The Organic Chemistry of Drug Synthesis, Volume 7

The classic reference on the synthesis of medicinal agents -- now completely updated The seventh volume in the definitive series that provides a quick yet thorough overview of the synthetic routes used to access specific classesof therapeutic agents, this volume covers approximately 220 new non-proprietary drug entities introduced since the publication of Volume 6. Many of these compounds represent novel structural types firstidentified by sophisticated new cell-based assays. Specifically, a significant number of new antineoplastic and antiviral agents are covered. As in the previous volumes, materials are organized by chemical class and syntheses originate with available starting materials. Organized to make the information accessible, this resource covers disease state, rationale for method of drug therapy, and the biological activities of each compound and preparation. The Organic Chemistry of Drug Synthesis, Volume 7 is a hands-on reference for medicinal and organic chemists, and a great resource for graduate and advanced undergraduate students in organic and medicinal chemistry. 9780470180662.pdf THE ORGANIC CHEMISTRY OF DRUG SYNTHESIS 4 CONTENTS 10 Preface 14 1 OPEN-CHAIN COMPOUNDS 18 1. Peptidomimetic Compounds 19 A. Antiviral Protease Inhibitors 19 1. Human Immunodeficiency Virus 19 2. Human Rhinovirus 26 2. Miscellaneous Peptidomimetic Compounds 28 References 36 2 ALICYCLIC COMPOUNDS 38 1. Monocyclic Compounds 38 A. Prostaglandins 38 B. Antiviral Agents 42 C. Miscellaneous Monocyclic Compounds 46 2. Polycyclic Compounds: Steroids 48 A. 19-Nor Steroids 48 B. Corticosteroid Related Compounds 51 3. Polycyclic Compounds 55 References 57 3 MONOCYCLIC AROMATIC COMPOUNDS 60 1. Arylcarbonyl Derivatives 60 2. Biphenyls 64 3. Compounds Related to Aniline 67 4. Compounds Related to Arylsulfonic Acids 70 5. Diarylmethanes 75 6. Miscellaneous Monocyclic Aromatic Compounds 77 References 84 4 CARBOCYCLIC COMPOUNDS FUSED TO A BENZENE RING 86 1. Indenes 86 2. Naphthalenes 90 3. Tetrahydronaphthalenes 91 4. Other benzofused carbocyclic compounds 96 References 98 5 FIVE-MEMBERED HETEROCYCLES 100 1. Compounds with One Heteroatom 100 2. Compounds with Two Heteroatoms 108 A. Oxazole and Isoxazoles 108 B. Imidazoles and a Pyrrazole 111 C. Thiazoles 116 D. Triazoles 120 E. Tetrazoles 126 References 129 6 SIX-MEMBERED HETEROCYCLES 132 1. Compounds with One Heteroatom 132 A. Pyridines 132 B. Reduced Pyridines 134 C. Miscellaneous 136 2. Compounds with Two Heteroatoms 138 A. Pyrimidines 138 B. Miscellaneous Six-Membered Heterocycles 150 References 153 7 FIVE-MEMBERED HETEROCYCLES FUSED TO ONE BENZENE RING 156 1. Compounds with One Heteroatom 156 A. Benzofurans 156 B. Indoles 158 C. Indolones 165 D. Miscellaneous Compounds with One Heteroatom 170 2. Five-Membered Rings with Two Heterocyclic Atoms 173 A. Benzimidazoles 173 B. Miscellaneous Compounds 175 References 177 8 SIX-MEMBERED HETEROCYCLES FUSED TO ONE BENZENE RING 180 1. Compounds with One Heteroatom 180 A. Benzopyrans 180 B. Quinolines and Their Derivatives 184 C. Quinolone Antibacterial Agents 189 2. Compounds with Two Heteroatoms 193 A. Benzoxazines 193 B. Quinazolines 195 C. Miscellaneous Benzo-Fused Heterocycles 201 References 203 9 BICYCLIC FUSED HETEROCYCLES 206 1. Compounds with Five-Membered Rings Fused to Six-Membered Rings 206 A. Compounds with Two Heteroatoms 206 B. Compounds with Three Heteroatoms 208 C. Compounds with Four Heteroatoms 212 2. Compounds with Two Fused Six-Membered Rings 225 3. Miscellaneous Compounds with Two Fused Heterocyclic Rings: Beta Lactams 230 References 232 10 POLYCYCLIC FUSED HETEROCYCLES 234 1. Compounds with Three Fused Rings 234 2. Compounds with Four Fused Rings 245 3. Compounds with Five or More Fused Rings: Camptothecins 247 References 249 Subject Index 250 Cross Index of Biological Activity 258 Cumulative Index 262 THE ORGANIC CHEMISTRY OF DRUG SYNTHESIS......Page 4 CONTENTS......Page 10 Preface......Page 14 1 OPEN-CHAIN COMPOUNDS......Page 18 1. Human Immunodeficiency Virus......Page 19 2. Human Rhinovirus......Page 26 2. Miscellaneous Peptidomimetic Compounds......Page 28 References......Page 36 A. Prostaglandins......Page 38 B. Antiviral Agents......Page 42 C. Miscellaneous Monocyclic Compounds......Page 46 A. 19-Nor Steroids......Page 48 B. Corticosteroid Related Compounds......Page 51 3. Polycyclic Compounds......Page 55 References......Page 57 1. Arylcarbonyl Derivatives......Page 60 2. Biphenyls......Page 64 3. Compounds Related to Aniline......Page 67 4. Compounds Related to Arylsulfonic Acids......Page 70 5. Diarylmethanes......Page 75 6. Miscellaneous Monocyclic Aromatic Compounds......Page 77 References......Page 84 1. Indenes......Page 86 2. Naphthalenes......Page 90 3. Tetrahydronaphthalenes......Page 91 4. Other benzofused carbocyclic compounds......Page 96 References......Page 98 1. Compounds with One Heteroatom......Page 100 A. Oxazole and Isoxazoles......Page 108 B. Imidazoles and a Pyrrazole......Page 111 C. Thiazoles......Page 116 D. Triazoles......Page 120 E. Tetrazoles......Page 126 References......Page 129 A. Pyridines......Page 132 B. Reduced Pyridines......Page 134 C. Miscellaneous......Page 136 A. Pyrimidines......Page 138 B. Miscellaneous Six-Membered Heterocycles......Page 150 References......Page 153 A. Benzofurans......Page 156 B. Indoles......Page 158 C. Indolones......Page 165 D. Miscellaneous Compounds with One Heteroatom......Page 170 A. Benzimidazoles......Page 173 B. Miscellaneous Compounds......Page 175 References......Page 177 A. Benzopyrans......Page 180 B. Quinolines and Their Derivatives......Page 184 C. Quinolone Antibacterial Agents......Page 189 A. Benzoxazines......Page 193 B. Quinazolines......Page 195 C. Miscellaneous Benzo-Fused Heterocycles......Page 201 References......Page 203 A. Compounds with Two Heteroatoms......Page 206 B. Compounds with Three Heteroatoms......Page 208 C. Compounds with Four Heteroatoms......Page 212 2. Compounds with Two Fused Six-Membered Rings......Page 225 3. Miscellaneous Compounds with Two Fused Heterocyclic Rings: Beta Lactams......Page 230 References......Page 232 1. Compounds with Three Fused Rings......Page 234 2. Compounds with Four Fused Rings......Page 245 3. Compounds with Five or More Fused Rings: Camptothecins......Page 247 References......Page 249 Subject Index......Page 250 Cross Index of Biological Activity......Page 258 Cumulative Index......Page 262

the Classic Reference On The Synthesis Of Medicinal Agents —now Completely Updated

the Seventh Volume In The Definitive Series That Provides A Quick Yet Thorough Overview Of The Synthetic Routes Used To Access Specific Classesof Therapeutic Agents, This Volume Covers Approximately 220 New Non-proprietary Drug Entities Introduced Since The Publication Of Volume 6.many Of These Compounds Represent Novel Structural Types Firstidentified By Sophisticated New Cell-based Assays. Specifically, A Significant Number Of New Antineoplastic And Antiviral Agents Are Covered.

as In The Previous Volumes, Materials Are Organized By Chemical Class And Syntheses Originate With Available Starting Materials. Organized To Make The Information Accessible, This Resource Covers Disease State, Rationale For Method Of Drug Therapy, And The Biological Activities Of Each Compound And Preparation. The Organic Chemistry Of Drug Synthesis, Volume 7 Is A Hands-on Reference For Medicinal And Organic Chemists, And A Great Resource For Graduate And Advanced Undergraduate Students In Organic And Medicinal Chemistry.

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the Series Meets The Needs Of Practitioners In The Field Who Seek A Quick Overview Of The Synthetic Routes That Have Been Used To Access Specific Classes Of Therapeutic Agents. Volume 5 Covers The Literature On The Synthesis Of Medicinal Agents From 1988 To 1993. The Materials Are Arranged And Discussed In Terms Of Chemical Structure; Thus, The Preparation And Detailed Organic Chemistry Of The Classes Are Presented In A Unified Way. Only Drugs Which Have Been Granted A Us Adopted Name Are Included. For Synthetic Organic, Pharmaceutical, Medicinal, And Heterocyclic Chemists. Annotation C. Book News, Inc., Portland, Or (booknews.com)

Annotation. The classic reference on the synthesis of medicinal agents --now completely updated The seventh volume in the definitive series that provides a quick yet thorough overview of the synthetic routes used to access specific classesof therapeutic agents, this volume covers approximately 220 new non-proprietary drug entities introduced since the publication of Volume 6. Many of these compounds represent novel structural types firstidentified by sophisticated new cell-based assays. Specifically, a significant number of new antineoplastic and antiviral agents are covered. As in the previous volumes, materials are organized by chemical class and syntheses originate with available starting materials. Organized to make the information accessible, this resource covers disease state, rationale for method of drug therapy, and the biological activities of each compound and preparation. The Organic Chemistry of Drug Synthesis, Volume 7 is a hands-on reference for medicinal and organic chemists, and a great resource for graduate and advanced undergraduate students in organic and medicinal chemistry Focuses on the synthetic aspects of the pharmaceutical industry. This book discusses the synthetic routes and strategies devised to prepare a pharmaceutically active agent, utilizing common drugs as examples