Synthesis and in Vitro Antiviral Activities of [(Dihydrofuran-2-yl)oxy]methyl-phosphonate Nucleosides with 2-Substituted Adenine as Base
Fei Liu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorYingju Liu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorRui-Gang Xu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorGuifu Dai
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Life Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorLiu-Xi Zhao
Zhengzhou Trade and Industry School, 31 Middle Zhongyuan Road, Zhengzhou 450007, P. R. China
Search for more papers by this authorYafeng Wang
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorHong-Min Liu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorCorresponding Author
Feng-Wu Liu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Feng-Wu Liu, School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Piet Herdewijn, Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven
Search for more papers by this authorChristophe Pannecouque
Laboratory of Virology and Chemotherapy, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven
Search for more papers by this authorCorresponding Author
Piet Herdewijn
Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven
Feng-Wu Liu, School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Piet Herdewijn, Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven
Search for more papers by this authorFei Liu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorYingju Liu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorRui-Gang Xu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorGuifu Dai
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Life Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorLiu-Xi Zhao
Zhengzhou Trade and Industry School, 31 Middle Zhongyuan Road, Zhengzhou 450007, P. R. China
Search for more papers by this authorYafeng Wang
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorHong-Min Liu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Search for more papers by this authorCorresponding Author
Feng-Wu Liu
New Drug Research & Development Center, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Feng-Wu Liu, School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Piet Herdewijn, Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven
Search for more papers by this authorChristophe Pannecouque
Laboratory of Virology and Chemotherapy, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven
Search for more papers by this authorCorresponding Author
Piet Herdewijn
Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven
Feng-Wu Liu, School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, P. R. China
Piet Herdewijn, Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, BE-3000 Leuven
Search for more papers by this authorAbstract
The synthesis of [(2′,5′-dihydrofuran-2-yl)oxy]methyl-phosphonate nucleosides with a 2-substituted adenine base moiety starting from 2-deoxy-3,5-bis-O-(4-methylbenzoyl)-α-L-ribofuranosyl chloride and 2,6-dichloropurine is described. The key step is the regiospecific and stereoselective introduction of a phosphonate synthon at C(2) of the furan ring. None of the synthesized compounds showed significant in vitro activity against HIV, BVDV, and HBV.
Graphical Abstract
References
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