Homan EA, Lampkins AJ, Ghiviriga I, Castellano RK. Org. Lett. 2005; 7: 443
• 12b Koch N, Mazik M. Acta Crystallogr., Sect. E: Struct. Rep. Online 2013; 69: o679
• 12c Koch N, Mazik M. Synthesis 2013; 45: 3341
• 13a Bredereck H, Sell R, Effenberger F. Chem. Ber. 1964; 97: 3407
• 13b Werner A, Sánchez-Migallón A, Fruchier A, Eiguero J, Fernández-Castaño C, Foces-Foces C. Tetrahedron 1995; 51: 4779
• 14 Hynes MJ. J. Chem. Soc., Dalton Trans. 1993; 311
• 15a Frassineti C, Ghelli S, Gans P, Sabatini A, Moruzzi MS, Vacca A. Anal. Biochem. 1995; 231: 374
• 15b Frassineti C, Alderighi L, Gans P, Sabatini A, Vacca A, Ghelli S. Anal. Bioanal. Chem. 2003; 376: 1041
• 16 Besseau F, Graton J, Berthelot M. Chem. Eur. J. 2008; 14: 10656
• 17 For a discussion on hydrogen bond basicity of six-membered aromatic N-heterocycles, see: Berthelot M, Laurence C, Safar M, Bessau F. J. Chem. Soc., Perkin Trans. 2 1998; 283
• 18 For a discussion on amino group acidity in aminopyridines and aminopyrimidines, see: Harris MG, Stewart R. Can. J. Chem. 1977; 55: 3800
• 19a For a recent discussion on the importance of intramolecular hydrogen bonding, see: Castellano RK. Molecules 2014; 19: 15783
• 19b For a recent analysis of the influence of intramolecular hydrogen bonds on the binding abilities of artificial receptors, see: Dolenský B, Konvalinka R, Jakubek M, Král V. J. Mol. Struct. 2013; 1035: 124
• 20 For a discussion on selectivity in supramolecular host-guest complexes, see: Schneider H.-J, Yatsimirsky A. Chem. Soc. Rev. 2008; 37: 263
• 21 Wallce KJ, Hanes R, Anslyn E, Morey J, Kilway K, Siegel J. Synthesis 2005; 2080
• 22 Sheldrick GM. SHELXS-97: Program for Crystal Structure Determination . University of Göttingen; Germany: 1997
• 23 Sheldrick GM. SHELXL-2013: Program for Crystal Structure Refinement . University of Göttingen; Germany: 2013