A Convenient Synthesis and Biological Evaluation of Novel Pseudonucleosides Bearing a Thiazolidin‐4‐one Moiety by Tandem Staudinger/Aza‐Wittig/Cyclization | Zendy

Chen Hua | Zendy; Zhang Hongzhi | Zendy; Feng Junna | Zendy; Li Xiaoliu | Zendy; Jiao Lingling | Zendy; Qin Zhanbin | Zendy; Yin Qingmei | Zendy; Zhang Jinchao | Zendy

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A Convenient Synthesis and Biological Evaluation of Novel Pseudonucleosides Bearing a Thiazolidin‐4‐one Moiety by Tandem Staudinger/Aza‐Wittig/Cyclization

Author(s) -

Chen Hua,

Zhang Hongzhi,

Feng Junna,

Li Xiaoliu,

Jiao Lingling,

Qin Zhanbin,

Yin Qingmei,

Zhang Jinchao

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200900863

Subject(s) - chemistry , moiety , wittig reaction , intramolecular force , stereochemistry , tandem , combinatorial chemistry , composite material , materials science

Novel pseudonucleosides 3 and 4 bearing a thiazolidin‐4‐one moiety were firstly synthesized by a one‐pot, multicomponent, tandem Staudinger/aza‐Wittig/intermolecular nucleophilic addition/intramolecular cyclization process in good yields of 43.8–88.0 %. Deacetylation of 3 and 4 afforded compounds 5 and 6 , respectively. The structures of the new compounds were determined on the basis of the X‐ray crystal structures of 3b and 3e and by 1 H and 13 C NMR spectroscopy and high‐resolution mass spectrometry. The antitumor activity and the inhibitory activities against glycosidases and HIV reverse transcriptase of 5 and 6 were also evaluated.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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