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Medicinal Chemistry > Lecture 1 - Intro > Flashcards

Lecture 1 - Intro Flashcards

1
Q

How can you improve a drug?

A

By utilizing knowledge of or determining structure activity relationships (SAR)

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2
Q

Medicinal chemists study _____

A

SAR, structure activity relationships

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3
Q

What is qualitative SAR?

A

The relationship between the structure and the pharmacological effect

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4
Q

What are sigma bonds?

A

Single bonds formed by overlap of hybrid orbitals

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5
Q

Do sigma bonds usually have complete freedom of rotation?

A

Yes

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6
Q

What do P orbitals form?

A

Pi bonds

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7
Q

Do pi bonds have complete freedom of rotation?

A

No

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8
Q

What is electronegativity?

A

The ability to attract electron density

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9
Q

What are the most important electronegative atoms in med chem?

A
  • Halogens (F, Br, I, & Cl)
  • Nitrogen
  • Oxygen
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10
Q

What are the 2 ways that electron density can move through a molecule?

A

1) Resonance - movement of electron density through pi bonds (through a conjugated system)
2) Induction - movement of electron density through sigma bonds (through saturated carbons)

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11
Q

What determines if a functional group is ED or EW?

A
  • If the donating or withdrawing happens through resonance or induction
  • Also, the electronegativity, presence of lone pairs of electrons, multiple bonds, and the molecular geometry
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12
Q

Which functional groups are ED when resonance and EW when induction?

A

-OH, -OR, -NH2, and -NR2

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13
Q

Which functional groups are always EW, whether resonance or induction?

A

-COOH, -COOR, -COR, -CHO, -SOR, -SO2R, -SO2RNR2, -NO2, and -CN

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14
Q

Which functional groups are ED when induction?

A

-O-, -S-, -COO-, and -CH3

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15
Q

Which functional groups are EW when induction?

A

-NH3+, -NR3+, -F, -Cl, -Br, and -I

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16
Q

Will a molecule be EW or ED when it is attached to a carbon or sulfur that is double bonded to an oxygen?

A

Strongly EW

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17
Q

What are the rules for pH and pKa if you want to ionize free acid (HA) to conjugate base (A-)?

A

pH > pKa

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18
Q

What are the rules for pH and pKa if you want to minimize the ionization of HA to A-?

A

pH < pKa

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19
Q

What are the rules for pH and pKa if you want to ionize free base (B) to conjugate acid (HB+)?

A

pH < pKa

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20
Q

What are the rules for pH and pKa if you want to minimize the ionization of B to HB+?

A

pH > pKa

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21
Q

What happens to ionization when pH = pKa?

A

You get 50% ionization

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22
Q

It is always assumed that the solvent is _____

A

Water

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23
Q

How can you explain why the proton of COOH is acidic?

A

Its inductive effects in the neutral form and the resonance effects in the ionized form

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24
Q

Why are drugs usually marked in a salt form?

A

Because they are easier to make into solid dosage forms and they dissolve more readily in water

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25
What is an example of a strong acid?
HCl
26
What are 2 examples of weak acids?
Maleic & succinic acid
27
What are 2 examples of strong bases?
NaOH and KOH
28
What is an example of a weak base?
NaH2PO4 (monosodium phosphate)
29
When you see "HCl" on a label does that mean there is acid in the drug formulation?
NO, it means HCl was mixed with the original drug to form a salt; there is no free HCl in the compound
30
What does hydroscopic mean?
Absorbs atmospheric water
31
What is a substituent?
An atom or group of atoms substituted in place of an H atom on the parent organic compound
32
What are you supposed to do when asked to make a substitution on the exam?
Replace a hydrogen atom on the parent molecule with a functional group
33
Alkanes have a ____ carbon center
Tetrahedral
34
Alkanes are ____ hybridized
sp3
35
Are alkanes polar? Hydrophobic or hydrophilic?
Nonpolar and hydrophobic
36
Are alkanes ED or EW?
Always ED
37
Alkenes are ____ hybridized
sp2
38
Are alkenes polar? Hydrophobic or hydrophilic?
Nonpolar and hydrophobic
39
What is the geometry of alkenes?
Planar
40
Are alkenes EW or ED?
Can be either depending on substituents
41
Alkynes are ____ hybridized
sp
42
Are alkynes polar? Hydrophobic or hydrophilic?
Nonpolar and hydrophobic
43
Are alkynes EW or ED?
Mostly EW
44
Alkanes and alkenes can only form _____ interactions
Van der Waals
45
Can alkanes and alkenes form bonds with water?
No, so they are not water soluble
46
What does a larger and more branched alkyl chain mean for hydrophilicity and lipophilicity?
Less hydrophilic and more lipophilic
47
Halogenated hydrocarbons are generally ___ hydrophilic than the alkyl form
Less
48
Which halogen is the most electronegative and which is the least?
- Most = F | - Least = I
49
Which halogen is the smallest and which is the largest?
- Smallest = F | - Largest = I
50
Are halogenated hydrocarbons hydrophobic or hydrophilic?
Hydrophobic
51
Are halogens of saturated hydrocarbons EW or ED by induction?
EW
52
When is OH ED?
Through resonance
53
When is OH EW?
Through induction
54
Are alcohols H-bond donors or acceptors?
Both
55
What happens to alcohol solubility when the length of a hydrocarbon increases?
Solubility decreases, but it depends on the position of the OH
56
Are phenols or aliphatic alcohols more acidic?
Phenols
57
Are alcohols acidic?
Not really
58
What is the typical pKa of phenols?
9-10, but depends on other substituents
59
Are aromatic hydrocarbons hydrophobic or hydrophilic when they are unsubstituted?
Hydrophobic
60
Is a sulfhydryl group (-SH) polar?
Yes, but only weakly polar
61
Is SH ED or EW?
Always ED
62
Is R-SH or R-OH more acidic?
R-SH because it is more willing to give up it's proton
63
Are ethers polar?
Yes, weakly
64
Are thioethers polar?
Yes, weakly
65
Is alkoxy (-OR) EW or ED?
Both
66
Is thioalkoxy (-SR) EW or ED?
ED
67
Is sulfoxide ED or EW?
Always EW because it is a sulfur w/ a double bonded oxygen
68
Does sulfoxide have a lone pair of electrons?
Yes
69
Is sulfoxide polar?
Yes, highly
70
Is sulfone ED or EW?
Always strongly EW
71
Is sulfone polar?
Highly polar
72
Acetone is ___ hybridized
sp2
73
Is a carbonyl (C=O) polar?
Yes
74
Are aldehydes and ketones EW or ED?
Always EW
75
What are aldehydes and ketones in rapid equilibrium with and what does this form?
- In equilibrium with alcohol | - Forms hemiacetal and hemiketal
76
Are amines polar?
Yes
77
What types of interactions can amines form?
- H-bonds - Dipole-dipole - Ion-dipole
78
Is the neutral form of amine EW or ED?
- ED through resonance | - EW through induction
79
Is the nitrogen of amine acidic or basic?
Basic, so it can accept a proton
80
What types of interactions can carboxylic acids form?
- H-bonds - Dipole-dipole - Ion-dipole
81
Are carboxylic acids polar?
Yes
82
Are carboxylic acids EW or ED?
- EW when in neutral form | - ED when in anion form
83
Should a carboxylic acid be used when doing a substitution in a molecule that is EW?
No, because at physiological pH it readily deprotonates, making it ED
84
Are esters polar?
Yes
85
What types of interactions can esters form?
Only H-bonds with water
86
Are esters EW or ED?
Always EW
87
What is important to note about RCOOR' (ester)?
- Susceptible to hydrolysis - Catalyzed by esterases - Frequently used a prodrug to facilitate the absorption of carboxylic acid drugs
88
Are amides polar?
Yes
89
What types of interactions can amides form?
- H-bonds with water | - Dipole-dipole
90
Are amides EW or ED?
Always EW
91
Is the N of RCONR2 (amide) basic?
No because the lone pair of electrons forms a resonance structure and is not available to accept a proton
92
Are amides acidic or basic at physiological pH?
Neutral
93
Nitriles and carbonates have properties similar to _____
Esters
94
Carbamates have properties between ____ and _____
Esters and amides
95
Ureas have properties similar to _____ and are ___ stable
- Amides | - Very
96
Are aminidines and guanidines polar?
Highly polar
97
What types of interactions can aminidines and guanidines form?
- H-bonds - Dipole-dipole - Ion-dipole with water
98
Are aminidines and guanidines EW or ED in the neutral form?
- Aminidines are EW | - Guanidines are weakly ED and weakly EW due to the electronegativity of nitrogen
99
Are aminidines and guanidines EW or ED in the ionized form?
- Aminidines are EW whether negative or positive | - Guanidines are EW whether negative or positive
100
Are aminidines and guanidines more or less basic than amines?
More
101
What should you use if you want to add something to a molecule that is EW?
Nitro
102
Is a nitro polar?
Only slightly
103
Are nitros EW or ED?
Highly EW
104
Can the negative O on a nitro accept an H+?
No
105
Sulfonic acids have properties similar to ______
Carboxylic acids
106
Are sulfonic acids EW or ED?
EW
107
Are sulfonic acids or carboxylic acids more polar?
Sulfonic acids
108
Sulfonamides have properties similar to _____
Amides
109
Are sulfonamides EW or ED?
EW
110
Are sulfonamides or amides more acidic?
Sulfonamides
111
Which molecules are commonly involved in heterocycles?
N, O, or S
112
What are the requirements for a compound to be aromatic?
- Cyclic - Planar - Delocalized conjugated - # of electrons in p orbitals capable of forming pi bonds satistfies 4n + 2
113
What is needed for a compound to be considered delocalized conjugated?
- Every atom in ring has p orbital that can form pi bonds | - Every atom is sp2 hybridized
114
Are the interactions between aromatic rings considered dipole-dipoles interactions?
No, because an aromatic ring has more than 2 poles
115
What are the 3 types of aromatic/pi stacking interactions?
- T-shaped or edge to face - Parallel displaced - Sandwich

Medicinal Chemistry (14 decks)

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