Abstract
Hyaluronidase is one of the most important enzymes in the development of many diseases. In this study, a series of xyloside analogues bearing a triazole and tetrazole at the anomeric position were prepared from xylosylthioureas and evaluated their inhibitory effects on the hyaluronidase. Triazole and tetrazole skeletons were formed via the Hg(OAc)2-mediated desulfurizative cyclization through carbodiimide intermediates. According to in vitro anti-hyaluronidase assay, tetrazole-xylosides having p-chloro- or p-nitro-substitution exhibited the high inhibition rates, whereas the compound having p-trifluoromethyl group on the structure did not show the potency. Our results demonstrated the importance of tetrazole-xylosides as hyaluronidase inhibitors.
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Acknowledgments
The authors gratefully thank Prof. Masahiro Ebihara for X-ray analysis. Our thanks are due to Mr. Shota Fukuno for his technical support.
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Kato, Y., Ninomiya, M., Yamaguchi, Y. et al. Synthesis of triazole- and tetrazole-xyloside analogues as potent hyaluronidase inhibitors. Med Chem Res 24, 1180–1188 (2015). https://doi.org/10.1007/s00044-014-1203-x
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DOI: https://doi.org/10.1007/s00044-014-1203-x