Search
This Journal
This Journal
Anywhere
Quick Search in Journals
Enter words / phrases / DOI / ISBN / keywords / authors / etc
Access type:Only show content I have full access toOnly show Open Access
Advanced Search
0 My Cart
Sign in
Institutional Access

System Upgrade on Tue, May 28th, 2024 at 2am (EDT)

Existing users will be able to log into the site and access content. However, E-commerce and registration of new users may not be available for up to 12 hours.
For online purchase, please visit us again. Contact us at customercare@wspc.com for any enquiries.

ArticlesNo Access

Synthesis and characterization of 1,8(11),15(18),22(25)-tetraglycosylated zinc(II) phthalocyanines

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Search for more papers by this author

,

Alexey Lyubimtsev

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Ivanovo State University of Chemistry and Technology, F. Engels str. 7, 15300 Ivanovo, Russia

Search for more papers by this author

,

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Corresponding author, tel: +49 7071-29-72432, fax: +49 7071-29-5268.

SPP full member in good standing.

Search for more papers by this author

, and

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Corresponding author.

Search for more papers by this author

https://doi.org/10.1142/S1088424610002343Cited by:19 (Source: Crossref)

Abstract

In continuation of our work on glycosylated phthalocyanines, a new series of 1,8(11),15(18),22(25)-tetraglycosylated zinc(II) phthalocyanines (PcZns) have been synthesized and characterized. 3-glycosylated phthalonitriles were synthesized through nitrite displacement in 3-nitrophthalonitrile with anomerically deprotected glycoses. The anomerically glycosylated phthalonitriles were then treated with hexamethyldisilazane (HMDS), trimethylsilyltriflate (TMSOTf) and zinc salt in DMF to form the corresponding acetyl-protected PcZns, followed by deprotection of acetyl groups by NaOMe in methanol/DMSO mixture. The formed unprotected tetraglycosylated PcZns are highly soluble in water, which is a necessary condition for potential biological applications.

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

X. Alvarez-Micoet al., Tetrahedron Lett. 47, 3283 (2006), DOI: 10.1016/j.tetlet.2006.03.029. Crossref, Web of Science, Google Scholar
X. Alvarez-Micoet al., Synthesis 2186 (2007). Google Scholar
Z. Iqbal, M. Hanack and T. Ziegler, Tetrahedron Lett. 50, 873 (2009), DOI: 10.1016/j.tetlet.2008.12.015. Crossref, Web of Science, Google Scholar
Z. Iqbal, M. Hanack and T. Ziegler, Tetrahedron Lett. 50, 5681 (2009), DOI: 10.1016/j.tetlet.2009.07.127. Crossref, Web of Science, Google Scholar
A. R. M. Soareset al., Carbohydr. Res. 344, 507 (2009), DOI: 10.1016/j.carres.2008.12.009. Crossref, Web of Science, Google Scholar
J.-Y. Liuet al., Org. Biomol. Chem. 7, 1583 (2009), DOI: 10.1039/b822128f. Crossref, Web of Science, Google Scholar
U. Kumruet al., J. Porphyrins Phthalocyanines 12, 1090 (2008), DOI: 10.1142/S1088424608000443. Link, Web of Science, Google Scholar
A. O. Ribeiroet al., Tetrahedron Lett. 47, 9177 (2006), DOI: 10.1016/j.tetlet.2006.10.155. Crossref, Web of Science, Google Scholar
C.-F. Choiet al., Org. Biomol. Chem. 6, 2173 (2008), DOI: 10.1039/b802212g. Crossref, Web of Science, Google Scholar
P.-C. Loet al., J. Med. Chem. 50, 2100 (2007), DOI: 10.1021/jm061415j. Crossref, Web of Science, Google Scholar
M. R. Reddyet al., Synlett 628 (2007). Google Scholar
P. Leeet al., Tetrahedron Lett. 46, 1551 (2005), DOI: 10.1016/j.tetlet.2004.12.137. Crossref, Web of Science, Google Scholar
Y. Zorluet al., Photochem. Photobiol. Sci. 8, 312 (2009), DOI: 10.1039/b817348f. Crossref, Web of Science, Google Scholar
N. C. Yates, J. Moan and A. Western, J. Photochem. Photobiol. B 4, 379 (1990), DOI: 10.1016/1011-1344(90)85017-Q. Crossref, Web of Science, Google Scholar
D. Woehrleet al., J. Photochem. Photobiol. B 21, 155 (1993). Crossref, Web of Science, Google Scholar
M. Shopovaet al., J. Photochem. Photobiol. B 23, 35 (1994), DOI: 10.1016/1011-1344(93)06983-A. Crossref, Web of Science, Google Scholar
M. Camerinet al., Eur. J. Cancer 41, 1203 (2005), DOI: 10.1016/j.ejca.2005.02.021. Crossref, Web of Science, Google Scholar
N. Brasseuret al., J. Med. Chem. 37, 415 (1994), DOI: 10.1021/jm00029a014. Crossref, Web of Science, Google Scholar
G. Liet al., J. Org. Chem. 69, 158 (2004), DOI: 10.1021/jo030280b. Crossref, Web of Science, Google Scholar
X. Chenet al., Biochemistry 43, 10918 (2004), DOI: 10.1021/bi049272v. Crossref, Web of Science, Google Scholar
Z. Iqbalet al., Synthesis (2010). Google Scholar
B. C. Wilson and W. P. Jeeves, Photodynamic Therapy of Cancer. Photomedicine 2, eds. E. Ben-Hur and I. Rosenthal (CRC Press, Boca Raton, FL, 1987) pp. 127–177. Google Scholar
X. Alvarez-Micoet al., Carbohydr. Res. 342, 440 (2007), DOI: 10.1016/j.carres.2006.11.017. Crossref, Web of Science, Google Scholar
M. C. T. Hartman and J. K. Coward, J. Am. Chem. Soc. 124, 10036 (2002), DOI: 10.1021/ja0127234. Crossref, Web of Science, Google Scholar
Z. Viragiet al., Carbohydr. Res. 62, 105 (1978). Web of Science, Google Scholar

Journal cover image

Vol. 14, No. 06

Metrics

Downloaded 83 times

History

Received 9 November 2009

Accepted 28 January 2010

Keywords