Part 1 book “Anticancer agents from natural products” has contents: Introduction, camptothecin and its analogs, the discovery and development of the combretastatins, homoharringtonine and related compounds, podophyllotoxins and analogs, the vinca alkaloids, chemistry and biology of the discodermolides, potent mitotic spindle poisons,… and other contents.
ANTICANCER AGENTS from NATURAL PRODUCTS Second Edition Edited by Gordon M Cragg David G.I Kingston David J Newman ANTICANCER AGENTS from NATURAL PRODUCTS Second Edition ANTICANCER AGENTS from NATURAL PRODUCTS Second Edition Edited by Gordon M Cragg David G.I Kingston David J Newman CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2012 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S Government works Version Date: 20110427 International Standard Book Number-13: 978-1-4398-1383-6 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint Except as permitted under U.S Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers For permission to photocopy or use material electronically from this work, please access www.copyright.com (http:// www.copyright.com/) or contact the Copyright Clearance Center, Inc (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400 CCC is a not-for-profit organization that provides licenses and registration for a variety of users For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Preface .ix Editors xi Contributors xiii Chapter Introduction Gordon M Cragg, David G I Kingston, and David J. Newman Chapter Camptothecin and Its Analogs Nicolas J Rahier, Craig J Thomas, and Sidney M Hecht Chapter The Discovery and Development of the Combretastatins 27 Kevin G Pinney, George R Pettit, Mary Lynn Trawick, Christopher Jelinek, and David J Chaplin Chapter Homoharringtonine and Related Compounds 65 Hideji Itokawa, Yukio Hitotsuyanagi, and Kuo-Hsiung Lee Chapter Podophyllotoxins and Analogs 95 Kuo-Hsiung Lee and Zhiyan Xiao Chapter Taxol and Its Analogs 123 David G I Kingston Chapter The Vinca Alkaloids 177 Fanny Roussi, Franỗoise Guộritte, and Jacques Fahy Chapter The Bryostatins 199 David J Newman Chapter The Isolation, Characterization, and Development of a Novel Class of Potent Antimitotic Macrocyclic Depsipeptides: The Cryptophycins 219 Rima S Al-awar and Chuan Shih Chapter 10 Chemistry and Biology of the Discodermolides, Potent Mitotic Spindle Poisons 241 Sarath P Gunasekera and Amy E Wright v vi Contents Chapter 11 The Dolastatins: Novel Antitumor Agents from Dolabella auricularia 263 Erik Flahive and Jayaram Srirangam Chapter 12 Ecteinascidin-743 (Yondelis®), Aplidin®, and Irvalec® 291 Carmen Cuevas, Andrés Francesch, Carlos M Galmarini, Pablo Avilés, and Simon Munt Chapter 13 Discovery of E7389, A Fully Synthetic Macrocyclic Ketone Analog of Halichondrin B 317 Melvin J Yu, Yoshito Kishi, and Bruce A Littlefield Chapter 14 HTI-286 (Taltobulin), A Synthetic Analog of the Antimitotic Natural Product Hemiasterlin 347 Raymond J Andersen, David E Williams, Wendy K. Strangman, and Michel Roberge Chapter 15 The Actinomycins 363 Anthony B Mauger and Helmut Lackner Chapter 16 Anthracyclines 383 Federico-Maria Arcamone Chapter 17 Ansamitocins (Maytansinoids) .407 Tin-Wein Yu, Heinz G Floss, Gordon M Cragg, and David J Newman Chapter 18 Benzoquinone Ansamycins 429 Kenneth M Snader Chapter 19 Bleomycin Group Antitumor Agents 451 Sidney M Hecht Chapter 20 Biochemical and Biological Evaluation of (+)-CC-1065 Analogs and Conjugates with Polyamides 479 Rohtash Kumar and J William Lown Chapter 21 Epothilone, A Myxobacterial Metabolite with Promising Antitumor Activity 513 Gerhard Höfle and Hans Reichenbach Chapter 22 Enediynes 575 Philip R Hamann, Janis Upeslacis, and Donald B Borders vii Contents Chapter 23 The Mitomycins 623 William A Remers Chapter 24 Staurosporines and Structurally Related Indolocarbazoles as Antitumor Agents 647 Michelle Prudhomme Chapter 25 Combinatorial Biosynthesis of Anticancer Natural Products 671 Steven G Van Lanen and Ben Shen Chapter 26 Developments and Future Trends in Anticancer Natural Products Drug Discovery 699 Gordon M Cragg and David J Newman Preface Natural products continue to make new contributions to cancer chemotherapy since the first edition of this volume was published in 2005 These developments include the clinical introductions of cabazitaxel in June 2010 (the first new taxane drug to enter clinical use since docetaxel was introduced in the 1990s), of ixabepilone (the first epothilone analog to enter clinical use), of the marine natural product analog eribulin (which was approved by the FDA in November 2010 for second line therapy in resistant breast cancer), and of the difluorinated vinca alkaloid vinflunine in 2009 In addition, antibody drug conjugates are showing considerable promise in cancer therapy While the enediyne calicheamicin γ 1I was the first antibody-targeted chemotherapeutic agent to be registered for humans, marketed as Mylotarg (gemtuzumab ozogamicin), it has recently been withdrawn from the US market, but SMANCS, a neocarzinostatin conjugate, is approved in Japan for patients with liver cancer metastases Of particular note are antibody-maytansinoid (DM1 and DM4) conjugates, and a biological licence application (BLA, equivalent to the NDA application for small molecules) has been submitted to the FDA by Genentech for marketing approval of one such conjugate, T-DM1 or trastuzumab emtansine, as a treatment for Her2+ breast cancer The chapters in this book have all been substantially revised and updated from those in the first edition In some instances where the original authors were unable to undertake the revision of their chapters, updates by an editor have been included The editors hope that this revised volume will continue to provide examples and inspiration to natural product researchers as well having real value for scientists looking for information on the next generation of anticancer drugs Gordon M Cragg, David G I Kingston, and David J Newman ix ... chapter covering this important natural product Anticancer Agents from Natural Products 10 11 A B 12 13 N C N D 14 18 15 19 O 16 a 16 17 N E O 20 HO O N OH O–Na+ 21 O HO O N HO N N H N O N O HO... 10 11 N Cl Comins's approach HO O HN 12 OH N e Bennasar's approach O 14 15 CO2Et 17 O N CONH2 + 16 MOMO OBn O N O O OEt N2 N OMe O + O 19 Green's [3+2] cycloaddition approach f CO2 Me Br 13 18 ... Products HO N N O N A O A B N DRF -10 42 (39) 10 HO 11 B A B 12 C N D N 18 N O 17 N E O 14 19 HO SN-38 (35) 20 N 21 O N B N Lurtotecan (36) A B N Karenitecin (37) A F B N O D 14 -azaCPT (40) NH2 O A N SiMe3