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INFORMATION to USERS the Most Advanced Technology Has Been Used to Photo­ Graph and Reproduce This Manuscript from the Microfilm Master INFORMATION TO USERS The most advanced technology has been used to photo­ graph and reproduce this manuscript from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are re­ produced by sectioning the original, beginning at the upper left-hand comer and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book. These are also available as one exposure on a standard 35mm slide or as a 17" x 23" black and white photographic print for an additional charge. Photographs included in the original manuscript have been reproduced xerographically in this copy. Higher quality 6" x 9" black and white photographic prints are available for any photographs or illustrations appearing in this copy for an additional charge. Contact UMI directly to order. University Microfilms International A Bell & Howell Information Company 300 North Zeeb Road, Ann Arbor, Ml 48106-1346 USA 313/761-4700 800/521-0600 Order Number 8907201 Synthesis and in vitro studies of radiolabeled and fluorescent aromatase inhibitors Chen, Hsiu-Ho, Ph.D. The Ohio State University, 1988 UMI 300 N. Zeeb Rd. Ann Arbor, MI 48106 SYNTHESIS AND IN VITRO STUDIES OF RADIOLABELED AND FLUORESCENT AROMATASE INHIBITORS DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Hsiu-Ho Chen, M.S. a je s f c The Ohio State University 1988 Dissertation Committee: Approved by Robert W. Brueggemeier, Ph.D. Dennis R. Feller, Ph.D. Duane D. Miller, Ph.D. Larry W. Robertson, Ph.D. c / m ~—* Robert W. Brueggemeier College of Pharmacy DEDICATION To Dad and Mom - ii - ACKNOWLEDGEMENTS I am grateful to acknowledge the following individuals and organiza­ tions for their assistance in the completion of my graduate studies: To professor Robert W. Brueggemeier for all his guidance, concern and insight throughout my stay at the university. To Chung-Shan Institute of Science and Technology, R.O.C. for full fellowship support till dissertation completion date. To all faculty, staff and my fellow graduate students for their friendship, support and valuable suggestions. To Mr. J. Fowble, Mr. J. Miller, Mr. R. Weisenberger and Mr. D. Chang for their help in obtaining Mass, NMR and FTIR spectra. To Dr. Michael Darby and Miss Nancy Katlic for their technical assistance in preparing radiolabeled compound and MCF-7 cell cultures. To Mr. Paul Campbell for his great assistance in preparing this document on the College's computer equipment. Lastly and most importantly, to my parents and husband for their love, understanding and enthusiastic support. - ill - VITA May 12, 1953................ Born - Taipei, Taiwan, R.O.C. June, 1976 .................. B.S. Pharmacy, Taipei Medical College. August, 1978 ................ M.S. Pharmaceutical Chemistry, National Defense Medical Center(NDMC). Sept. 1979-Aug. 1984 ......... Instructor, School of Pharmacy, NDMC. Sept. 1984-present .......... Graduate Student, College of Pharmacy, The Ohio State University. PUBLICATIONS Articles: 1. H.H. Chen, "Synthesis and Biological Evaluation of Perimidine Derivatives", M.S. Thesis, NDMC, 1978. 2. K.C. Liu und H.H. Chen, "Synthese und anorektishe wirkung einiger kondensierter Perimidin-Derivate", (1979) Arch. Pharm. (Weinheim), 312, 776-780. 3. K.C. H u and H.H. Chen,"Synthesis of Mannich Bases of 5-Methyl -lH-benzotriazole as Potential Muscle Relaxants", (1981) J.Taiwan Pharm. Ass. 33, 61-66. 4. K.C. Liu and H.H. Chen, "Synthesis of Mannich Bases of 5-Nitro lH-benzotriazole as Potential Muscle Relaxants", (1982) J. Taiwan Pharm. Ass. 34, 108-113. 5. K.C. Liu und H.H. Chen, "Synthese und Anorekitishe Prufung von Thiazole [3,2-a] Perimidin” , (1983) Arch. Pharm. (Weinheim) 316, 728-729. - iv - 6. K.C. Liu and H.H. Chen, "Reaction of 2-Hydrazinoperimidine with Acetylacetone", (1984) J. Heterocycl. Chem. 211, 911-912. 7. K.C. Liu and H.H. Chen, "Synthesis and Anorectic Evaluation of per- imidone, 2-Azaperimidine and 2,3-Dihydroperimidine- 2-spirocyclhexane", (1984) J. Taiwan Pharm. Ass. 36, 140-143. 8. K.C. Liu and H.H. Chen, "Cyclocondensation of 2-Hydrazino- perimi- dine with Diethyl oxalate and Ethyl pyruvate", (1985) J. Hetero- cycl. Chem. 22, 1363-1364. 9. K.C. H u and H.H. Chen, "Syntheses of 3-Substituted 1H-1,2,4- Tria- zolo [4,3-a] Perimidine", (1985) Arch. Pharm. (Weiheim) 318, 468-470. Abstracts and Presentations: 1. K.C. Liu and H.H. Chen, "Synthesis and Biological Evaluation of Perimidine Derivatives", 9th International Heterocyclic Chemistry Congress, Tokyo, Japan, August 22-26, 1983. 2. P.K. Li, H.H. Chen, N.E. Katlic, M.V. Darby, and R.tf. Brueggemeier "7a-Substituted Steroidal Aromatase Inhibitors in Hormone-dependent Breast Cancer in Culture and in Vivo", International Conference on Aromatase, Miami, Florida, March 4-7, 1987. Abstract No. 23. 3. R.W. Brueggemeier, N.E. Katlic, P.K. Li, H.H. Chen, and M.V. Darby, "7a-Substituted Steroidal Aromatase Inhibitors in Hormone-dependent Breast Cancer in Culture and In Vivo". 193rd ACS National Meeting, Denver, Colorado, April 5-10, 1987. Abstract No. 50. FIELD OF STUDY Major Field: Medicinal Chemistry Steroid Biochemistry - v - TABLE OF CONTENTS PAGE DEDICATION................................................................................................................. ii ACKNOWLEDGMENTS................................................................................................. iii VITA............................................................................................................................. iv LIST OF FIGURES................................................................................................,. ix LIST OF TABLES................................................................................................... xii LIST OF SCHEMES............................................................................................... xiii ABBREVIATIONS................................................................................................... xiv CHAPTER I. INTRODUCTION............................................................................. 1 1.1. The role of aromatase in estrogen biosynthesis ............................ 2 1.1.1. Estrogen biosynthesis in the ovary ............................ 3 1.1.2. Estrogen biosynthesis in the placenta ........................ 6 1.1.3. Extragonadal aromatization ............................................ 8 1.1.4. Mechanisms of aromatization .......................................... 10 1.1.5. Purification and characteristics of aromatase 14 1.2. Classification of aromatase inhibitors ............................................ 17 1.2.1. Steroidal aromatase inhibitors ...................................... 18 1.2.1.1. A-ring modifications ........................................ 19 1.2.1.2. Cjg substitutions .............................................. 23 1.2.1.3. B-ring modifications ........................................ 32 1.2.1.4. D-ring modifications ........................................ 37 - vi - 1.2.2. Nonsteroidal aromatase inhibitors ................................. 40 1.3. Metabolism of aromatase inhibitors ................................................... 45 CHAPTER II. STATEMENT OF OBJECTIVES............................................... 49 2.1. Synthesis of radiolabeled aromatase inhibitors ........................... 50 2.2. Synthesis of fluorescent aromatase inhibitors ............................. 52 2.3. Synthesis of the mechanism-based inhibitors ................................. 53 Summary....................................................................................................... 54 CHAPTER IH. EXPERIMENTAL....................................................................... 59 3.1. Synthetic methods ..................................................................................... 61 3.2. Biochemical methods ................................................................................. 75 3.2.1. Studies on placental microsomes ..................................... 75 3.2.1.1. Competitive inhibition studies for inhibitors 49-57 ............................................... 76 3.2.1.2. Time-dependent aromatase inactivation studies for inhibitors 54, 55 and 57 ___ 76 3.2.1.3. Aromatase irreversible inactivation by inhibitors 54, 55 and 57 ................................. 77 3.2.1.4. Preliminary stability studies for I-IPTA metabolism ...................................... 78 3.2.1.5. Time course for •^I-IPTA metabolism... 79 3.2.1.6. Various protein concentrations for I-IPTA metabolism ...................................... 80 3.2.1.7. Various concentrations of IPTA at constant protein concentration metabolism ......................................................
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