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Development of Isoflavonoid-Derived Anti-Prostatic Cancer Agents University of Wollongong Research Online University of Wollongong Thesis Collection 1954-2016 University of Wollongong Thesis Collections 2005 Development of isoflavonoid-derived anti-prostatic cancer agents Jane Eliza Faragalla University of Wollongong Follow this and additional works at: https://ro.uow.edu.au/theses University of Wollongong Copyright Warning You may print or download ONE copy of this document for the purpose of your own research or study. The University does not authorise you to copy, communicate or otherwise make available electronically to any other person any copyright material contained on this site. You are reminded of the following: This work is copyright. Apart from any use permitted under the Copyright Act 1968, no part of this work may be reproduced by any process, nor may any other exclusive right be exercised, without the permission of the author. Copyright owners are entitled to take legal action against persons who infringe their copyright. A reproduction of material that is protected by copyright may be a copyright infringement. A court may impose penalties and award damages in relation to offences and infringements relating to copyright material. Higher penalties may apply, and higher damages may be awarded, for offences and infringements involving the conversion of material into digital or electronic form. Unless otherwise indicated, the views expressed in this thesis are those of the author and do not necessarily represent the views of the University of Wollongong. Recommended Citation Faragalla, Jane Eliza, Development of isoflavonoid-derived anti-prostatic cancer agents, PhD thesis, Department of Chemistry, University of Wollongong, 2005. http://ro.uow.edu.au/theses/597 Research Online is the open access institutional repository for the University of Wollongong. For further information contact the UOW Library: [email protected] 1 Development of Isoflavonoid-Derived Anti-Prostatic Cancer Agents A thesis in fulfilment of the requirements for the award of the degree Doctor of Philosophy from the University of Wollongong By Jane Eliza Faragalla, B Med. Chem. (hons) University of Wollongong Department of Chemistry Wollongong, Australia May, 2005 ii Certification I, Jane Eliza Faragalla, declare that this thesis, submitted in fulfillment of the requirements for the award of Doctor of Philosophy, in the Department of Chemistry, University of Wollongong, is wholly my own work unless other referenced or acknowledged. The document has not been submitted for qualifications at any other academic institution. Jane Faraglla 6th May, 2005. iii Table of Contents Acknowledgements .................................................................................................................................... vi List of Publications Arising from this Work. ........................................................................................ viii List of Figures ............................................................................................................................................ ix List of Schemes ........................................................................................................................................ xiii List of Tables .......................................................................................................................................... xvii Abreviations ........................................................................................................................................... xviii Abstract .................................................................................................................................................. xxiv CHAPTER 1 INTRODUCTION ....................................................................... 2 1.1 Prostate Cancer ........................................................................................................................... 2 1.2 What is the Prostate? .................................................................................................................. 3 1.2.1 Benign Prostatic Hyperplasia .................................................................................................... 3 1.3 What is Cancer? ........................................................................................................................... 4 1.3.1 General ..................................................................................................................................... 4 1.3.2 Cell Cycle .................................................................................................................................. 5 1.3.3 Cell Cycle Regulation and How Cancer Cells Escape Regulation ............................................ 6 1.3.4 COX-2 ....................................................................................................................................... 8 1.3.5 Metastasising Mechanisms ........................................................................................................ 8 1.4 Prostate Cancer Development ..................................................................................................... 9 1.5 Factors Influencing Cancer Development ............................................................................... 11 1.5.1 Genetics, Familial and Racial Differences .............................................................................. 11 1.5.2 Diet .......................................................................................................................................... 12 1.6 Cancer Drug Targets ................................................................................................................. 14 1.6.1 Hormonal Regulation of Androgens ....................................................................................... 14 1.7 Current (Prostate) Cancer Drugs ............................................................................................. 17 1.7.1 Androgen Ablation .................................................................................................................. 17 1.7.2 Cytotoxic Agents ..................................................................................................................... 21 1.8 Benzopyrans ............................................................................................................................... 26 1.9 Phenoxodiol ................................................................................................................................ 29 1.10 Aims ............................................................................................................................................ 31 iv CHAPTER 2 MOLECULAR MODELING, PHARMACOPHORE .. 34 DEVELOPMENT AND TARGET DESIGN ....................................................... 34 2.1 Introduction ................................................................................................................................ 34 2.1.1 Selection of Training Set Molecules for 5-α-Reductase Pharmacophores .............................. 35 2.1.2 Conformer Generation .............................................................................................................. 38 2.1.3 Pharmacophore Generation ..................................................................................................... 38 2.2 RESULTS AND DISCUSSION: ............................................................. 41 2.2.1 Hypothesis Analysis ................................................................................................................ 45 2.2.2 Hypothesis Assessment by Flavonoids, Indoles and Naphthalene Inhibitors ......................... 58 2.2.3 Assessment of Novogen’s Isoflavonoids on 5AR Pharmacophores and Design of Synthetic Targets 65 1.1.1. Compound ............................................................................................................................... 66 2.2.4 Design of New Targets ............................................................................................................ 69 2.2.5 Target Compounds which Incorporate the 5AR and α1A Moieties ......................................... 73 2.3 Summary and Conclusions ....................................................................................................... 73 CHAPTER 3 SUBSTITUTION REACTIONS AT THE 2-POSITION ........ 76 OF ISOFLAVENES ........................................................................................... 76 3.1 Introduction ............................................................................................................................... 76 3.2 General Synthetic Approaches .......................................................................................................... 80 3.2.1 2-Substituted-2H-Benzopyran Synthesis via Ring Closure through O1-C2 Bond Formation 80 3.2.2 2-Substituted 2H-1-Benzopyran Synthesis through Ring Closure by C3-C4 Bond Formation 84 3.2.3 Synthesis of 2-Substituted Isoflavenes through Benzopyrylium-Based Approaches .............. 85 3.2.4 Synthetic Proposal for the 2-Substituted Isoflavene Derivatives ............................................ 88 3.3 Results and Discussion .............................................................................................................. 90 3.3.1 Synthesis of Phenol-Protected Isoflavenes .............................................................................. 90 3.3.2 Synthesis of a Boc
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