The epothilones: an outstanding family of anti-tumor agents ; from soil to the clinic
Saved in:
| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Wien [u.a.]
Springer
2009
|
| Series: | Fortschritte der Chemie organischer Naturstoffe
90 |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Einzelaufnahme eines Zeitschr.-Bd. |
| Physical Description: | VIII, 260 S. Ill., graph. Darst. |
| ISBN: | 9783211782064 |
Staff View
MARC
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| 245 | 1 | 0 | |a The epothilones |b an outstanding family of anti-tumor agents ; from soil to the clinic |c authors: K.-H. Altmann ... |
| 264 | 1 | |a Wien [u.a.] |b Springer |c 2009 | |
| 300 | |a VIII, 260 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 0 | |a Fortschritte der Chemie organischer Naturstoffe |v 90 | |
| 500 | |a Einzelaufnahme eines Zeitschr.-Bd. | ||
| 650 | 4 | |a Antineoplastic agents | |
| 650 | 4 | |a Antineoplastic agents |x Effectiveness | |
| 650 | 0 | 7 | |a Epothilone |0 (DE-588)4505296-7 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Epothilone |0 (DE-588)4505296-7 |D s |
| 689 | 0 | |C b |5 DE-604 | |
| 700 | 1 | |a Altmann, Karl-Heinz |d 1957- |e Sonstige |0 (DE-588)137117639 |4 oth | |
| 856 | 4 | 2 | |m Digitalisierung UB Regensburg |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017051174&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-017051174 | ||
Record in the Search Index
| _version_ | 1804138524868345858 |
|---|---|
| adam_text | The Epothilones: An Outstanding
Family of Anti-Tumor Agents
From Soil to the Clinic
Contents
List of Contributors
...........................................
IX
1.
Preface
J. Mulzer
................................................ 1
2.
General Aspects
G. Höfle
................................................. 5
2.1.
History of Epothiione Discovery and Development
................. 5
2.1.1.
The Early Days
..................................... 5
2.1.2.
Industry Becomes Interested in Epothilones
-
and Loses
Interest Again
...................................... 7
2.1.3.
Re-Discovery of Epothiione in the Nineties
.................. 8
2.1.4.
Development of Epothilones as
Anticancer
Drugs
............. 10
2.1.5.
Epilogue
.......................................... 13
Acknowledgements
........................................... 13
References
................................................. 14
2.2.
Natural Epothilones
....................................... 16
2.2.1.
Isolation and Large Scale Production
...................... 16
2.2.2.
Structure of Epothilones and Related Compounds
.............. 20
2.2.3.
Physical and Chemical Properties
......................... 23
Acknowledgements
........................................... 27
References
................................................. 27
3.
Biosynthesis and Heterologous Production of Epothilones
R.
Müller................................................ 29
3.1.
Introduction
............................................. 29
3.2.
Feeding Studies and the Discovery of Natural Epothiione Variants
....... 32
VI
Contents
3.3.
Identification
of the Epothilone Biosynthesis Gene Cluster
............ 36
3.4.
Studies in vitro into the Biochemistry of Epothilone Assembly
......... 39
3.5.
Heterologous Expression and Genetic Engineering
of the Epothilone Biosynthesis Gene Cluster
...................... 43
3.6.
Nutrient Regulation in S. cellulosum and M. xanthus
................ 47
3.7.
Conclusions
............................................. 49
Acknowledgements
........................................... 50
References
................................................. 50
4.
Total Synthesis of Epothilones A-F
J. Mulzer, K. Prantz
........................................ 55
4.1.
Introduction
............................................. 56
4.2.
Synthesis Approaches to both the Epothilone A/C- and B/D-Series
...... 58
4.2.1.
Danishefsky Syntheses
................................. 58
4.2.2.
Nicolaou Syntheses
................................... 67
4.2.3.
Schinzer Synthesis
................................... 73
4.2.4.
Sinha Syntheses
..................................... 77
4.2.5.
Carreira s Synthesis of 2a and 2b
........................ 81
4.2.6.
Shibasaki Approach
.................................. 84
4.3.
Syntheses of Epothilone
А/С
(la, 2a)
........................... 87
4.3.1. Fürstners
Alkyne RCM
............................... 87
4.3.2.
Liu Synthesis
....................................... 87
4.3.3.
Panek Approach
..................................... 93
4.3.4.
Wong s
DERA
Approach
............................... 93
4.3.5.
Ley s Approach
..................................... 96
4.4.
Synthesis of Epothilones B/D (lb, 2b)
.......................... 97
4.4.1.
Mulzer Syntheses
.................................... 97
4.4.2.
Grieco s Formal Synthesis of 2b
......................... 101
4.4.3.
White s Syntheses
....................................
J01
4.4.4.
Ermolenko Variation of the White Synthesis
.................. 105
4.4.5.
Synthesis by E. J. Thomas
.............................. 107
4.4.6.
Avery s Synthesis
.................................... 109
4.4.7.
R. E. Taylor s Synthesis
................................
Ill
4.5.
Syntheses of Fragments
.................................... 112
4.5.1.
Kalesse s Synthesis
oí
Nicolaou
s
Intermediates
60
and
82....... 112
4.5.2.
Chandrasekhar s Synthesis of Keto Acid
378
and C7-C16
Fragment
381....................................... 113
4.5.3.
Ramachandran s Synthesis of the MEM-protected
iWť-o/aoM-Aldehyde
(390)............................... 115
4.5.4.
De Brabanders
Synthesis of Aldehyde
63
and Acid
59......... 115
4.5.5.
Wessjohann s Synthesis of Fragments
398
and
401............. 115
4.5.6.
Kulinkovich s Synthesis of Aldehyde
408................... 117
4.5.7. Georgs
Synthesis of Aldehyde
70........................ 117
4.5.8.
Lipase-Catalyzed Synthesis of the C1-C6 Fragment
414......... 118
4.6.
Semisynthetic Degradation/Reconstruction of 2b
................... 118
Contents
VII
4.7.
Syntheses of Epothilones E and
F (le,
Id) and Their
12,13-Deoxy Derivatives (2c, 2d)
.............................. 119
4.7.1.
Nicolaou
s
Synthesis of Id
............................. 119
4.7.2.
Sinha s Synthesis of lc, Id and 2c, 2d
..................... 119
4.8.
Nicolaou s Synthesis of Epothilone Analogues
.................... 119
4.9.
Conclusion and Industrial Application
(ZK
-Еро
(Sagopilone))
.......... 123
Abbreviations
............................................... 125
References
................................................. 126
5.
Semisynthetic Derivatives of Epothilones
K.-H.
Altmann............................................ 135
5.1.
Introduction
............................................. 135
5.2.
The
Оіб-Сб
Sector ( Polyketide Sector )
....................... 137
5.2.1.
Modification of the Ester Moiety
......................... 137
5.2.2.
Modification in the C2-C8 Region
........................ 139
5.3.
Modification of the
Epoxide
Moiety
............................ 141
5.4.
Side Chain Modifications
................................... 146
5.4.1.
Modifications of the C16/C17 Bond and the Thiazole Moiety
..... 146
5.4.2.
Cleavage/Restitution of the
Сіб/СП
Bond
................... 148
5.5.
Removal/Incorporation of the C13-O16 Segment
................... 150
5.6.
Conclusions
............................................. 153
References
................................................. 154
6.
Preclinical Pharmacology and Structure-Activity Studies of Epothilones
K.-H.
Altmann............................................ 157
6.1.
Introduction
............................................. 157
6.2.
In vitro Pharmacology of
Еро В..............................
161
6.3.
In vivo Pharmacology of
Еро В...............................
170
6.4.
Epothilone Analogs and
SAR
Studies
........................... 171
6.4.1.
The
Оіб-Сб
Sector ( Polyketide Sector )
.................. 171
6.4.1.1.
Lactam-based Analogs
.......................... 171
6.4.1.2.
Modifications in the C2-C8 Region
................. 174
6.4.2.
The C9-C13 Sector
( Epoxide
Sector )
.................... 178
6.4.2.1.
Modifications of the C9-C12 Segment
............... 178
6.4.2.2.
Modifications in the
Epoxide
Region (C12/C13)
......... 182
6.4.3.
The C14-C21 Sector
.................................. 191
6.4.3.1.
Side Chain Modifications
......................... 191
6.4.3.2.
C14 Modifications
............................. 205
6.4.4.
Miscellaneous Modifications
............................ 206
6.5.
Structural Studies and Pharmacophore Modeling
................... 206
6.6.
Conclusions
............................................. 209
References
................................................. 210
VIII Contents
7.
Clinical Studies with Epothilones
K.-H.
Altmann............................................ 221
7.1.
Introduction
............................................. 221
7.2.
Patupilone (EPO906,
Еро В).................................
223
7.3.
Ixabepilone
............................................. 224
7.4.
KOS-862
............................................... 228
7.5.
BMS-310705
............................................ 229
7.6.
KOS-1584
.............................................. 230
7.7.
Sagopilone
(ZK
-Еро)
......................................
232
7.8.
ABJ879
............................................... 232
7.9.
Conclusions
............................................. 233
References
................................................. 234
Author Index
.............................................. 239
Subject Index
.............................................. 251
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| id | DE-604.BV035245448 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T21:29:29Z |
| institution | BVB |
| isbn | 9783211782064 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-017051174 |
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| physical | VIII, 260 S. Ill., graph. Darst. |
| publishDate | 2009 |
| publishDateSearch | 2009 |
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| publisher | Springer |
| record_format | marc |
| series2 | Fortschritte der Chemie organischer Naturstoffe |
| spelling | The epothilones an outstanding family of anti-tumor agents ; from soil to the clinic authors: K.-H. Altmann ... Wien [u.a.] Springer 2009 VIII, 260 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Fortschritte der Chemie organischer Naturstoffe 90 Einzelaufnahme eines Zeitschr.-Bd. Antineoplastic agents Antineoplastic agents Effectiveness Epothilone (DE-588)4505296-7 gnd rswk-swf Epothilone (DE-588)4505296-7 s b DE-604 Altmann, Karl-Heinz 1957- Sonstige (DE-588)137117639 oth Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017051174&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | The epothilones an outstanding family of anti-tumor agents ; from soil to the clinic Antineoplastic agents Antineoplastic agents Effectiveness Epothilone (DE-588)4505296-7 gnd |
| subject_GND | (DE-588)4505296-7 |
| title | The epothilones an outstanding family of anti-tumor agents ; from soil to the clinic |
| title_auth | The epothilones an outstanding family of anti-tumor agents ; from soil to the clinic |
| title_exact_search | The epothilones an outstanding family of anti-tumor agents ; from soil to the clinic |
| title_full | The epothilones an outstanding family of anti-tumor agents ; from soil to the clinic authors: K.-H. Altmann ... |
| title_fullStr | The epothilones an outstanding family of anti-tumor agents ; from soil to the clinic authors: K.-H. Altmann ... |
| title_full_unstemmed | The epothilones an outstanding family of anti-tumor agents ; from soil to the clinic authors: K.-H. Altmann ... |
| title_short | The epothilones |
| title_sort | the epothilones an outstanding family of anti tumor agents from soil to the clinic |
| title_sub | an outstanding family of anti-tumor agents ; from soil to the clinic |
| topic | Antineoplastic agents Antineoplastic agents Effectiveness Epothilone (DE-588)4505296-7 gnd |
| topic_facet | Antineoplastic agents Antineoplastic agents Effectiveness Epothilone |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017051174&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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