First example of an octa-glycoconjugated magnesium(II)porphyrazine. Issue 4 (27th January 2016)

• Record Type: Journal Article
• Authors: Klein, Thomas; Ziegler, Thomas
• Is Part Of: Tetrahedron letters. Volume 57:Issue 4(2016)
• Page Start: 495
• Page End: 497
• Publication Date: 2016-01-27
• Subjects: Glycoconjugate -- Porphyrazine -- Glycosidation -- Photosensitizer -- Photodynamic therapy; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.12.076
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: First synthesis of an octa-glycoconjugated magnesium(II)porphyrazine. Physical properties and characterization by spectroscopy and spectrometry. Possible application as photosensitizer in photodynamic therapy. Abstract: Treatment of disodium maleonitriledithiolate with 1, 2:3, 4-di- O -isopropylidene-6- O -trifluoromethanesulfonyl-α-d -galactopyranose gives 2, 3-bis(6-deoxy-1, 2:3, 4-di- O -isopropylidene-6-thio-α-d -galactopyranos-6-yl)maleonitrile in 87% yield. Heating of the latter with magnesium bis(butan-1-olate) in butan-1-ol affords [2, 3, 7, 8, 12, 13, 17, 18-octakis(6-deoxy-1, 2:3, 4-di- O -isopropylidene-6-thio-α-d -galactopyranos-6-yl)porphyrazinato]magnesium(II) in 53% yield. The glycoconjugated porphyrazine has an absorbance maximum at 673 nm and is a candidate as photosensitizer for photodynamic therapy.