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Functional groups


What are functional groups? Specific groups within a molecule possessing very characteristics properties and determines the reactivity of molecules
Amphoetric a molecule possessing multiple functional groups therefore possessing both acid and base properties
What determines physiochemical properties and subsequent drug binding interaction? also by that influencing pharmacokinetic properties functional groups
What are isomers? Same chemical formula different structures. May not always share similar properties
Stereochemistry study if static and dynamic aspects of 3D shapes of molecules understanding structure and reactivity
Chiral an object that cannot be superimposed on its mirror image .. and it's an central concept in stereochemistry
Enantiomers 2 mirror image of chiral molecules
T/F: enantiomers of a chiral drug have identical physiochemical properties in an achiral environment True .. However, in a chiral nvironment 1 enantiomer may display different chemical and pharmacologic behavior .. like living systems are chiral
Why is chirality important? because of receptor binding considerations
What is the Easson-Stedman's hypothesis The more potent enentiomer must make a minimum of 3 intermolecular interactions with the surface of the biological target must be made for the enantiomer to be more potent
What is optical activity? The ability of compounds to rotate the plane of polorized light - typically converted into specific rotation
Enantiomers have _____ and opposite rotations Equal .... divides into 2: * (+) Dextrorotatory and (-) Levorotatory
What is optical purity? measure of the excess of one enantiomer
How are single enantiomers produced? ** Resolution: separate isomer out of a racemic mixture - wasteful (50% of product is useless) ** chiral synthesis" Stereoselective design into the synthetic route
Priority rules in describing configurations 1. Higher atomic # 2. Higher atomic mass 3. if 2 have same priority, consider 2nd degree groups 4. considerations for cyclic compounds are the same
Can a chiral drug have more than 1 chiral center? yes, and when assigning configuration you have to assign for each center
Diastereomers stereoisomers that are non enantiomers .. seen in compounds with more than one chiral center .. have different physical and chemical properties
Stereospecific reaction one stereoisomers of the reactant gives one stereoisomer of the product, while a different reactant gives a different product
stereoselective reaction reaction in which a single reactant give 2 or more stereoisomeric products, and one or more is preferred over the other.
T/F: All stereospecific reactions are stereoselective and all stereoselective are stereospecific FALSE. First oart of the question is true .. second part Stereoselectives can't be stereospecific.
Structure activity relationships the study of the relationships between a drug's molecular structure and its biological activity. SAR studies are critical to designing a pharmaceutical compound w/ great potency and least side effects
Qualitive SARs define relationships between structure and behavior based on comparing properties of or more analogs (structurally similar compounds) with the compound of interest.
SAR in practice - change size and shape of lead compounds by vary # of methylene groups in chains and rings ... Increase or decrease degree of unsaturation .... introduce or remove ring system
Changing the # of methylene groups can _______ lipophilicity and _______ water solubility Increase, decrease
What can introducing each one of those substituents do: Methyl groups, Halogens, Hydroxyl groups, basic groups, acidic groups Methyl groups: increase rate of metabolism .. Halogens: Mostly F (CF3) & Cl .. Hydroxyl group: increases hydrophilicity ... Basic groups: ^ H binding & acid base interactions .. Acidic groups:^ H bonding and aids salt formation & increase water solubility
The development of a (Q)SARs model requires 3 components: 1. data set provide activity for a group of chemicals 2. A structural criteria or structure related property data set for the same group of chemicals 3. A means of relating these 2 data arrays
SAR Models are defined and limited by The nature and quality of the data used to develop them and strictly applicable only to the data set used to generate them, and capable of predicting within reasonable boundaries outside the data set
Utility of QSAR studies identifies chemical structures w/ good inhibitory effects on specific targets .. predict portion coefficient .. also used to study interactions between the structural domains of proteins
Created by: amiqnais