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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
Q

What is an example of a strong acid?

A

HCl

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26
Q

What are 2 examples of weak acids?

A

Maleic & succinic acid

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27
Q

What are 2 examples of strong bases?

A

NaOH and KOH

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28
Q

What is an example of a weak base?

A

NaH2PO4 (monosodium phosphate)

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29
Q

When you see “HCl” on a label does that mean there is acid in the drug formulation?

A

NO, it means HCl was mixed with the original drug to form a salt; there is no free HCl in the compound

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30
Q

What does hydroscopic mean?

A

Absorbs atmospheric water

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31
Q

What is a substituent?

A

An atom or group of atoms substituted in place of an H atom on the parent organic compound

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32
Q

What are you supposed to do when asked to make a substitution on the exam?

A

Replace a hydrogen atom on the parent molecule with a functional group

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33
Q

Alkanes have a ____ carbon center

A

Tetrahedral

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34
Q

Alkanes are ____ hybridized

A

sp3

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35
Q

Are alkanes polar? Hydrophobic or hydrophilic?

A

Nonpolar and hydrophobic

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36
Q

Are alkanes ED or EW?

A

Always ED

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37
Q

Alkenes are ____ hybridized

A

sp2

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38
Q

Are alkenes polar? Hydrophobic or hydrophilic?

A

Nonpolar and hydrophobic

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39
Q

What is the geometry of alkenes?

A

Planar

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40
Q

Are alkenes EW or ED?

A

Can be either depending on substituents

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41
Q

Alkynes are ____ hybridized

A

sp

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42
Q

Are alkynes polar? Hydrophobic or hydrophilic?

A

Nonpolar and hydrophobic

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43
Q

Are alkynes EW or ED?

A

Mostly EW

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44
Q

Alkanes and alkenes can only form _____ interactions

A

Van der Waals

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45
Q

Can alkanes and alkenes form bonds with water?

A

No, so they are not water soluble

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46
Q

What does a larger and more branched alkyl chain mean for hydrophilicity and lipophilicity?

A

Less hydrophilic and more lipophilic

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47
Q

Halogenated hydrocarbons are generally ___ hydrophilic than the alkyl form

48
Q

Which halogen is the most electronegative and which is the least?

A
  • Most = F

- Least = I

49
Q

Which halogen is the smallest and which is the largest?

A
  • Smallest = F

- Largest = I

50
Q

Are halogenated hydrocarbons hydrophobic or hydrophilic?

A

Hydrophobic

51
Q

Are halogens of saturated hydrocarbons EW or ED by induction?

52
Q

When is OH ED?

A

Through resonance

53
Q

When is OH EW?

A

Through induction

54
Q

Are alcohols H-bond donors or acceptors?

55
Q

What happens to alcohol solubility when the length of a hydrocarbon increases?

A

Solubility decreases, but it depends on the position of the OH

56
Q

Are phenols or aliphatic alcohols more acidic?

57
Q

Are alcohols acidic?

A

Not really

58
Q

What is the typical pKa of phenols?

A

9-10, but depends on other substituents

59
Q

Are aromatic hydrocarbons hydrophobic or hydrophilic when they are unsubstituted?

A

Hydrophobic

60
Q

Is a sulfhydryl group (-SH) polar?

A

Yes, but only weakly polar

61
Q

Is SH ED or EW?

62
Q

Is R-SH or R-OH more acidic?

A

R-SH because it is more willing to give up it’s proton

63
Q

Are ethers polar?

A

Yes, weakly

64
Q

Are thioethers polar?

A

Yes, weakly

65
Q

Is alkoxy (-OR) EW or ED?

66
Q

Is thioalkoxy (-SR) EW or ED?

67
Q

Is sulfoxide ED or EW?

A

Always EW because it is a sulfur w/ a double bonded oxygen

68
Q

Does sulfoxide have a lone pair of electrons?

69
Q

Is sulfoxide polar?

A

Yes, highly

70
Q

Is sulfone ED or EW?

A

Always strongly EW

71
Q

Is sulfone polar?

A

Highly polar

72
Q

Acetone is ___ hybridized

73
Q

Is a carbonyl (C=O) polar?

74
Q

Are aldehydes and ketones EW or ED?

75
Q

What are aldehydes and ketones in rapid equilibrium with and what does this form?

A
  • In equilibrium with alcohol

- Forms hemiacetal and hemiketal

76
Q

Are amines polar?

77
Q

What types of interactions can amines form?

A
  • H-bonds
  • Dipole-dipole
  • Ion-dipole
78
Q

Is the neutral form of amine EW or ED?

A
  • ED through resonance

- EW through induction

79
Q

Is the nitrogen of amine acidic or basic?

A

Basic, so it can accept a proton

80
Q

What types of interactions can carboxylic acids form?

A
  • H-bonds
  • Dipole-dipole
  • Ion-dipole
81
Q

Are carboxylic acids polar?

82
Q

Are carboxylic acids EW or ED?

A
  • EW when in neutral form

- ED when in anion form

83
Q

Should a carboxylic acid be used when doing a substitution in a molecule that is EW?

A

No, because at physiological pH it readily deprotonates, making it ED

84
Q

Are esters polar?

85
Q

What types of interactions can esters form?

A

Only H-bonds with water

86
Q

Are esters EW or ED?

87
Q

What is important to note about RCOOR’ (ester)?

A
  • Susceptible to hydrolysis
  • Catalyzed by esterases
  • Frequently used a prodrug to facilitate the absorption of carboxylic acid drugs
88
Q

Are amides polar?

89
Q

What types of interactions can amides form?

A
  • H-bonds with water

- Dipole-dipole

90
Q

Are amides EW or ED?

91
Q

Is the N of RCONR2 (amide) basic?

A

No because the lone pair of electrons forms a resonance structure and is not available to accept a proton

92
Q

Are amides acidic or basic at physiological pH?

93
Q

Nitriles and carbonates have properties similar to _____

94
Q

Carbamates have properties between ____ and _____

A

Esters and amides

95
Q

Ureas have properties similar to _____ and are ___ stable

A
  • Amides

- Very

96
Q

Are aminidines and guanidines polar?

A

Highly polar

97
Q

What types of interactions can aminidines and guanidines form?

A
  • H-bonds
  • Dipole-dipole
  • Ion-dipole with water
98
Q

Are aminidines and guanidines EW or ED in the neutral form?

A
  • Aminidines are EW

- Guanidines are weakly ED and weakly EW due to the electronegativity of nitrogen

99
Q

Are aminidines and guanidines EW or ED in the ionized form?

A
  • Aminidines are EW whether negative or positive

- Guanidines are EW whether negative or positive

100
Q

Are aminidines and guanidines more or less basic than amines?

101
Q

What should you use if you want to add something to a molecule that is EW?

102
Q

Is a nitro polar?

A

Only slightly

103
Q

Are nitros EW or ED?

104
Q

Can the negative O on a nitro accept an H+?

105
Q

Sulfonic acids have properties similar to ______

A

Carboxylic acids

106
Q

Are sulfonic acids EW or ED?

107
Q

Are sulfonic acids or carboxylic acids more polar?

A

Sulfonic acids

108
Q

Sulfonamides have properties similar to _____

109
Q

Are sulfonamides EW or ED?

110
Q

Are sulfonamides or amides more acidic?

A

Sulfonamides

111
Q

Which molecules are commonly involved in heterocycles?

A

N, O, or S

112
Q

What are the requirements for a compound to be aromatic?

A
  • Cyclic
  • Planar
  • Delocalized conjugated
  • # of electrons in p orbitals capable of forming pi bonds satistfies 4n + 2
113
Q

What is needed for a compound to be considered delocalized conjugated?

A
  • Every atom in ring has p orbital that can form pi bonds

- Every atom is sp2 hybridized

114
Q

Are the interactions between aromatic rings considered dipole-dipoles interactions?

A

No, because an aromatic ring has more than 2 poles

115
Q

What are the 3 types of aromatic/pi stacking interactions?

A
  • T-shaped or edge to face
  • Parallel displaced
  • Sandwich

Medicinal Chemistry (14 decks)

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