Synthesis of novel optically active cyclic phospholipid conjugates of Tegafur and uridine starting from L-serine

Article abstract of DOI:10.1080/10426500008043682

Starting from L-serine, cyclic thiophosphoramidate conjugates (2 and 3) of Tegatur and uridine were synthesized via a multiple-step procedure of esterification, cyclic phosphorylation, and sulfurization, etc. L-serinoate was N-alkylated, then cyclized with phosphorus oxychloride, and further reacted with N³-(2-hydroxyethyl) Tegafur to afford cyclic phospholipid conjugate 4. The resultants (2, 3, and 4) were successfully separated in the form of pure diastereomer by column chromatography on silica gel. Their configurations were discussed and assigned according to their NMR spectra. The asymmetric induction effects of the carbon-based chiral centre on the diastereomer preference were also observed in these two synthetic phosphorylation cyclizations. The bioassay on their antitumor activities is under investigation.

Full text of DOI:10.1080/10426500008043682

This article was downloaded by: [UOV University of Oviedo]
On: 24 October 2014, At: 02:28
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Phosphorus, Sulfur, and Silicon
and the Related Elements
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/gpss20
SYNTHESIS OF NOVEL
OPTICALLY ACTIVE CYCLIC
PHOSPHOLIPID CONJUGATES
OF TEGAFUR AND URIDINE
STARTING FROM L-SERINE
Zheng-Jie He a , Wen-Bin Chen a , Cheng-Xiang
Zhang a , Zheng-Hong Zhou And a & Chu-Chi Tang a
a The State Key Laboratory of Elemento-Organic
Chemistry , Institute of Elemento-Organic
Chemistry, Nankai University , Tianjin, 300071, P.R.
China
Published online: 04 Oct 2006.
To cite this article: Zheng-Jie He , Wen-Bin Chen , Cheng-Xiang Zhang , Zheng-Hong
Zhou And & Chu-Chi Tang (2000) SYNTHESIS OF NOVEL OPTICALLY ACTIVE CYCLIC
PHOSPHOLIPID CONJUGATES OF TEGAFUR AND URIDINE STARTING FROM L-SERINE,
Phosphorus, Sulfur, and Silicon and the Related Elements, 160:1, 223-232, DOI:
10.1080/10426500008043682
To link to this article: http://dx.doi.org/10.1080/10426500008043682
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and

are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions