Medicinal Chemistry - Pharm 201 Questions and Verified Answers, 100%
Guarantee
Not every molecule/compound is a: - drug
functional group - the portion of a molecule that is active in a chemical reaction and that
determines the properties of many organic compounds
amine - R-NH2 (primary), R-NH-R (Secondary), R-NR2, (tertiary)
alkane - R-CH3
alkene - R-CH=CH2 (double bond)
alkyne - R-C-CH (triple bond)
benzene ring (phenyl) - R-ring of carbons (with double bonds)
phenol - Benzene ring with -OH
tert-butyl - -C(CH3)3
Alcohol - R-OH (can be primary, secondary, tertiary)
ether - R-O-R
alkyl halide - R-X (halo group)
,thiol - R-SH
aldehyde - R-C=O-H
ketone - R-C=O-R
ester - R-C=O-O-R
carboxylic acid - R-C=O-O-H
amide - R-C=O-N-(H,R)
sulfonamide - O=S=O-N
Properties that functional groups affect (5): - 1. Lipid and water solubility
2. route of administration
3. ability to interact with specific targets
4. mechanism of action (inhibitor, effector, etc)
5. Metabolism and elimination (how long drug stays in body)
How are acids and bases affected by hydrophobic/hydrophilic functional groups? -
hydrophobic groups, which are non-polar, have electron donating effects, which makes it
harder for the molecule to donate a proton. This decreases its acidity.
Hydrophilic groups, which are polar, tend to have electron withdrawing effects, enhancing
acidity by stabilizing the negative charge on the conjugate base.
Functional groups can be altered to enhance: (4) - - activity
, - absorption
- decrease side effects
- other therapeutic benefits
What are the three chemical properties of functional groups? - 1. electronic effect
2. solubility effect
3. steric effect
two types of electronic effects: - - inductive
- resonance
Inductive effects - Caused by the electronegativity of an atom in comparison to the
surrounding atoms in the molecule.
The electronegative atom transmits the electron density onto itself from surrounding atoms.
Resonance effect - When lone pairs of electrons are constantly moving, being equally
shared (between adjacent sp2 (double bonded) atoms).
sp, sp2, sp3 - sp: 2 lone pairs (if not double/triple bonded)
sp3: no lone pairs (if not double/triple bonded)
ortho vs para - ortho: next to each other on a benzene ring.
para: across from each other on a benzene ring.
Order of electronegativity in atoms - F -> O -> Cl -> N -> Br -> I -> S -> C -> H -> P
dipole - Molecule with both positive and negative regions
Guarantee
Not every molecule/compound is a: - drug
functional group - the portion of a molecule that is active in a chemical reaction and that
determines the properties of many organic compounds
amine - R-NH2 (primary), R-NH-R (Secondary), R-NR2, (tertiary)
alkane - R-CH3
alkene - R-CH=CH2 (double bond)
alkyne - R-C-CH (triple bond)
benzene ring (phenyl) - R-ring of carbons (with double bonds)
phenol - Benzene ring with -OH
tert-butyl - -C(CH3)3
Alcohol - R-OH (can be primary, secondary, tertiary)
ether - R-O-R
alkyl halide - R-X (halo group)
,thiol - R-SH
aldehyde - R-C=O-H
ketone - R-C=O-R
ester - R-C=O-O-R
carboxylic acid - R-C=O-O-H
amide - R-C=O-N-(H,R)
sulfonamide - O=S=O-N
Properties that functional groups affect (5): - 1. Lipid and water solubility
2. route of administration
3. ability to interact with specific targets
4. mechanism of action (inhibitor, effector, etc)
5. Metabolism and elimination (how long drug stays in body)
How are acids and bases affected by hydrophobic/hydrophilic functional groups? -
hydrophobic groups, which are non-polar, have electron donating effects, which makes it
harder for the molecule to donate a proton. This decreases its acidity.
Hydrophilic groups, which are polar, tend to have electron withdrawing effects, enhancing
acidity by stabilizing the negative charge on the conjugate base.
Functional groups can be altered to enhance: (4) - - activity
, - absorption
- decrease side effects
- other therapeutic benefits
What are the three chemical properties of functional groups? - 1. electronic effect
2. solubility effect
3. steric effect
two types of electronic effects: - - inductive
- resonance
Inductive effects - Caused by the electronegativity of an atom in comparison to the
surrounding atoms in the molecule.
The electronegative atom transmits the electron density onto itself from surrounding atoms.
Resonance effect - When lone pairs of electrons are constantly moving, being equally
shared (between adjacent sp2 (double bonded) atoms).
sp, sp2, sp3 - sp: 2 lone pairs (if not double/triple bonded)
sp3: no lone pairs (if not double/triple bonded)
ortho vs para - ortho: next to each other on a benzene ring.
para: across from each other on a benzene ring.
Order of electronegativity in atoms - F -> O -> Cl -> N -> Br -> I -> S -> C -> H -> P
dipole - Molecule with both positive and negative regions
