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Glycosidation, 15. — Anticancer agents, 11. Development of selective anticancer agents synthesis of acetal-β-glucosides from cytotoxic alcohols

✍ Scribed by Tietze, Lutz F. ;Beller, Matthias

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
504 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The reaction of trimethylsilyl 2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranoside 7 with hexanal and the trimethylsilyl ethers 9a–c of cytotoxic alcohols 4a–c in the presence of catalytic amounts of TMS triflate yields the acetal‐β‐glucosides 10a–c. In a similar way, the acetal‐α‐glucosides 12a, b are obtained from 8, hexanal, and 9a, b. In addition, the highly acid‐sensitive acetal‐β‐glucoside 13 is synthesized from 7, acetone, and 9a. Deacetylation of 10a, 10b, and 13 by solvolysis affords the deprotected acetal‐β‐glucosides 11a, 11b, and 14, respectively, which will be tested as selective anticancer agents.

📜 SIMILAR VOLUMES

Glycosidation, 13; anticancer agents, 10
Glycosidation, 13; anticancer agents, 10. Novel stable bioactivated cyclophosphamide derivatives for selective cancer chemotherapy, synthesis of aldophosphamide acetal-glycosides and their glycoconjugates
✍ Tietze, Lutz F. ;Fischer, Roland ;Beller, Matthias ;Seele, Rainer 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 English ⚖ 826 KB

## Abstract Stimulation of tumor cell glycolysis in vivo leads to an increase of lactic acid formation and thus a decrease of pH in malignant tissue compared with a normal cell population. The difference in pH may be used to cleave a nontoxic prodrug selectively in a tumor to give a highly cytotoxi