SYNTHESIS OF THE POTENT INFLUENZA NEURAMINIDASE INHIBITOR 4-GUANIDINO NEU5AC2EN - X-RAY MOLECULAR-STRUCTURE OF 5-ACETAMIDO-4-AMINO-2,6-ANHYDRO-3,4,5-TRIDEOXY-D-ERYTHRO-L-GLUCO-NONONIC ACID

An efficient and high-yielding synthesis of 4-guanidino Neu5Ac2en, the potent anti-influenza A and B compound, is described. The route exploits a stereospecific introduction of the key nitrogen functionality at C-4 via an oxazoline intermediate. Three different methods for the final-step conversion...

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Published inJournal of the Chemical Society, Perkin Transactions 1 no. 9; pp. 1173 - 1180
Main Authors CHANDLER, M, BAMFORD, MJ, CONROY, R, LAMONT, B, PATEL, B, PATEL, VK, STEEPLES, IP, STORER, R, WEIR, NG, WRIGHT, M, WILLIAMSON, C
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1995
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2.2-A RESOLUTION
SIALIC-ACID
AMANTADINE
VIRUS
C-4
GLYCOPROTEIN
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Summary:An efficient and high-yielding synthesis of 4-guanidino Neu5Ac2en, the potent anti-influenza A and B compound, is described. The route exploits a stereospecific introduction of the key nitrogen functionality at C-4 via an oxazoline intermediate. Three different methods for the final-step conversion of the 4-amino into 4-guanidino derivatives are described. To explore the structure-activity relationship in this region of the molecule, a series of substituted guanidino derivatives were synthesized and their activity is described.
ISSN:0300-922X
1364-5463
DOI:10.1039/p19950001173