ACCA CHEMISTRY COURSE
Medicinal Chemistry
Fall 2001
Course #: Topics: 494 A/B - ACCA Seminar or 03-498-1
September 11-November 13, 2001
Credit: 1 or 2 semester hours
 
Instructor: Dr. Salim M. Diab
Office: Room 215, St. Albert
Phone: 815-740-3855 (Ext. 3855)
Home Phone: 815-730-8302
E-mail: sdiab@stfrancis.edu
homepage:http://www.stfrancis.edu/ns/diab/etherman.htm

The course is held at the Morton Arboretum (Hwy 53) near Lyle, from 7:00-9:00 PM on Tuesday evenings.

Coordinators:
Douglas Armstrong, Olivet Nazarene University, Phone 815-939-5393, FAX 815-939-5071, darmstrg@olivet.edu
Salim M. Diab, University of St. Francis, Phone 815-740-3855, FAX 815-740-4285, SDiab@stfrancis.edu
Brent Friesen, Dominican University, jbfriesen@email.dom.edu

Schedule of topics, dates, and speakers:
Date                 Topic                                                  Speaker



Sept. 11     Introduction to Principles        Dr. Robin M. Zavod and Dr.
                  of Medicinal Chemistry            Shridhar Andurkar, Chicago
                                                                    College of Pharmacy

Sept. 18     SAR by NMR: Discovering     Dr. Philip Hajduk, Abbott
                   High-Affinity Ligands for          Laboratories
                   Proteins

Sept. 25      Discovering New Drugs from  Dr. Doel Soejarto, College of
                   the Tropical Rain Forests in     Pharmacy, University of
                   the 21st Century: The UIC       Illinois at Chicago
                   ICBG Model

Oct. 2         A Molecular Tour into the         Dr. Jean Chmielewski, Purdue
                   Design of HIV Therapeutics     University
 

Oct. 9         1. Utility of Fluorine in Biologically   Dr. James McCarthy, Eli Lilly
                   Active Molecules, AND 2. The
                   Design and Synthesis of
                   Tezaciltabilne, a Mechanism-
                   Based Inhibitor of Ribonucleo-
                   tide Reductase

Oct. 16       Strategic Approaches for the        Dr. Steve Jacobsen,
                   Treatment of Alzheimer's              American Home Products,
                   Disease                                        Wyeth-Ayerst Research

Oct. 23       Effects of P-Glycoproteins (P-gp) efflux on the brain deposition of two structurally related
                   neurokenin 1 (NK1) antagonists - by F. David Tingley III, Pfizer Global Research and Development,
                   Pfizer, Inc.

                   Antimicrobacterial Agents for treatment of Tuberculosis and leprosy - by Dr. Scott G. Franzblau, Director,
                   Institute For Tuberculosis Research, College of Pharmacy, UIC.

Oct. 30       Structure-based Drug Design       Dr. Jonathan Greer, Abbott
                   in Drug Discovery                         Laboratories

                   Combinatorial Chemistry in the      Dr. Thomas J. Sowin,
                   Drug Discovery Process               Abbott Laboratories

Nov. 6        Radiopharmaceutical Chemistry:   Dr. Susan  Z. Lever, MU
                   The Basics                                    Research Reactor, Univ.
                                                                         of Missouri-Columbia

Nov. 13      The Role of Plants in Drug            Dr. Geoffrey A. Cordell,
                   Discovery: Past, Present, and       College of Pharmacy, Univ.
                   Future                                            of Illinois at Chicago

Required Texts:
None

References:

Journals
The following journals may be helpful to students taking this course.
1. Current Opinion in Pharmacology, a new (2001) review journal published by Elsevier Science London.
2. Journal of Ethnopharmacology, edited by Dr.  Doel Soejarto.
3. Journal of Medicinal Chemistry, published by the American Chemical Society.
4. Journal of Medicinal Food, published by Mary Ann Liebert, Inc.
5. Journal of Natural Products, published by the American Chemical Society and the American Society of Pharmacognosy.
6. Journal of Organic Chemistry, published by the American Chemical Society.
7. Modern Drug Discovery, published by the American Chemical Society.
8. Molecular Pharmacology, published by the American Society of Pharmacology and Experimental Therapeutics.  (molpharm.aspetjournals.org)
9. Natural Product Reports, published by The Royal Society of Chemistry, London, England.
10. Pharmaceutical Biology (formerly entitled International Journal of Pharmacognosy).
11. Phytomedicine, published by Gustav Fischer Verlag, Stuttgart, Jena, New York.
12. Trends in Pharmacological Sciences.

Specific Journal Articles
Listed below are just a few specific journal articles, which may be of interest to students taking this course.
1. Trends in Pharmacological Sciences.  For a review on pharmacologically active marine natural products, see 1995, 16: 275-279.
2. "Chiral Drugs," Chemical and Engineering News, October 23, 2000, pp.  55 ff.
3. "Chiral Chemistry," ibid., May 14, 2001, pp.  45 ff.
4. "Structure - Based Drug Design," ibid, June 4, 2001, pp.  69 ff.
5. "Buzzing About Potential Antimalarials," Modern Drug Discovery, June, 2000, p.  13.

Books
The following books may be helpful to the students taking this course.  They are listed alphabetically by the last name of the (first) author or editor.
1. "Supercritical Fluids: Extraction and Pollution Prevention," Edited by Martin A. Abraham and Aydin A. Sunol, 1997, American Chemical Society, ACS Symposium Series No. 670.  This book includes supercritical fluid extraction of natural products.
2. "Selective Toxicity: The Physico-chemical Basis of Therapy," Seventh Edition, Adrien Albert, 1985, Chapman and Hall (London), ISBN 0-412-26010-7.
3. "Xenobiosis: Foods, Drugs, and Poisons in the Human Body," Adrien Albert, 1987, Chapman and Hall (London), ISBN 0-412-28800-1 or 0-412-28810-9 (paperback).
4. "Drug Handbook -- A Nursing Process Approach," Rosalinda Alfaro - LeFevre, Marcia E. Blicharz, Nancy M. Flynn, and Mary Jo Boyer, 1992, Addison-Wesley Nursing, ISBN 0-201-09278-6.
5. "Plants, People, and Culture: The Science of Ethnobotany," Michael J.  Balick and Paul Alan Cox, 1997, Published by Scientific American Library, Distributed by W.H. Freeman and Company, ISBN 1040-3213.
6. "Comprehensive Natural Products Chemistry," Editors -In-Chief, D.H.R. Barton and K.  Nakanishi; Executive Editor, O.  Meth-Cohn, 1999, Elsevier Science, ISBN 0-08-042709-X.  This is a set consisting of the following volumes:
 Volume 1: "Polyketides and Other Secondary Metabolites Including Fatty Acids and Their Derivatives."
 Volume 2: "Isprenoids Including Carotenoids, and Steroids."
 Volume 3: "Carbohydrates and their Derivatives Including Tannins, Cellulose, and   Related Lignins."
 Volume 4: "Amino Acids, Peptides, Porphyrins and Alkaloids."
 Volume 5: "Enzymes, Enzyme Mechanisms, Proteins, and Aspects of NO Chemistry."
 Volume 6: "Prebiotic Chemistry, Molecular Fossils, Nucleosides and RNA."
 Volume 7: "DNA and Aspects of Molecular Biology."
 Volume 8: "Miscellaneous Natural Products."
7. "Nuclear Medicine Technology and Techniques," Third Edition, Edited by Bernier, Christian, and Langan, 1994, Mosby, ISBN 0-8016-7060-8.
8. "Human Pharmacology," Second Edition, Theodore M. Brody, et al., 1994, Mosby, ISBN 0-8016-7928-1.
9. "Pharmacognosy, Phytochemistry, Medicinal Plants," Jean Bruneton, 1995, Springer-Verlag, ISBN 1-898298-13-0.
10. "Pharmacology for Chemists," Joseph G.  Cannon, 1999, American Chemical Society, ISBN 0-8412-3524-4.
11. "Radiochemistry and Nuclear Chemistry," Second Edition, G. Choppin, J. Rydberg, and J.O. Liljenzin, Butterworth Heimann, Ltd., 1995.
12. "Cutting's Handbook of Pharmacology," Seventh Edition, T.Z. Csaky and Byron A. Barnes, 1984, Appleton-Century-Crofts, ISBN 0-8385-1418-9.  (NOTE: This book is out-of-print, so students will not be able to purchase it, but might find it in a library.  Also, a more recent name for this publisher is Appleton-Lange.)  13. "Medicinal Chemistry Case Study Workbook," Bruce Currie, Victoria F. Roche, and S. William Zito, 1996, Williams and Wilkins, ISBN 0-683-02260-1.  As a case study, this book poses various patient scenarios (i.e., patient has ____ symptoms, or ____ disease, or ____ condition) and considers what should be done.  As such, this book represents an approach in which the emphasis is placed on the patient, not on the drugs.
14. "Natural Products Medicine: A Scientific Guide to Foods/Drugs/Cosmetics," Ara Der Marderosian and Lawrence E. Liberti, 1988, George F. Stickley Company, ISBN 0-89313-099-0.
15. "High Throughput Screening: The Discovery of Bioactive Substances," John P. Devlin, 1997, Dekker, ISBN 0-8247-0067-8.
16. "Medicinal Natural Products: A Biosynthetic Approach," Paul M. Dewick, Wiley, 1997, ISBN 0-471-97478-1.
17. "Handbook of Medicinal Herbs," James A. Duke, 1987, CRC Press, ISBN 0-8493-3630-9.  This handbook catalogs 365 species of herbs having medicinal or folk medicinal uses.  Plants from all over the world, from common cultivars to rare species, are included.
18. "Handbook of Edible Weeds," James A. Duke, 1992, CRC Press, ISBN 0-8493-4225-2.  Although this book contains cautionary notes regarding the potential allergenic or other harmful properties of many of the weeds, it emphasizes finding practical uses for weeds, rather than waging pesticidal war on them.
19. "Amazonian Ethnobotanical Dictionary," Edited by James Alan Duke and Rodolfo Vasquez Martinez, 1994, CRC Press, ISBN 0-8493-3664-3.  This book was designed and conceived in the rainforest and is dedicated to its preservation.  Although this book places emphasis on plant foods and rainforest medicines, there is also commentary on other relevant applications, including natural pesticides.  Dr. Richard E. Schultes, Botanical Museum of Harvard University, internationally respected authority in this area, commented about this book in Environmental Conservation as follows: "We have waited a long time for this kind of listing of the natively employed plants of the Amazonia.  Here it is!  And it will certainly be a most useful compendium for every botanist, ethnobotanist, and anthropologist who is working or intends to work in this most wonderful part of the world..."
20. "Principles and Practice of Nuclear Medicine," Second Edition, Edited by P.J. Early and D. B. Sodee, 1995, Mosby, ISBN 0-8016-2577-7.
21. "Radiochemistry and Nuclear Methods of Analysis," William D. Ehmann and Diane E. Vance, John Wiley and Sons, Inc., 1991.
22. "Trease and Evans Pharmacognosy," 14 th Edition, Evans, 1996, Saunders, ISBN 0-7020-1899-6.
23. "Principles of Medicinal Chemistry," Fourth Edition, William O. Foye, Thomas L. Lemke, and David A. Williams, Editors, 1995, Williams and Wilkins, ISBN 0683033239.
24. "Medicinal Chemistry: The Role of Organic Chemistry in Drug Research," Second Edition, C.R. Ganellin and S.M. Roberts, Editors, 1993, Academic Press, ISBN 0-12-274120-X.
25. "Phytochemical Diversity: A Source of New Industrial Products," Edited by M. Hayes, et al., 1997, The Royal Society of Chemistry, Special Publication No. 200.
26. "Essentials of Nuclear Medicine Science," Edited by William Hladik, III, Gopal Saha, and Kenneth Study, 1987, Williams and Wilkins, ISBN 0-683-04051-0.
27. "A Dictionary of Natural Products: Terms in the Field of Pharmacognosy Relating to Natural Medicinal and Pharmaceutical Materials and the Plants, Animals, and Minerals from Which They Are Derived," George M. Hocking, 1997, Plexus, ISBN 0-937548-31-6.
28. "Handbook of African Medicinal Plants," Maurice M. Iwu, 1993, CRC Press, ISBN 0-8493-4266-X.
29. "Methods of Genome Analysis in Plants," Edited by Prem P. Jauhar, 1995, CRC Press, ISBN 0-8493-9437-6.
30. "Earthly Goods: Medicine-Hunting in the Rainforest," Christopher Joyce, 1994, Little, ISBN 0-316-47408-8.
31. "Handbook of Ayurvedic Medicinal Plants," Edited by L.D. Kapoor, 1990, CRC Press, ISBN 0-8493-0559-4.
32. "Basic and Clinical Pharmacology," Eighth Edition, Edited by Bertram G.  Katzung, 2001, Lange Medical Books/McGraw-Hill, ISBN 0-8385-0598-8.
33. "Medicinal Chemistry: Principles and Practice," Frank D. King, Editor, 1994, CRC Press, ISBN 0851864945.
34. "Human Medicinal Agents from Plants," Edited by A. Douglas Kinghorn and Manual F. Balandrin, American Chemical Society Symposium Series 534, 1993, published by the American Chemical Society, Washington, D.C., ISBN 0-8412-2705-5.
35. "Essentials of Medicinal Chemistry," Second Edition, Andrejus Korolkovas, 1988, Wiley, ISBN 0-471-88356-5.
36. "Essentials of Molecular Pharmacology: Background for Drug Design," Andrejus Korolkovas, Reprint Edition, Books on Demand, Division of University Microfilms International, Ann Arbor, MI, ISBN 0-317-07906-9.
37. "Radiopharmaceuticals in Nuclear Medicine Practice," Richard Kowalsky and J. Randolph Perry, 1987, Appleton and Lange, ISBN 0-8385-8263-X.
38. "Phytomedicines of Europe: Chemistry and Biological Activity," edited by Larry D. Lawson and Rudolf Bauer, 1998, American Chemical Society, ACS Symposium Series No. 691.
39. "Review of Organic Functional Groups: Introduction to Medicinal Organic Chemistry," Third Edition, Thomas L. Lemke, 1992, Lea and Febiger, ISBN 0-812-11428-0.
40. "Drugs and the Human Body -- With Implications for Society," Fourth Edition, Ken Liska, 1994, Macmillian, ISBN 0-02-371091-8.
41. "Designing Bioactive Molecules: Three-Dimensional Techniques and Applications," Edited by Yvonne Connolly Martin and Peter Willett, 1998, American Chemical Society, ACS Professional Reference Books.
42. "Drug Actions, Basic Principles, Therapeutic Aspects," Ernst Mutschler, et al., 1995, CRC Press, ISBN 0-8493-7774-9.
43. "Topics in Medicinal Chemistry: A Comprehensive Text for Students and Practitioners in Health Sciences," Jay Nematollahi, 1983, Scientific Service, No ISBN given.
44. "Medicinal Chemistry: A Biochemical Approach," Second Edition, Thomas Nogrady, 1988, Oxford University Press, ISBN 0-19-505368-0 or 0-19-505369-9 for paperback.
45. "An Introduction to Medicinal Chemistry," Graham L. Patrick, 1995, Oxford University Press, ISBN 0198558724 or 0198558716 for paperback.
46. "Anticancer Drugs from Animals, Plants, and Microorganisms," George R. Pettit, et al., 1994, Wiley, ISBN 0-471-03657-9.
47. "Medicine Quest: In Search of Nature's Healing Secrets," Mark J.  Plotkin, 2000, Viking, ISBN 0-670-86937-6.
48. "Shaman's Apprentice," Mark J. Plotkin and Lynne Cherry, 1998, HarBrace, ISBN 0-15-201281-8.
49. "Pharmacology," Third Edition, H.P. Rang and Gardner, 1995,  Churchill Livingstone, ISBN 0-443-07560-3.
50. "Pharmacology and Toxicology of Naturally Occurring Toxins," Edited by H. Raskova, 1971, Pergamon Repr. UK, Franklin, ISBN 0-08-016797-7.
51. "Spices: Flavor Chemistry and Antioxidant Properties," Edited by Sara J. Risch and Chi-Tang Ho, 1997, American Chemical Society, ACS Symposium Series 660.
52. "Pharmacognosy and Pharmacobiotechnology," Robbers, Speedie, and Tyler, 1996, Williams and Wilkins, ISBN 0-683-08500-X.  This book was written as a revision of the Ninth Edition of "Pharmacognosy," by Tyler, Brady, and Robbers (see elsewhere in this list), but since it has a different title, it is not the Tenth Edition.
53. "Natural and Synthetic Organic Medicinal Compounds," O. LeRoy Salerni, 1976, Mosby, ISBN 0-8016-4303-1.  (Apparently this book is out-of-print, so students will not be able to purchase it, but might find it in a library.)
54. "Top Drugs * Top Synthetic Routes," John Saunders, 2000, Oxford University Press, ISBN  850100-5.
55. "The Organic Chemistry of Drug Design and Drug Action," Richard B. Silverman, 1992, Academic Press, ISBN 0-12-643730-0.  Dr. Timothy Wilkinson used parts of this book in a medicinal chemistry course he taught at Wheaton College.
56. "Flavours and Fragrances," Edited by K. Swift, 1998, The Royal Society of Chemistry, Special Publication No. 214.
57. "Nursing Pharmacology -- An Integrated Approach to Drug Therapy and Nursing Practice," Second Edition, Alvin K. Swonger and Myrtle P. Matejski, 1991, Lippincott, ISBN 0-397-54854-0.
58. "Chinese Drugs of Plant Origin: Chemistry, Pharmacology, and Use in Traditional and Modern Medicine," W. Tang and G. Eisenbrand, 1992, Springer-Verlag, ISBN 0-387-19309-X.
59. "Recent Developments in Flavour Science," Edited by A. Taylor and D.S. Mottram, 1997, The Royal Society of Chemistry.
60. "Introductory Medicinal Chemistry," Second Edition, J.B. Taylor and P.D. Kennewell, 1990, Prentice-Hall (United Kingdom), ISBN 0134988906.
61. "Bioactive Compounds from Marine Organisms: With Emphasis on the Indian Ocean," Indo-United States Symposium, Edited by Mary-Frances Thompson, et al., 1991, Published by A.A. Balkema NE, Ashgate Publishing Co., ISBN 90-6191-929-0.
62. "The Cross Name Index to Medicinal Plants," Anthony R. Torkelson, 1995, CRC Press.  International in scope, this is a three-volume set, providing over 4,000 scientific names, cross-indexed to more than 28,000 common names of medicinal plants.  The first volume is organized alphabetically by scientific name, whereas the other two volumes are a cross index by common name.
 ISBN for Volume 1: 0-849326311.
 ISBN for Volume 2: 0-84932632X.
 ISBN for Volume 3: 0-849326338.
 ISBN for the whole set: 0-849326354.
63. "Hoosier Home Remedies," Varro E. Tyler, 1985, Purdue University Press, ISBN 0-911198-77-6; paperback 0-911198-83-0.
64. "Honest Herbal:  A Sensible Guide to the Use of Herbs and Related Remedies," Third Edition, Varro E. Tyler, 1993, Haworth Press, ISBN 1-56024-286-8; paperback 1-56024-287-6.
65. "Herbs of Choice:  The Therapeutic Use of Phytomedicinals," Varro E. Tyler, 1994, Haworth Press, ISBN 1-56024-894-7; paperback 1-56024-895-5.
66. "Pharmacognosy," Ninth Edition, Tyler, Brady, and Robbers, 1988, Lea and Febiger. ISBN 0-8121-11071-4.
67. "Principles of Nuclear Medicine," Second Edition, Edited by Wagner, Szabo, and Buchanan, 1995, W. B. Saunders, ISBN 0-7216-9091-2.
68. "Economic and Medicinal Plant Research," Volume 6, Edited by H. Wagner and Norman R. Farnsworth, 1994, Academic Press, ISBN 0-12-730067-8.  (There are also several other volumes.)
69. "The Practice of Medicinal Chemistry," Edited by Camille Georges Wermuth, 1996, Academic Press, ISBN 0-12-744640-0.
70. "Herbal Drugs and Phytopharmaceuticals," Edited by Max Wichtl, English edition translated and edited by Norman Grainger Bisset, 1995, CRC Press, ISBN 0-8493-7192-9.
71. "Textbook of Organic Medicinal and Pharmaceutical Chemistry," Ninth Edition, Charles O. Wilson and Ole Gisvold, 1991, Lippincott, ISBN 0-397-50877-8.
72. "Burger's Medicinal Chemistry and Drug Discovery," Fifth Edition, Volume 2 -- "Therapeutic Agents," Manfred Wolff, Editor, 1996, Wiley, ISBN 0-471-575577.
73. "Burger's Medicinal Chemistry and Drug Discovery," Fifth Edition, Volume 1 -- "Principles and Practice," Manfred Wolff, Editor, 1994, Wiley, ISBN 0-471-575569.
74. "An Illustrated Chinese Materia Medica," Jing-Nuan Wu, 2001, ISBN 0-19-514017-6.

Publications Other than Journals and Books
The following items are very noteworthy, but do not fit into the categories (journals, books) above.
1. "Annual Reports in Medicinal Chemistry," Volume 35, 2000, Academic Press.  See also earlier volumes, one per year, back to 1965.
2. "Advances in Medicinal Chemistry," started in 1992, published by JAI Press.
3. "Progress in Medicinal Chemistry," started in 1961, published by North-Holland Publishing Company and American Elsevier.
4. "The Pharmaceutical Century * Ten Decades of Drug Discovery."  Supplement to ACS Publications, 2000.

Web Links:
http://wings.buffalo.edu/academic/department/pharmacy/mch/public_html/informatic.html
http://www.weber.edu/ewalker/Medicinal_Chemistry/topoutline.htm
http://www.phc.vcu.edu/links.html
http://www.phc.vcu.edu/link/courses.html
http://pubs.acs.org/journals/jmcmar/index.html
http://www.chem.qmw.ac.uk/iupac/medchem/
http://www.aaps.org/
http://157.142.72.77/pharmacy/pharmint.html
http://www.rxlist.com/
http://monomerchem.com/display4.html
http://www.pharm.uu.nl/onderzk/medchem.html
http://dwb.unl.edu/Teacher/NSF/C01/C01Links/www.netaccess.on.ca/~dbc/cic_hamilton/med.html
http://members.tripod.com/~ChristopherMarrs/MedicinalChemistry.html
http://www.apnet.com/chemistry/journals.html
http://www.tripos.com/research/medchem.html

Expectations of Students:
1. Attendance is required. If you need to miss a lecture, please let me know and we will work out a substitute assignment.
2. A feedback form is required for each speaker. The form will be distributed on the day of the presentation and must be turned in to your instructor the following week.
3. Active participation is encouraged. This can be done in the form of questions, comments, or informal dialogue with the speakers and other participants.
 

Criteria for Evaluation
One-hour credit: attend all lectures and submit a written summary/critique of each lecture.

Two-hour credit: 50% of the grade will be based on the same criteria as the one-hour credit. The other 50% will be based on a research paper on one of the topics discussed in the course. The paper must be 8-10 pages, well researched, properly cited with all the relevant bibliography.