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Fundamentals of Chemistry of Biologically Active Substances

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Fundamentals of Chemistry of Biologically Active Substances Kazan State University A.M. Butlerov Institute for Chemistry Irina Galkina FUNDAMENTALS OF CHEMISTRY OF BIOLOGICALLY ACTIVE SUBSTANCES Training manual for students of colleges and universities. (Compendium of the lecture course) «Approved by the training department for classical higher education as a learning aid for students of the major 020101.65 Chemistry» Kazan – 2006 2 УДК 544 ББК 24 Publication approved by the training center of the A.M. Butlerov Institute for Chemistry of Kazan State University. Author: Galkina I.V. – Cand. Chi. Sci., docent of chemical faculty of KSU.. Reviewer: Terenin I.V. – Doctor Chi. Sci., professor of chemical faculty of MSU. Fundamentals of chemistry of biologically active substances: Training manual for students of colleges and universities.. The book is the compendium of the lecture course in chemistry of biologically active substances. It consists of four parts: medicines, drugs, pesticides and warfare agents. The information is delivered in form of lectures (17 lectures in total), every lecture course has a short introduction to the topic with historical background. To ensure the thrill and better understanding the author has adapted both pure scientifical articles and extracts from popular science articles about novel research in this interesting branch of chemistry. The book is thought to be used by students and teachers in chemical, pharmaceutical, medical and biological colleges and universities. The author hopes that this learning aid will help broaden students’ outlook and improve academically in the chemistry of biologically active substances. 3 TABLE OF CONTENT TABLE OF CONTENT....................................................................................................................................3 FOREWORD....................................................................................................................................................6 MEDICINES.....................................................................................................................................................9 LECTURE I. HISTORICAL OVERVIEW OF MEDICAL AND PHARMACEUTICAL PROFESSIONS..9 LECTURE II. DEVELOPMENT OF ORGANIC CHEMISTRY OF MEDICAL COMPOUNDS................9 1. Basic requirements for medicines............................................................................................17 2. Preclinical development of new chemical entities (NCEs)........................................................17 LECTURE III. DRUG DESIGN.....................................................................................................................19 LECTURE IV. CORRELATIONS BETWEEN STRUCTURE AND BIOLOGICAL ACTIVITY..............19 1. Effects of alkyl groups.............................................................................................................19 2. Effects of hydroxyl groups.......................................................................................................19 3. Effects of halogens in organic compounds...............................................................................20 4. Effects of nitro- and nitroso groups.........................................................................................20 5. Effects of nitrogen-containing groups......................................................................................21 6. Effects of acid groups.............................................................................................................21 7. Effect of saturation.................................................................................................................21 8. Dependence of biological effects upon some physical and chemical properties.........................21 9. Main directions for drug discovery and drug design................................................................23 10. Principles of automatic (computer-assisted) screening..........................................................23 11. Reproduction of known physiologically active substances......................................................24 12. Modification of known structures..........................................................................................24 13. Introduction of pharmacophore.............................................................................................24 14. Molecular modelling.............................................................................................................25 15. Composite medicines............................................................................................................25 16. Methodology of combinatorial chemistry...............................................................................25 17. Search of antimetabolites (antagonists of natural metabolites) based upon metabolism investigation..........................................................................................................................25 18. Scheme of new drug development..........................................................................................26 19. Correlations between structure and biological activity..........................................................27 LECTURE V. CLASSIFICATION OF DRUGS. MAIN HUMAN DISEASES AND BASIC CLASSES OF HUMAN DRUGS...............................................................................................................................29 1. Main human diseases and basic classes of human drugs..........................................................30 LECTURE VI. SYNTHESIS OF CHEMICAL COMPOUNDS OF ALIPHATIC SERIES.........................33 1. Halogen-containing derivatives of acyclic hydrocarbons.........................................................33 2. Alcohols and their derivatives.................................................................................................34 3. Aldehydes and acids. Vitamins F and В15................................................................................35 4. Amino acids............................................................................................................................37 LECTURE VII. MEDICAL COMPOUNDS OF ACYCLIC AND AROMATIC SERIES...........................40 1. Substituted cyclohexanes.........................................................................................................40 2. Synthesis of aromatic derivatives............................................................................................42 LECTURE VIII. CHEMISTRY OF MEDICINES CONTAINING VARIOUS HETEROCYCLES...........47 1. Synthesis of anti-neoplastic remedies from ethyleneimine (aziridine) and ethylene oxide (oxirane) group. History of anti-neoplastic remedies..............................................................47 2. Antibiotics, containing tetratomic azetidine ring......................................................................49 3. Remedies basing on 5-membered heterocycles.........................................................................52 4. Antibacterial nitrofurans.........................................................................................................53 5. Other furan derivatives...........................................................................................................54 6. Derivatives of 6-membered rings.............................................................................................55 4 7. Quinoline derivatives..............................................................................................................56 8. Pyrimidine derivatives with antiviral (anti-HIV) activity..........................................................57 9. Conclusion.............................................................................................................................58 NARCOTIC SUBSTANCES...........................................................................................................................59 LECTURE IX. AND X. NARCOTICS AND ADDICTION. HISTORICAL REVIEW................................59 1. Historical review....................................................................................................................59 2. Addiction, what is it?..............................................................................................................60 3. What are narcotics and what they look like..............................................................................60 4. Classification of narcotic and psychotropic agents..................................................................61 5. Cannabis................................................................................................................................63 6. Opiate drugs...........................................................................................................................63 7. Hypnotics and sedatives..........................................................................................................65 8. Psychostimulants....................................................................................................................66 9. Hallucinogens........................................................................................................................67 10. Volatile substances (volatile addictions)................................................................................69 LECTURE XI. PHYSIOLOGICAL EFFECTS OF DRUGS.........................................................................69 1. Cannabis................................................................................................................................71
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