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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)