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84 Cards in this Set
- Front
- Back
- 3rd side (hint)
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Medicinal Chemistry |
Influence of chemical structure on biological acitvity |
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Desolvation |
Removal of water molecules from polar regions of drug |
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Removal of water molecules from polar regions of a molecule |
desolvation |
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6 Noncovalent interactions (strongest to weakest) |
Ionic H-bond Van der Waals Dipole-dipole Ion-dipole Induced dipole |
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interaction between quaternary ammonium ion and aromatic ring |
induced dipole |
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example of induced dipole interaction |
interaction between quaternary ammonium ion and aromatic ring |
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Alkanes are stable under what 5 conditions? |
ambient aqueous acidic basic heat |
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How are alkanes usually excreted? |
unchanged |
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Which location does CYP450 react with which type of aliphatic molecules?? |
Terminal or adjacent Carbon of Hydrocarbon chain |
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alkenes have what that results in what? |
double bond geometric isomers |
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which type(s) of noncovalent interactions do alkanes experience? |
Van der Waals |
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Which type(s) of noncovalent interactions do alkenes experience? |
weak dipole |
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What reactions are alkenes vulnerable to? |
oxidation peroxidation epoxidation reduction hydration |
5 |
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glutathione n-acetyl cysteine |
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n-acetyl cysteine |
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glutathione |
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Which is lower energy? axial-trans equatorial-trans |
equatorial trans |
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What isomer variants are generated by polysubstitution? |
cis and trans |
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How many carbons does a ring need for conformational isomers? |
6+ |
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What are the variations of conformational isomerism? |
boat and chair |
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Axial vs equatorial is a product of |
polysubstitution and conformational isomerisms |
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how are cycloalkanes similar to alkenes? |
both can have geometric isomers |
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aromatic hydrocarbons are vulnerable to which type of metabolic rxn? |
aromatic hydroxylation |
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description of the mechanism of aromatic hydroxylation |
electrophilic |
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Aromatic hydroxylation may involve which reaction mechanism as an intermediary? |
epoxidation |
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epoxidation may be an intermediate mechanism for this type of reaction |
aromatic hydroxylation |
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aromatic hydroxylation via epoxidation |
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aromatic hydroxylation |
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describe the geometric conformation of aromatic hydrocarbons |
flat |
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aromatic hydrocarbons experience which noncovalent interaction(s)? |
Van der Waals induced dipole |
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Noncovalent interaction(s) experienced by halogenated hydrocarbons: |
van=der waals |
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what "strengths" do halogenated hydrocarbons have over regular hydrocarbons? what "advantage" does this result in? |
Higher chemical stability not readily excreted by kidney Longer half life |
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These funx groups are Permanent dipoles |
alcohols |
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How can alcohols be structured to be more water-soluble? |
hydroxyl near center of molecule |
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alcohols with hydroxyls far from th molecular center are.... |
less water soluble |
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This type of funx group forms strong H-bonds because..... |
Alcohols permanent dipoles |
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Which alcohol(s) are stable against oxidases? |
tertiary |
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Tertiary alcohols are stable against what? |
oxidases |
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Which funx group(s) is/are mildly acidic? |
phenols |
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pKa of Phenol |
9.96 |
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What metabolic rxn is most common for phenols? |
G and S conjugation |
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CYPs perform which rxn(s) on Phenols? |
oxidation hydroxylation |
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Methylation is a metabolic rxn that can happen to which funx group(s)? |
phenols |
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Phenols can experience which metabolic rxn(s)? |
oxidation/hydroxylation methylation G and S conjugation |
3 types |
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Ether general structure |
ROR |
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ROR is what? |
Ether |
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Ethers experience which noncovalent interaction(s)? |
weak H-bonding |
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Solubility of these functional groups can be described as weak in water: |
Ethers |
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The solubility of ethers can be described as: |
poor in water |
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Noncovalent Interaction(s) experienced by Aldehydes and Ketones: |
H-bond to water |
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Reduction of these functional group(s) produce alcohols: |
ketones aldehydes |
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Enol is produced by resonance of a: |
ketone |
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A resonance of a ketone could be described as an: |
enol |
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form of acetone |
enol |
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Ethers are metabolized by which rxn(s)? |
none |
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These functional groups are generally excreted unchanged |
ethers alkanes |
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What physiochemical effects can occur from the addition of an amine? |
solubilization as a free base or salt of an amine binding site |
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Addition of this functional group(s) can solubilize a drug by which means? |
amine acts as free base or salt of amine |
1 2 |
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Amines experience which noncovalent interaction(s)? |
H-bonding steric effects |
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Substitution with which agents decrease the basicity of amines? |
oxidizing groups aromatic rings |
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What reacts to form quaternary ammonium salts? |
amines and acid |
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Amines can under go these metabolic rxn(s) |
dealkylation deamination conjugation |
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Monoamine oxidaze and diamine oxidase perform this metabolic rxn |
deamination |
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metabolic deamination is catalyzed by the following enzyme(s) |
MAO DAO |
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Carboxylic acids undergo the following metabolic reaction(s) |
G conjugation oxidation of beta C by coenzyme A |
2 applies to fatty acids |
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Fatty acids are described molecularly as |
carboxylic acid with aliphatic tail |
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carboxylic acid with aliphatic tail |
fatty acid |
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Fatty acids undergo which metabolic rxn by which cofactor? |
oxidation by coenzyme A |
on beta carbon |
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Functional derivative(s) of carboxylic acids |
esters amides |
2 |
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Esters and amides are functional derivatives of which type(s) of functional groups? |
Carboxylic acids |
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very strong acids like mineral acids |
sulfonic acids |
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sulfonic acids experience these type(s) of noncovalent interactions |
ion-dipole with water |
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Sulfonamides are in what state |
solid form |
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Solubility of sulfonamides can be described as: |
insoluble |
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Solubility of thioethers can be described as: |
lipophilic |
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These funx groups are produced from metabolism of thioethers |
sulfoxides/sulfones |
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Sulfoxides and sulfones are products of: |
Thioethers |
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esterases |
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