Intro_Org_2009_2 - Organic Chemistry and Drug Discovery...

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Organic Chemistry and Drug Discovery Professor Michael J. Krische The properties of organic molecules depend upon their structures Digitoxin - A Drug Based on Digitalis Extract Used to Treat Congestive Heart Failure and Atrial Fibrillation H 3 C OH H 3 C O O H 3 C OH O H H O O O H 3 C OH O O H 3 C OH HO H H Purple Foxglove, i.e. Digitalis Purpurea Glycone - Modulates Drug Delivery and Metabolism Steroidal Aglycon - The "War-Head" of Digitoxin Plant Extraction A Broad Scientific Question : What is the nature of matter? Organic Chemistry : The study of carbon containing compounds. Since virtually all naturally occurring compounds contain carbon, organic chemistry is inextricably tied to living systems.
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Subtle Differences in Structure Confer Differences in Properties Some Familiar Naturally Occurring Substances or “Natural Products” Organic Chemistry and Drug Discovery Professor Michael J. Krische
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Naturally Occurring Fragrant Esters Organic Chemistry and Drug Discovery Professor Michael J. Krische Subtle Differences in Structure Confer Differences in Properties CH 3 Rasberry Aroma O O CH 3 Pear Aroma Apple Aroma O O CH 3 H 3 C O CH 3 H 3 C O Pineapple Aroma O CH 3 O H 3 C CH 3 Rum Aroma O O Banana Aroma Orange Aroma O O CH 3 H 3 C H 3 CO ( C H 2 ) 7 CH 3 O Peach Aroma O H 3 C H 3 C CH 3 CH 3 O Honey Aroma O O H 3 C
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CC (+)-Carvone (Caraway) (-)-Carvone (Spearmint) M i r r o r P l a n e OO H H Left Hand Right Hand M i r r o r P l a n e Organic Molecules Can Have “Handedness” - They Can Be “Chiral”. Pair of Chiral Molecular are Referred to as Enantiomers. Tetrahedral Carbon Centers Possessing Four Different Groups Can Exist as Non- Superimposable Mirror Images – They are Enantiomers. Organic Chemistry and Drug Discovery Professor Michael J. Krische
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N C N O O O O H N C N O O O O H (+)-Thalidomide (Sedative, anti-Nausea) (-)-Thalidomide ( Severe Birth Defects ) H H M i r r o r P l a n e OH HS Antidote for Hg Poisening Optical Atrophy ( Blindness ) M i r r o r P l a n e O HO O SH H 3 C H 3 C NH 2 H H 2 NH CH 3 CH 3 Different Enantiomers Can Have Wildly Different Biological Profiles O O OH O O O O CH 3 OH O O OH H O O O H 3 C If a molecule has n -chiral centers, there are 2 n possible combinations possible, termed “stereoisomers.” The FDA now requires that chiral molecules be prepared as single entities. Over 50% of the world’s top-selling drugs are single enantiomers and it is estimated that 80% of all drugs currently entering development are chiral and will be marketed as single-enantiomer entities . Taxol - Bark of Pacific Yew Tree Potent Anti-Cancer Agent 11 Stereocenters 2048 Possible Isomers! Organic Chemistry and Drug Discovery Professor Michael J. Krische
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Where Do Drugs Come From ? 61% of the 877 small molecules introduced as drugs worldwide from 1981- 2002 were inspired by “Natural Products” ( J. Nat. Prod. 2003, 1022). Hence, the discovery, biological profiling (SAR), and preparation of natural products is of paramount importance in terms of public health.
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Intro_Org_2009_2 - Organic Chemistry and Drug Discovery...

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