Recent Advances in Nucleosides: Chemistry and Chemotherapy

545 Pages·2002·23.69 MB·English

by  C.K. Chu

RECENT ADVANCES IN NUCLEOSIDES"
CHEMISTRY AND CHEMOTHERAPY
This Page Intentionally Left Blank
RECENT ADVANCES IN NUCLEOSIDES:
CHEMISTRY AND CHEMOTHERAPY
Edited by
C.K. CHU
2002
ELSEVIER
Amsterdam - Boston - London - New York -Oxford - Paris
San Diego- San Francisco- Singapore- Sydney- Tokyo
ELSEVIER SCIENCE B.V.
Sara Burgerhartstraat 25
P.O. Box 211, 1000 AE Amsterdam, The Netherlands
(cid:14)9 2002 Elsevier Science B.V. All rights reserved.
This work is protected under copyright by Elsevier Science, and the following terms and conditions apply to
its use:
Photocopying
Single photocopies of single chapters may be made for personal use as allowed by national copyright laws.
Permission of the Publisher and payment of a fee is required for all other photocopying, including multiple or
systematic copying, copying for advertising or promotional purposes, resale, and all forms of document
delivery. Special rates are available for educational institutions that wish to make photocopies for non-profit
educational classroom use.
Permissions may be sought directly from Elsevier Science via their homepage (http://www.elsevier.com) by
selecting 'Customer support' and then 'Permissions'. Alternatively you can send an e-mail to:
[email protected], or fax to: ([phone].
In the USA, users may clear permissions and make payments through the Copyright Clearance Center, Inc.,
222 Rosewood Drive, Danvers, MA 01923, USA; phone: (+1) (978) 7508400, fax: (+1) (978) 7504744, and in
the UK through the Copyright Licensing Agency Rapid Clearance Service (CLARCS), 90 Tottenham Court
Road, London WlP 0LP, UK; phone: [phone]; fax: [phone]. Other countries may
have a local reprographic rights agency for payments.
Derivative Works
Tables of contents may be reproduced for internal circulation, but permission of Elsevier Science is required
for external resale or distribution of such material.
Permission of the Publisher is required for all other derivative works, including compilations and translations.
Electronic Storage or Usage
Permission of the Publisher is required to store or use electronically any material contained in this work,
including any chapter or part of a chapter.
Except as outlined above, no part of this work may be reproduced, stored in a retrieval system or transmitted
in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without prior
written permission of the Publisher.
Address permissions requests to: Elsevier Science Global Rights Department, at the fax and e-mail addresses
noted above.
Notice
No responsibility is assumed by the Publisher for any injury and/or damage to persons or property as a matter
of products liability, negligence or otherwise, or from any use or operation of any methods, products,
instructions or ideas contained in the material herein. Because of rapid advances in the medical sciences, in
particular, independent verification of diagnoses and drug dosages should be made.
First edition 2002
Library of Congress Cataloging in Publication Data
A catalog record from the Library of Congress has been applied for.
British Library Cataloguing in Publication Data
A catalogue record from the British Library has been applied for.
ISBN: 0-444-50951-8
The paper used in this publication meets the requirements of ANSI/NISO Z39.48-1992 (Permanence of
Paper).
Printed in The Netherlands.
CONTENTS
Preface ix
DAVID CHU
College of Pharmacy, The University of Georgia, Athens, GA, USA
1. Mission oriented research: An experience in Dr. Jack J. FOX'Sla boratory 1
KYOICHI A. WATANABE
Pharmasset, Atlanta, GA, USA
2. Development of new radical reactions with a vinylsilyl group and
their application to the synthesis of branched-chain sugar nucleosides 21
SATOSHI SHUTO, MAKIKO KANAZAKI, ISAMU SUGIMOTO,
SATOSHI ICHIKAWA, YUKI NAGASAWA, YOSHIHITO UENO,
HIROSHI ABE, NORIAKI MINAKAWA, MAKOTO SUKEDA,
TETSUYA KODAMA, MAKOTO NOMURA and AKIRA MATSUDA
Hokkaido University, Sapporo, JAPAN
3. Synthesis of purine acyclonucleosides via ribofuranose-ring cleavage
of purine nucleosides by diisobutylaluminum hydride 57
KOSAKU HIROTA, YASUNARI MONGUCHI and HIRONAO SAJIKI
Gifu Pharmaceutical University, Gifu, JAPAN
4. The chemistry of nucleoside and dinucleotide inhibitors of
nosine monophosphate dehydrogenase (IMPDH) 71
KRZYSZTOF PANKIEWICZ and BARRY M GOLDSTEIN
Pharmasset, Atlanta, GA, USA
5. Nucleoside and nucleotide prodrugs 91
JOHN S. COOPERWOOD, GIUSEPPE GUMINA,
F. DOUGLAS BOUDINOT, and CHUNG K. CHU
The University of Georgia, Athens, GA, USA
6. Antiviral Isonucleosides: discovery, chemisry and chemical biology 149
VASU NAIR
University of Iowa, Iowa City, IA, USA
V
7. Synthesis and biological activity of isopolar acyclic nucleotide analogs 167
ANTON~NH OLY
Academy of Sciences of the Czech Republic, Prague, CZECH REPUBLIC
8. Synthesis of pyranose nucleosides and related nucleosides with
a six-membered carbohydrate mimic 239
PIET HERDEWIJN
Rega Institute for Medical Research, Leuven, BELGIUM
9. 5'-Norcarbanucleosides in L-like configurations 29 1
STEWART W. SCHNELLER, KATHERINE L. SELEY,
VISHNUMURTHY R. HEGDE and VASANTHAKUMAR P. RAJAPPAN
Auburn University, Auburn, AL, USA
10. Tricyclic nucleosides revisited 299
KATHERINE L. SELEY
Georgia Institute of Technology, Atlanta, GA, USA
11. Unusual analogues of nucleosides: chemistry and biological activity 327
JIRI ZEMLICKA
Wayne State University School of Medicine, Detroit, MI, USA
12. Lithiation-based silylation and stannylation for nucleoside synthesis 359
HIROKI KUMAMOTO', KEISUKE KATO' and HIROMICHI TANAKA'
1 Showa University, Tokyo, JAPAN
2T oho University, Chiba, JAPAN
13. Purine metabolism in parasites: potential targets for chemotherapy 377
MAHMOUD H. EL KOUNI
University of Alabama at Birmingham, Birmingham, AL, USA
14. Antiviral P-L-nucleosides specific for hepatits B virus infection 417
JEAN-PIERRE SOMMADOSSI
Novirio Pharmaceuticals, Inc., Cambridge, MA, USA
vi
15. Antiviral activity of nucleoside analogues: the BVDU connection 433
ERIK DE CLERCQ
Rega Institute for Medical Research, Leuven, BELGIUM
16. The role of the cellular deoxynucleoside kinases in activation 455
of nucleoside analogs used in chemotherapy
STAFFAN ERIKSSON and LIYA WANG
Swedish University of Agricultural Sciences, Uppsala, SWEDEN
17. Cellular transport of nucleotide analogs 477
TOMAS CIHLAR, DAMIAN MCCOLL and NORBERT BISCHOFBERGER
Gilead Sciences, Foster City, CA, USA
18. 5-Aza-7-deazapurines: synthesis and properties 505
of nucleosides and oligonucleotides
FRANK SEELA and HELMUT ROSEMEYER
Universit~it Osnab~ck, Osnabrtick, GERMANY
vii
This Page Intentionally Left Blank
PREFACE
The chemistry and biology of nucleosides and nucleotides has undoubtedly been a very
exciting field for the past fifty years, particularly to those investigators who have been
closely involved in the area. If we compare the field of nucleosides and nucleotides
to an apple tree, the early fifties and mid-sixties were the main root-, trunk-, and
branch-growing periods, and the next thirty years from the middle sixties to mid-nineties
have been the fruit harvesting period. As we all know from our experience, without
strong roots, a sturdy trunk and copious branches, we would not expect to harvest
abundant and delicious fruits in the fall. Fortunately, we have been harvesting abundant
and delicious fruits of nucleosides for the past thirty years. Particularly, during the
last twenty years, we have witnessed a number of clinically useful nucleosides being
developed as antiviral and anticancer agents. Furthermore, it doesn't appear likely that
this rate of development of nucleosides as chemotherapeutic agents will be slowing
down for the foreseeable future. However, those of us who are still in the field and enjoy
the dividend of the fruit tree planted a half century ago should not forget those who
nurtured the nucleoside tree at the early stage of the field. Thus, this book is dedicated
to Dr. Jack Fox, who is one of the pioneers in nucleoside chemistry. He dedicated his
entire half-century career to the chemistry of nucleosides at Memorial Sloan-Kettering
Institute Cancer Center, New York, until his retirement in 1987. We, the contemporary
nucleoside chemists and biochemists, are greatly indebted to his contribution in the
chemistry and biology of nucleosides and nucleotides.
The chapters in this book are mainly based on the symposium honoring Dr. Fox,
which was held as a satellite symposium of the Round Table in September of 2000.
I would like to express my sincere appreciation to contributing authors for this
book, and I would also like to thank those who helped the symposium as chairs
(Drs. Bergstrom, Meyer, Lopez, Secrist, Bischofberger, Kalman, Herdewijn, Colacino,
Eriksson, Broom, Rabi, Cook, Seela, Tanaka, and L. Townsend). I would like to
recognize those pharmaceutical firms (Lilly Research Laboratories, Microbiologica,
Bukwang Pharmaceuticals, Noviro, Pharmasset, Yamasa, Tiho Pharmaceuticals, and
Gilead Sciences) who contributed their financial assistance for the symposium.
My special thanks goes to Drs. Carlos Lopez and Joseph Colacino of Lilly Research
Laboratories, and Dr. Jaime Rabi of Microbiologica, who arranged significant financial
contributions for the symposium. Without their help, we would not have had such a high
quality symposium that was enjoyed by all who attended. Finally, my special thanks
goes to my assistant, Ms. Wendy Nix, for her dedication and hard work to complete the
difficult task, from beginning to end, of the symposium as well as this book.
David Chu
College of Pharmacy
The University of Georgia
Athens, Georgia
June, 2001
ix