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Synthesis of per-sulfated flavonoids using 2,2,2-trichloro ethyl protecting group and their factor Xa inhibition potential
[Display omitted] The synthesis of per-sulfated flavonoids, organic compounds with multiple sulfate groups, is challenging. We present here a two-step synthesis of fully sulfated flavonoids in high overall yields using the 2,2,2-trichloroethyl moiety as a protecting group. The two-step synthesis res...
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Published in: | Bioorganic & medicinal chemistry 2005-03, Vol.13 (5), p.1783-1789 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that cite this one |
Online Access: | Get full text |
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Summary: | [Display omitted]
The synthesis of per-sulfated flavonoids, organic compounds with multiple sulfate groups, is challenging. We present here a two-step synthesis of fully sulfated flavonoids in high overall yields using the 2,2,2-trichloroethyl moiety as a protecting group. The two-step synthesis results in exclusive formation of the per-sulfated product in contrast to common sulfating agents that yield differentially sulfated mixture of compounds. Most per-sulfated flavonoids studied are activators of antithrombin for accelerated inhibition of factor Xa, a key enzyme of the blood coagulation cascade. As a group the per-sulfated flavonoids possess a range of factor Xa inhibition potential. |
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ISSN: | 0968-0896 1464-3391 |
DOI: | 10.1016/j.bmc.2004.11.060 |