Expeditious Synthesis of Glycosylated Phthalocyanines

Xavier Álvarez-Micó; Mario J. F. Calvete; Michael Hanack; Thomas Ziegler

doi:10.1055/s-2007-983753

PAPER

Expeditious Synthesis of Glycosylated Phthalocyanines

Xavier Álvarez-Micó, Mario J. F. Calvete, Michael Hanack, Thomas Ziegler*
Institute of Organic Chemistry, University of Tuebingen, Auf der Morgenstelle 18, 72076 Tuebingen, Germany
Fax: +49(7071)295244; e-Mail: thomas.ziegler@uni-tuebingen.de;

Abstract

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Abstract

3,4-Dicyanophenyl O- and S-glycosides in the gluco, galacto, lacto, and cellobiose series were prepared in virtually quantitative yield through nucleophilic aromatic substitution of 4-nitrophthalonitrile with acetyl-protected glycoses and 1-thio-glycoses. Similarly, 2-(3,4-dicyanophenoxy)ethyl 2,3,4,6-tetra-O-acetyl-β-d-gluco- and galacto-pyranosides were obtained by nucleophilic substitution of 2-(tosyloxy)ethyl 2,3,4,6-tetra-O-acetyl-β-d-gluco- and -galactopyranoside with 3,4-dicyanophenol in 82% and 94% yields, respectively. All glycosides were deacetylated and tetramerized to the corresponding glycosylated zinc(II) phthalocyanines without further purification using a template condensation in 42-54% yields.

Key words

carbohydrate - phthalocyanine - glycoside - cellular uptake

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References

1a Varki A. Glycobiology 1993, 3: 97

1b Sears P. Wong C.-H. Cell. Mol. Life Sci. 1998, 54: 223

2 Gabius HJ. Gabius S. Glycosciences: Status and Perspectives Chapman & Hall; Weinheim: 1997.

3a Paulson JC. Trends Biochem. Sci. 1989, 14: 272

3b Dwek RA. Chem. Rev. 1996, 96: 683

4a Schmidt RR. Angew. Chem., Int. Ed. Engl. 1986, 25: 212 ; Angew. Chem., 1986, 98, 213

4b Schmidt RR. Kinzy W. Adv. Carbohydr. Chem. Biochem. 1994, 50: 21

4c Schmidt RR. Pure Appl. Chem. 1989, 61: 1257

5 Schmidt RR. Pure Appl. Chem. 1998, 70: 397

6a Kazunoho T. Tatsuta K. Chem. Rev. 1993, 93: 1503

6b Jung K.-H. Müller M. Schmidt RR. Chem. Rev. 2000, 100: 4423

7 Schmidt RR. Modern Methods in Carbohydrate Synthesis Khan SH. O’Neill RA. Harwood Academic Publishers GmbH; Amsterdam: 1996.

8a Berven LA. Dolphin D. Withers SG. Can. J. Chem. 1990, 68: 1859

8b Lindberg B. Acta Chem. Scand. 1950, 4: 49

8c Ferrier RJ. Fortschr. Chem. Forsch. 1970, 14: 389

8d Huchel U. Schmidt C. Schmidt RR. Tetrahedron Lett. 1995, 36: 9457

9 Alvarez-Mico X. Calvete MJF. Hanack M. Ziegler Th. Carbohydrate Res. 2006, 324: 440

10 Kornblum N. Cheng L. Kerber RC. Kestner MM. Newton BN. Pinnick HW. Smith RG. Wade PA. J. Org. Chem. 1976, 41: 1560

11a Rodimann E. Schmidt W. Nischk GE. Makromol. Chem. 1969, 130: 45

11b Mauleon D. Granados R. Minguillon C. J. Org. Chem. 1983, 48: 3105

12 Beck JR. J. Org. Chem. 1972, 37: 3224

13 Knudsen RD. Snyder HR. J. Org. Chem. 1974, 39: 3343

14a Idoux JP. Gupton MT. McCurry CK. Crews AD. Jurss CD. Colon C. Rampi R. J. Org. Chem. 1983, 48: 3771

14b March J. Advanced Organic Chemistry McGraw-Hill; New York: 1977. 2nd Ed..

15a Dini D. Hanack M. The Porphyrin Handbook Vol. 17: Kadish KM. Smith KM. Guilard R. Academic Press; New York: 2003. p.1

15b Cook M. Chambrier I. The Porphyrin Handbook Vol. 17: Kadish KM. Smith KM. Guilard R. Academic Press; New York: 2003. p.37

15c Wöhrle D. Schnurpfeil G. The Porphyrin Handbook Vol. 17: Kadish KM. Smith KM. Guilard R. Academic Press; New York: 2003. p.177

15d Wark M. The Porphyrin Handbook Vol. 17: Kadish KM. Smith KM. Guilard R. Academic Press; New York: 2003. p.247

15e Erk P. Hengelsberg H. The Porphyrin Handbook Vol. 19: Kadish KM. Smith KM. Guilard R. Academic Press; New York: 2003. p.105

15f Bouvet M. The Porphyrin Handbook Vol. 19: Kadish KM. Smith KM. Guilard R. Academic Press; New York: 2003. p.37

16 Ben-Hur E. Chan W.-S. The Porphyrin Handbook Vol. 19: Kadish KM. Smith KM. Guilard R. Academic Press; New York: 2003. p.1 ; and references cited therein

17 Phthalocyanines, Properties and Applications Vols. 1-4: Leznoff CC. Lever ABP. VCH; New York: 1989-1996.

18 van Lier JE. Spikes JD. Photosensitizing Compounds: Their Chemistry, Biology and Clinical Use (CIBA Foundation Symposium 146) Dougherty TJ. Bock G. Harnett S. Wiley; Chichester: 1989. p.17

19 Roeder B. Naether D. Lewald T. Braune M. Nowak C. Freyer W. Biophys. Chem. 1990, 35: 303

20 Komatsu K. Jpn. J. Cancer Res. 1991, 82: 599

21a Maillard P. Guerquin-Kern J.-L. Momenteau M. Gaspard S. J. Am. Chem. Soc. 1989, 111: 9125

21b Lee P. Lo P.-C. Chan E. Fong W.-P. Ko W.-H. Ng D. Tetrahedron Lett. 2005, 46: 1551

21c Ribeiro AO. Tomé JPC. Neves MGPMS. Tomé AC. Cavaleiro JAS. Iammoto Y. Torres T. Tetrahedron Lett. 2006, 47: 9177

22 Alvarez-Mico X. Calvete MJF. Hanack M. Ziegler Th. Tetrahedron Lett. 2006, 47: 3283

23 MacDonald I. Dougherty T. J. Porphyrins Phthalocyanines 2001, 5: 105

24 Camerin M. Rello S. Villanueva A. Ping X. Kenney M. Rodgers M. Jori G. Eur. J. Cancer 2005, 8: 1203

25a Ono N. Bougauchi M. Maruyama K. Tetrahedron Lett. 1992, 33: 1629

25b Maillard P. Guerquin-Kern J.-L. Huel C. Momenteau M. J. Org. Chem. 1993, 58: 2774

25c Fujimoto K. Miyata T. Aoyama Y. J. Am. Chem. Soc. 2000, 122: 3558

25d Chen X. Hui L. Foster D. Drain C. Biochemistry 2004, 43: 10918

25e Li G. Pandey S. Graham A. Dobhal M. Ricky M. Chen Y. Gryshuk A. Rittenhouse-Olson K. Oseroff A. Pandey R. J. Org. Chem. 2004, 69: 158

25f Chen X. Drain C. Drug Design Rev. - Online 2004, 1: 215 ; www.ingentaconnect.com/content/ben/ddro

26a Chandler J. Williams E. Slavin J. Best J. Rogers S. Cancer 2003, 97: 2035

26b Kumamoto K. Goto Y. Sekikawa K. Takenoshita S. Ishida N. Kawakita M. Kannagi R. Cancer Res. 2001, 61: 4620

27 Wöhrle D. Schnurpfeil G. Knothe G. Dyes Pigments 1992, 18: 91

28 Zemplén G. Ber. Dtsch. Chem. Ges. 1927, 60: 1555

29 Sommerauer M. Rager C. Hanack M. J. Am. Chem. Soc. 1996, 118: 10085

30a Wolfrom ML. Thompson A. Methods in Carbohydrate Chemistry Vol. 2: Whistler RL. Wolfrom ML. Academic Press; New York: 1963. p.211

30b Mikamo M. Carbohydr. Res. 1989, 191: 150

31a Scheurer PG. Smith F. J. Am. Chem. Soc. 1954, 76: 3224

31b Matta KL. Girotra RN. Barlow J. J. Carbohydr. Res. 1975, 43: 101

32 Sorg BL. Hull WI. Kleim HC. Mier W. Wiessler M. Carbohydr. Res. 2005, 340: 181

33 Petrig J. Schibli R. Dumas C. Alberto R. Schubiger PA. Chem. Eur. J. 2001, 7: 1868