Chemistry of Nucleosides and Nucleotides: Volume 3

560 Pages·1994·10.39 MB·English

by  Maria N. Preobrazhenskaya

Chemistry of
Nucleosides
and Nucleotides
Volume 3
Chemistry of
Nucleosides
and Nucleotides
Volume 3
Edited by
Leroy B. Townsend
University ofM ichigan
Ann Arbor, Michigan
Springer Science+ Business Media, LLC
Library of Congress Cataloging in Publication Data
(Revised for voi. 3)
Chemistry of nucleosides and nucleotides.
Includes bibliographical references and indexes.
1. Nucleotides. 2. Nucleosides. 1. Townsend, Leroy B.
QD435.N85C47 1988 547.7'9 88-22359
ISBN 978-1-4757-9669-8 ISBN 978-1-4757-9667-4 (eBook)
DOI 10.1007/978-1-4757-9667-4
ISBN 978·1·4757·9669·8
© 1994 Springer Science+Business Media New York
Originally published by Plenum Press, New York in 1994
Softcover reprint of the hardcover 1st edition 1994
AII rights reserved
No part ofthis book may be reproduced, stored in a retrieval system, or transmitted
in any form or by any means, electronic, mechanical, photocopying, microfilming,
recording, or otherwise, without written permission from the Publisher
Contributors
Stanis'av Chladek, Michigan Cancer Foundation, Detroit, Michigan 48201
llya A. Korbukh, Russian Academy of Medical Sciences, Cancer Research Center,
Moscow 115478" Russia. Present address: Beckman Instruments, 2500 Harbor
Boulevard, Fullerton, California 92634
Wolfgang Pfleiderer, Faculty of Chemistry, University of Konstanz, D-7750
Konstanz, Germany
Maria N. Preobrazhenskaya, Russian Academy of Medical Sciences, Institute of
New Antibiotics, Moscow 119867, Russia
Gordon Shaw, Department of Chemistry and Chemical Technology, University of
Bradford, Bradford, West Yorkshire, BD7 lDP, England
Kyoichi A. Watanabe, Laboratory of Organic Chemistry, Sloan-Kettering
Institute for Cancer Research, Sloan-Kettering Division, Graduate School of
Medical Sciences, Cornell University, New York, New York lO021
v
Preface
The present volume is the third volume of a projected four-volume series. This
volume contains the following chapters: ."The Synthesis and Reactions of Pyrrole,
Pyrazole, Triazole, Indole, Indazole, and Benzotriazole Nucleosides and
Nucleotides," "The Synthesis, Reactions, and Properties of the 2'(3')-O-Aminoacyl
and Peptidyl Nucleosides and Nucleotides," "Syntheses and Reactions of Bicyclic
Heterocyclic Nucleosides and Nucleotides," "The Synthesis and Chemistry of
Imidazole and Benzimidazole Nucleosides and Nucleotides," and "The Chemistry of
C-Nucleosides."
Each chapter is comprehensive in nature and should provide a ready reference
source for not only the novice but also the experienced investiga tor or researcher.
The chapters have been prepared by authors with considerable experience in each
particular area of research, and this has resulted in a lucid presentation of each
well-defined area.
These volumes (1-3) were designed with medicinal chemists, medicinal organic
chemists, organic chemists, carbohydrate chemists, physical chemists, and biological
chemists in mind. However, because of the tremendous recent interest in this
research area owing to the biological and chemotherapeutic evaluation ofnucleosides
and nucleotides as anticancer, antiviral, and antiparasitic agents, these volumes
should also be valuable additions to the libraries of virologists, biochemical phar
macologists, oncologists, and pharmacologists.
We would like to thank the authors for their enthusiasm and help in making
these volumes available to the scientific community.
Leroy B. Townsend
Ann Arbor, Michigan
vii
Contents
Chapter 1
The Synthesis and ReactioDs of Pyrrole, Pyrazole, Triazole, Iadole,
Iadazole, and Beazotriazole Nucleosides and Nucleotides
Maria N. Preobrazhenskaya and Ilya A. Korbukh
1. Introduction .................................................... 1
2. Pyrrole and Indole Nucleosides and Nucleotides ...................... 2
2.1. Glycosylation of Pyrroles, Indoles, and Related Compounds ....... 2
2.2. Synthesis of Indole and Pyrrole Nucleosides by the "Indoline-
Indole" Method ............................................ 12
2.3. Physicochemical Properties of Indole and Pyrrole Nucleosides:
Configurational and Conformational Studies .................... 24
2.4. Chemical Properties of Indole Nucleosides ...................... 28
2.5. l-Glycosyltryptamines, trans-p-( l-Glycosyl-indol-3-yl)acrylic Acids,
and l-Glycosylharmanes ..................................... 31
2.6. Indole Nucleotides .......................................... 33
2.7. "Double-Headed" Nucleosides Containing the Indole Nucleus ..... 34
2.8. Isatin Nucleosides . . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . 35
2.9. Maleimide, Succinimide, and Phthalimide Nucleosides . . . . . . . . . . . . 37
2.10. Derivatives Related to C-Glycosylindoles and C-Glycosylpyrroles ... 42
3. Pyrazole, Triazole, Indazole, and Benzotriazole Nucleosides and
Nucleotides ..................................................... 47
3.1. Synthesis ofPyrazole and Triazole Nucleosides .................. 47
3.2. Chemi cal Properties of Pyrazole and Triazole Nucleosides ......... 66
3.3. Synthesis ofIndazole and Benzotriazole Nucleosides .............. 80
3.4. Chemical Properties ofIndazole and Benzotriazole Nucleosides . . . . . 86
3.5. "Double-Headed" Nucleosides Containing Benzotriazole Nucleus . . . 89
3.6. Investigation of the Structure of Pyrazole, Triazole, Indazole, and
Benzotriazole N ucleosides .................................... 90
3.7. Pyrazole, Triazole, Indazole, and Benzotriazole Nucleotides ....... 94
4. References ...................................................... 97
Contents
Chapter 2
The Synthesis, Reactions, and Properties of the 2'(3')-O-Aminoacyl and
Peptidyl Nucleosides and Nucleotides
Stanislav Chladek
1. 2'(3')-0-Aminoacylnucleosides and Nucleotides Derived from the
3'-Terminus ofaa-tRNA .......................................... 107
2. Properties of the Aminoacyl Bond, Hydrolysis, and Isomerization ........ 108
3. Synthesis and Reactions of2'(3')-0-Aminoacylnucleosides .............. 110
4. Synthesis and Reactions of2'(3')-O-Aminoacylnucleotides .............. 117
5. Synthesis and Reactions of 2' (3')-O-Aminoacyloligonucleotides .......... 119
6. Syntheses of 2'(3')-0-Peptidyl (N-Acylaminoacyl) Nucleosides and
Nucleotides ..................................................... 132
7. Synthesis and Reactions of Puromycin Analogues of 2'(3')-0-
Aminoacylnucleosides and Nucleotides .............................. 134
8. Nucleoside Antibiotics Related to Aminoacylnucleosides . . . . . . . . . . . . . . .. 137
9. Preparation of 2'(3')-O-Aminoacylnucleosides and Nucleotides via
Degradation of Charged tRNAs .................................... 139
10. Biological Activity of 2'(3')-0-Aminoacyl, 2'(3')-0-Peptidyl Nucleosides
and Nucleotides ................................................. 139
II. Abbreviations ................................................... 140
12. References ...................................................... 140
Chapter 3
Syntheses and Reactions of Bicyclic Heterocyclic Nucleosides
and Nucleotides
Wolfgang Pfieiderer
1. Bicyclic Benzo-Fused 6-Membered Ring Nitrogen Heterocyclic
Nucleosides and Nucleotides ....................................... 145
1.1. Quinoline Glycosides ........................................ 145
1.2. Isoquinoline Glycosides ...................................... 149
1.3. Cinnoline Glycosides ........................................ 150
1.4. Phthalazine Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 152
1.5. Quinazoline Glycosides ...................................... 154
1.6. Quinoxaline Glycosides ...................................... 162
1.7. 1,3-Benzoxazine Glycosides ...... . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 165
1.8. 1,2,3-Benzotriazine Glycosides ................................ 166
2. Bicyclic Pyrido-Fused 5- and 6-Membered Ring Nitrogen Heterocyclic
Nucleosides (Sugar Attachment at the Pyridine Moiety) .. . . . . . . . . . . . . .. 167
2.1. Pyrrolo[3,2-cJpyridine Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 168
2.2. Imidazo[4,5-bJpyridine Nucleosides .. . . . . . . . . . . . . . . . . . . . . . . . . .. 168
2.3. v-Triazolo[4 ,5-b Jpyridine Glycosides ........................... 170
2.4. 1,8-Naphthyridine Glycosides ..... . . . . . . . . . . . . . . . . . . . . . . . . . . .. 170
2.5. 2,7-Naphthyridine Nucleotides .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 172
Cont_t.
2.6. Pyrido[2,3-d]pyrimidine Glycosides ............................ 172
2.7. Pyrido[2,3-e]-1,2,4-triazine Glycosides . . . . . . . . . . . . . . . . . . . . . . . . .. 176
3. Bicyclic Pyrimido-Fused 5- and 6-Membered Ring Heterocyclic
Nucleosides (Sugar Attachment at the Pyrimidine Moiety) ............. 176
3.1. Pyrrolo[2,3-d]pyrimidine Glycosides ........................... 176
3.2. Furo- and Pyranopyrimidine Glycosides ........................ 179
3.3. Thieno[2,3-d]pyrimidine Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . .. 180
3.4. Oxazolo-pyrimidine Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 183
3.5. Thiazolo-pyrimidine Glycosides ............................... 184
3.6. Pyrazolo[3,4-d]pyrimidine Glycosides .......................... 189
3.7. v-Triazolo[4 ,5-d]pyrimidine Glycosides ......................... 192
3.8. Pyrido[2,3-d]pyrimidine Glycosides ............................ 193
3.9. 1,4-0xathiino[2,3-d]pyrimidine Glycosides . . . . . . . . . . . . . . . . . . . . .. 195
3.10. Pyrimido[4,5-b]-1,4-oxazine Glycosides . ....... .. .. ... ...... .... 195
3.11. Pyrimido[5,4-e]-1,2,4-triazine Glycosides . . . . . . . . . . . . . . . . . . . . . . .. 196
3.12. Imidazo[4,5-d]pyridazine Glycosides ... ....... .. ..... ... ....... 197
4. Bicyclic S-Containing Nitrogen Heterocyclic Nucleosides ............... 198
4.1. 1, 2,5-0xadiazolo[4 ,5-d]-1 ,2,6-thiadiazine Glycosides . . . . . . . . . . . . .. 198
4.2. 1,2,5-Thiadiazolo[4,5-d]-1,2,6-thiadiazine Glycosides ............. 199
4.3. Imidazo[4,5-d]-1,2,6-thiadiazine Glycosides ..................... 199
4.4. 1,2,3-Triazolo[4,5-d]-1,2,6-thiadiazine Glycosides ................ 201
5. Heterocyclic Nucleosides of Nitrogen Bridgehead Bicyclic Systems (Sugar
Attachment at the 6-Membered Heteroring) ......................... 201
5.1. Imidazo[I,2-c]pyrimidine Glycosides . .. . .... .. ........ ... . .. ... 201
5.2. Pyrazolo[I,5-a]pyrimidine Glycosides .......................... 205
5.3. Triazolo-pyrimidine Glycosides ............................... 206
5.4. Tetrazolo[l,5-c]pyrimidine Glycosides . . . . . . . . . . . . . . . . . . . . . . . . .. 210
5.5. Imidazo[l ,2-a ]-1 ,3,5-triazine Glycosides ........................ 210
5.6. Pyrazolo[I,5-a]-s-triazine Glycosides ........................... 211
5.7. Pyrimido[I,6-a]pyrimidine Glycosides ......... ........ ...... ... 212
5.8. Pyrimido[I,6-a]-1,3,5-triazine Glycosides ....................... 213
6. Pteridine Nucleosides and Nucleotides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 214
6.1. Pteridine N ucleosides ........................................ 214
6.2. Pteridine Nucleotides ........................................ 252
7. References ...................................................... 256
Chapter 4
The Synthesis and CheJllistry of Imidazole and Benzim.idazole Nucleosides
and Nucleotides
Gordon Shaw
1. Introduction .................................................... 263
1.1. Abbreviations.............................................. 264
1.2. Functions of Imidazole Nucleosides and Nucleotides in Living
Systems ................................................... 265
1&Îi Cord_ta
1.3. Aminoimidazole Nucleotides in the de Novo Biosynthesis of Purine
Nucleotides ................................................ 266
1.4. Enzymes of de Novo Purine Nucleotide Biosynthesis ............... 269
1.5. Imidazole Nucleosides and Nucleotides in Histidine Biosynthesis . . .. 271
1.6. Histamine Metabolism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 271
2. Synthesis ofImidazo1e Nucleosides and Nucleotides . . . . . . . . . . . . . . . . . . .. 272
2.1. Introduction............................................... 272
2.2. Heavy Metal Method ....................................... 273
2.3. Fusion Methods ............................................ 283
2.4. Synthesis from Purine Nucleosides and Nucleotides ............... 289
2.5. Synthesis from Glycosylamines ................................ 300
2.6. Synthesis from Pyrimidine Nucleosides ......................... 315
2.7. C-Nucleosides.............................................. 316
3. Reactions ofImidazole Nucleosides and Nucleotides ................... 318
3.1. Introduction............................................... 318
3.2. Conversion to Purine Nucleosides and Nucleotides ............... 318
3.3. Reactions of the Amino Group in 5(4)-Aminoimidazole
Nucleosides and Nucleotides .................................. 330
3.4. Reactions of the Carboxyl Group in Imidazo1e-4(5)-carboxylic
Acid Nucleosides and Nucleotides ............................. 335
3.5. Miscellaneous Reactions ..................................... 348
4. Miscellaneous Imidazole Nucleosides and Nucleotides . . . . . . . . . . . . . . . . .. 359
4.1. Coenzyme Analogues .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 359
4.2. 5-Amino-l-(5-deoxy-5-S-homocysteinyl-p-n-ribofuranosyl) imidazole-
4-carboxamide ............................................. 360
4.3. Bredinin................................................... 361
4.4. Casimiroedine.............................................. 362
4.5. Azomycin Ribofuranoside .................................... 363
4.6. Nikkomycins, Polyoxin N, and Neopolyoxins .................... 364
4.7. 4-p-n-Erythro-furanosylimidazole............................... 365
5. Biological Activity of Some Imidazole Nucleosides and Nucleotides . . . . . .. 366
5.1. Introduction............................................... 366
5.2. Enzyme Inhibition by Imidazole Nucleosides and Nucleotides . . . . .. 368
6. Benzimidazole and Related N ucleosides ............................. 369
6.1. Introduction............................................... 369
6.2. Synthesis ofBenzimidazole Nucleosides ......................... 369
6.3. Synthesis of Benzotriazole and Related Nucleosides .. . . . . . . . . . . . .. 373
7. Physical Properties of Imidazole and Benzimidazole Nucleosides and
Nucleotides ..................................................... 377
7.1. lonization Constants ........................................ 377
7.2. UV Absorption Spectra . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 377
7.3. lH NMR Spectra ................................... , .. .. . .. 395
7.4. Circular Dichroism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 411
8. References ...................................................... 412