Synthesis and Biological Activities of Novel Guanidinoglucosides

Chem. J. Chinese Universities

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Synthesis and Biological Activities of Novel Guanidinoglucosides

LIAN Zhao-Bin¹, TIAN Xiao-Hong¹, CAO Ling-Hua^1,2*

1. College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China;
2. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China

Received:2006-07-31 Revised:1900-01-01 Online:2007-07-10 Published:2007-07-10
Contact: CAO Ling-Hua

Abstract

Abstract:

The reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 1 with 2-amino-4/6-substituted benzothiazoles 2a—2b gave glucosylthioureas(3a—3b), which then reacted with alkyl/aryl amine in the presence of HgCl₂ to afford a series of new poly-acetyl guanidinoglucosides(4a—4d, 5a—5d, 6a—6d and 7a—7d). Deacetylation of glycosyl was carried in the CH₃OH/CH₃ONa solution. The structures of the new compounds were established on the basis of elemental analyses, IR, ¹H NMR and mass spectral data and all compounds took β-configuration. The biological activities of these compounds have been evaluated. Compounds 4c, 6c, 8b and 8c showed anti-HIV-1 PR activity, compound 7c showed anti-influenza activity and compounds 5e, 7c and 7d showed inhibitory activity against angiotensin-converting enzyme(ACE) activity.

Key words: Glucopyranosyl isothiocyanate, Glucosylthiourea, Guanidinoglucoside, Biological activity

CLC Number:

O626.27

TrendMD:

LIAN Zhao-Bin¹, TIAN Xiao-Hong¹, CAO Ling-Hua^1,2*. Synthesis and Biological Activities of Novel Guanidinoglucosides[J]. Chem. J. Chinese Universities, doi: .

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Synthesis and Biological Activities of Novel Guanidinoglucosides

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