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z F1: Med Chem > Exam 1 > Flashcards

Exam 1 Flashcards

1
Q

What are the principles on which modern drug development and discovery is based

A

Absorption: how much gets into body
Distribution: where drug ends up
Metabolism: body deal with substance
Excretion: how much it gets rid of
Toxicity: will it hurt

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2
Q

High protein binding drugs are __________ drugs

A

lipophilic

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3
Q

Consequence of high protein binding is

A

drug-drug interactions

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4
Q

Consequence of hERG

A

drugs bind to hERG can cause fatal arrhythmias

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5
Q

The behavior of all drugs is determined by their chemical properties which is due to their _________ ______

A

functional groups

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6
Q

Drugs get the _____ number on alicyclic rings

A

lowest, the substituents are then counted lowest from there

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7
Q

The three most common heteroatoms in drugs are

A

N, S, O
highest priority is based on molecular weight

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8
Q

Alpha and Beta are used to indicate a carbon atom that is adjacent to _____

A

C=O or a heteroatom

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9
Q

Omega is used to indicate the ____ of an alkyl chain

A

end

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10
Q

On a molecule which side is the alpha side and which is the beta side

A

Beta side is on top with bold lines
Alpha side on the bottom with dashed lines

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11
Q

The same functional group can serve _______ roles depending on the location in the drug

A

different

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12
Q

Each functional group can serve _____ roles at the same time

A

several

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13
Q

What are the three major chemical properties to consider when evaluating functional groups

A

Electronic effect (electron withdrawing or donating)
Solubility
Steric (how big is it)

-Each functional group effects all of the factors
-The overall effect of each group depends on other functional groups surrounding it

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14
Q

Negatively charged groups can donate electrons through

A

induction

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15
Q

Functional groups with a lone pair can donate electrons through

A

resonance

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16
Q

alkyl groups can donate electrons through

A

induction

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17
Q

Electron withdrawing groups

A

positive charged groups can pull e- via induction
When alcohol, ether, thiol groups are NOT adjacent they are EWG
Halogens are withdrawing groups

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18
Q

Solubility effects are based on the ability of a functional group to

A

Enhance interactions with water (hydrophobic or lipophilic)
Enhance interactions with lipids (hydrophobic or lipophilic)

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19
Q

What two major properties enhance the water solubility of a functional group

A

the ability to ionize (atom to become charged)
ability to form hydrogen bonds

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20
Q

Acids donate their protons ____ water
Bases accept protons ____ water

A

Acids: to
Bases: from

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21
Q

Prototype for determining interactions with the aqueous environment, through the interaction of hydroxyls to form _______

A

H-bonds

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22
Q

General points for alcohols groups: ____ participate in IMF, ____ interact with with water

A

can
can

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23
Q

While the alcohol group interacts well with a water molecule, the overall stability of ROH is dependent on the _____ of the hydrocarbon side chain attached to that alcohol ________

A

size
R-group

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24
Q

The ________ effects of the carbons will counteract the __________ effects of the alcohol

A

hydrophobic
hydrophilic

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25
Q

As the length of the hydrocarbon side chain alcohol group increases, the _________ nature of the molecule decreases

A

hydrophilic

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26
Q

In thiols the S atom is ______ than O atom so it can better stabilize a negative charge

A

larger

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27
Q

Thiols can be ________ especially if attached to an aromatic ring or in an enzyme active site

A

ionized

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28
Q

The ability of the thiol SH to H-bond is ______ than an alcohol

A

weaker, they are not as polar

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29
Q

Can ketones and aldehydes h-bond, are they polar

A

yes
yes due to carbonyl

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30
Q

Esters increased _______ over the both alcohol and acid parent, but still polar due to dipole of the carbonyl and oxygen in the functional group

A

lipophilicity

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31
Q

Esters can be used to _______ absorption following oral admin of some drugs, relies on hydrolysis of ester to release active form in the blood stream

A

increase

32
Q

Are amides ionizable groups in the body? If so are they acids or bases and why?

A

Not readily ionizable because resonance prevents ionization
amides have carbonyl and amines do not
lone pair of nitrogen is not available = not a base

33
Q

Amides

A

-found in peptides
-less lipid solubility than esters (more hydrophilic)
-high degree of H-bonds
-As hydrocarbon portion of amide increases so does lipophilic nature

34
Q

Carbamates

A

fusion between an amide and an ester
behave more like an amide than an ester

35
Q

Ureas

A

look like a fusion between 2 amides
properties similar to amides, perhaps a bit more polar

36
Q

Ethers

A

H-bond acceptor
form weak H-bonds from O
more polar than alkane

37
Q

Cyclic ethers

A

locks in 109 degree and enhance dipole, more polar as result

38
Q

Lipophilicity ______ as the number of carbons increase

A

increases

39
Q

Non polar functional groups lack to ability to _______ and ________

A

ionize and H-bond

40
Q

Alkyl groups (ethyl, methyl etc)

A

Are the most lipophilic of the functional groups
increase size = increase lipophilicity

41
Q

Alkenes, aromatic groups, heteroaromatic compounds

A

Have pi system, allows for induction
Interact with similar groups on target molecules
Can be substituted with heteroatoms, remain aromatic

42
Q

Halides

A

-Hydrophobic
-Electron withdrawing increases as size of atom decreases
-Effect on pKa when added carbons adjacent to acid/base functional groups

43
Q

Fluorine halide

A

size=hydrogen atom
used in place of hydrogen to increase a dipole

44
Q

Chlorine halide

A

larger in size than fluorine, 1/2 that of methyl
improve interaction of an aromatic group with an aromatic binding site or to block metabolism on aromatic groups

45
Q

Bromine halide

A

larger than chlorine, smaller than methyl
improve interaction of aromatic group, block metabolism on aromatic groups

46
Q

Iodine halide

A

size=methyl
mimix a methyl group in size, but have an opposite electronic effect than methyl

47
Q

Nitroesters, nitrates, nitrogroups on alkanes

A

similar to halides

48
Q

functional groups that are ______ will have the strongest interaction with water, and the least with a lipid

A

charged

49
Q

functional groups that are polar but can’t h-bond will have properties __________ aqueous and lipid loving

A

in between

50
Q

combining a polar functional group with a number of atoms of a non-polar functional group will result in a ________ of properties for the ______ molecule

A

composite
whole

51
Q

Key features of acids

A

The presence of a hydrogen that can dissociate to form a proton
The ability of the other atoms to delocalize the resulting negative charge (via resonance)

52
Q

The ionized form of a carboxylic acid is known as a _________

A

carboxylate

53
Q

If the R group is electron withdrawing it will stabilize the _____ and increase its _________

A

anion
acidity

54
Q

non-ionized carboxylic acid general points

A

-carboxylic acids are polar and can hydrogen bond when in protonated form
-are more polar than alcohols and will provide stronger interaction
-increase R-group length decreases water solubility and increases lipid solubility

55
Q

Are the majority of drugs in a ketone or enol form

A

enol

56
Q

The imide is an example of a(n) ______ nitrogen

A

acidic

57
Q

When groups have a similar shape, size, and electron density, they are ________ of each other

A

bioisosteres

58
Q

A regular alcohol has no resonance stabilization and therefore can not ________

A

ionize

59
Q

How many acidic protons does phosphonic acid have

A

2

60
Q

What is a key feature of a base

A

presence of a lone pair that can accept a proton
*ability of electrons to accept proton makes it stronger

61
Q

Steric bulk of groups _____ access to lone pair

A

hinder
-makes it more acidic

62
Q

Amines general points

A

-solubilize drugs as the free base or as water soluable slat of amine
-hold drug to target
-alkaline

63
Q

Why are aromatic amine less basic than aliphatic amines

A

Lone pair gets pulled into aromatic ring contributing to resonance while aliphatic can give lone pair to carbon

64
Q

What are amphoteric molecules

A

contain both acidic and basic functional groups

65
Q

Protonation occurs on the ___ hybridized nitrogen

A

sp2

66
Q

Sulfanaminde, sulfonyl urea, imide, tetrazole

A

acidic nitrogen containing functional groups

67
Q

amide, carbamate, urea, pyrrole, indole

A

neutral nitrogen containing funcitonal groups

68
Q

ionization = charge = ________ water solubility

A

increase

69
Q

________ drugs are more readily reabsorbed increasing their half life in body

A

neutral

70
Q

The degree to which acidic and basic functional groups are ionized depends on the ____ of the functional group in question and on the _____

A

pka
pH

71
Q

pKa provides no information about _____ a molecule will ionize. It will only indicate the degree to which it will occur

A

how

72
Q

When pH=pKa the solution …

A

50% acid and 50% base

73
Q

When pH is below the pKa

A

acid (neutral) > base (ionized)
protonated form > deprotonated form

74
Q

When pH is above pKa

A

base (ionized) > acid (neutral)
deprotonated > protonated

75
Q

AID your BUDdy

A

pH higher than pKa
acidic functional group, ionized form dominates
basic functional group, unionized form dominates

76
Q

BID on the AUDience

A

pH lower than pKa
basic functional group, ionized form dominates
acidic functional group, unionized form dominates

z F1: Med Chem (3 decks)

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