Advanced generation of paeonol-phenylsufonyl derivatives as potential anti-HBV agents

Y. P. Huang; H. P. Shih; Y. C. Liang; H. H. Lin; M. C. Lin; C. W. Chen; T. J. Huang; Y. C. Kuo; C. C. Han; M. H. Hsu

doi:10.1039/C6RA06119B

Advanced generation of paeonol-phenylsufonyl derivatives as potential anti-HBV agents†

Y. P. Huang,^ai H. P. Shih,^a Y. C. Liang,^b H. H. Lin,^c M. C. Lin,^d C. W. Chen,^ef T. J. Huang,*^g Y. C. Kuo,*^h C. C. Han*^a and M. H. Hsu*^ij

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* Corresponding authors

^a Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan

^b Agricultural Biotechnology Research Center, Academia Sinica, Taipei 115, Taiwan

^c Division of Radiotherapy, Department of Oncology, Taipei Veterans General Hospital, Taipei 115, Taiwan

^d Biomedical Technology and Device Research Laboratories, Industrial Technology Research Institute, Hsinchu 30013, Taiwan

^e Department of Anesthesiology, China Medical University Hospital, Taichung 404, Taiwan

^f Department of Anesthesiology, School of Medicine, China Medical University, Taichung 404, Taiwan

^g School of Medicine, China Medical University, Taichung 404, Taiwan

^h Radiation Oncology, Show Chwan Memorial Hospital, Changhua City 50008, Taiwan

ⁱ Nuclear Science & Technology Department Center, National Tsing Hua University, Hsinchu 30013, Taiwan
E-mail: mhhsu@mx.nthu.edu.tw
Fax: +886-3-572-5974
Tel: +886-3-573-1180

^j Department of Chemistry, Tamkang University, New Taipei City 25137, Taiwan

Abstract

Hepatitis B virus (HBV) infection causes serious liver diseases, and the development of effective drugs for chronic hepatitis B treatment remains an important step towards the eradication of HBV worldwide. Recently, our group designed paeonol-phenylsulfonyl derivatives and found that the compound 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate (6f) had the most potent antiviral effect against HBV, with an IC₅₀ value of 0.36 μM and a high selectivity index (SI; TC₅₀/IC₅₀) of 47.75. In this research, we modified compound 6f with a 2-aminothiazole scaffold and generated 13 novel paeonol derivatives by utilizing various benzoyl and acyl chlorides. Among this new generation, compound 2-(2-benzamidothiazol-4-yl)-5-methoxyphenyl 4-methoxybenzenesulfonate (8a) showed the highest SI value of 59.14 which exceeds those of compound 6f and lamivudine (3TC), a commercially available antiviral drug. Hence, we believe that our studies may offer some useful information for the development of antiviral medicines.

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Advanced generation of paeonol-phenylsufonyl derivatives as potential anti-HBV agents†

Abstract

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Advanced generation of paeonol-phenylsufonyl derivatives as potential anti-HBV agents

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