Functional Group Charactristics and Roles Flashcards

1
Q

Functional group

A

structural component of a drug molecule with one or more atoms

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2
Q

Which properties do functional groups influence?

A

solubility
route of admin
ability of drug to bind to its target
mechanism of action
route of metabolism and elimination
duration of action
suitability for specific use
tendency to cause ADRs or drug interactions

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3
Q

You can alter functional groups to ?

A

enhance activity
increase absorption
decrease adverse effects
provide therapeutic benefits

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4
Q

What does SAR stand for?

A

structure activity relationship

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5
Q

What are the 3 chemical effects that functional groups have?

A

electronic
solubility
steric

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6
Q

Is it possible to change just one of the chemical properties of a functional group?

A

no

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7
Q

What do effects of a functional group depend on?

A

the environment surrounding it

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8
Q

electronic effect

A

ability to donate or withdraw electrons from adjacent atoms or functional groups

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9
Q

Resonance

A

when electrons are shared among a group of atoms that have adjacent double bonds and lone pairs of electrons

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10
Q

Intrinsic Inductive Effect

A

ability of atom/functional group to attract electrons towards itself and away from other atoms/functional groups

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11
Q

A higher electronegativity indicates?

A

a greater ability to attract electrons

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12
Q

Oxygen inductively attracts electrons from all other atoms except for?

A

F

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13
Q

Oxygen, nitrogen, and all 4 halogens will inductively attract electrons from?

A

carbon and hydrogen

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14
Q

What are some examples of electron donating functional groups?

A

aromatic hydroxyl
aromatic ether
aromatic amine
aromatic thiol
ionized acidic group
alkyl group

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15
Q

Negatively charged functional groups can donate electrons through ?

A

induction

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16
Q

Nucleophilic functional groups contain ?

A

either a negative charge or a lone pair of electrons

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17
Q

Examples of electron withdrawing groups

A

halogens
trifluoromethyl
ionized basic group
hydroxyl
sulfhydryl or thiol
ether
nitrile group
nitro group
aromatic heterocyclic
aldehyde
amide
ester
sulfonamide

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18
Q

When hydroxyl, sulfhydryl, and ether groups are not adjacent to either an aromatic ring or double bond system they will act as?

A

electron withdrawing groups

19
Q

Electrophilic functional groups contain?

A

positive charges, a conjugated double bond system, or a good leaving group

20
Q

Overall water/lipid solubility of drug molecule is equal to ?

A

the sum of the contributions of each functional group

21
Q

What properties contribute to water solubility of functional groups?

A

ability to ionize and form hydrogen bonds

22
Q

Ionization xxx the water solubility of a drug

A

increases

23
Q

Examples of acidic functional groups

A

carboxylic acid
beta-dicarbonyl
imide
sulfonamide
sulfonylurea
phenol
sulfonic acid
phosphonic acid

24
Q

Examples of basic functional groups

A

primary, secondary, and tertiary aliphatic amines
alicyclic amine
imine
amidine
guanidine
hydrazine
primary aromatic amine
heterocyclic nitrogen (imidazole)
heterocyclic nitrogen (quinoline)

25
Q

Which atom can serve as a bridge between electronegative atoms?

A

hydrogen

26
Q

Examples of hydrogen bond acceptors only

A

ketone
ester
thioether
heterocyclic nitrogens- 6 membered
fluorine
ether

27
Q

Examples of hydrogen bond donors only

A

heterocyclic nitrogen - 5 membered

28
Q

Examples of hydrogen bond acceptors and donors

A

phenol
amide
primary, secondary, and tertiary hydroxyls
thiol
carbamate
urea
primary and secondary unionized amines
unionized carboxylic acids

29
Q

Lipid solubility functional groups lack the ability to

A

either ionize or form hydrogen bonds

30
Q

Examples of lipid soluble functional groups

A

aromatic rings and ring systems
alkyl chains
alicyclic rings
alkenes
alkynes
halogens

31
Q

Which functional group can be viewed as either water or lipid soluble based on the groups attached to them?

A

Esters

32
Q

Can 2 atoms/functional groups occupy the same space?

A

no

33
Q

Steric effects contribute to the xxx of the drug molecule.

A

shape

34
Q

What of each functional group must be able to be accommodated for by receptor binding sites?

A

size and shape

35
Q

What are some results of steric effects?

A

increased selectivity
enhanced binding
alteration of metabolism

36
Q

The same functional groups can provide xxx effects on different drug molecules

A

different

37
Q

Can a single functional group serve more than one purpose?

A

yes

38
Q

What is an isostere?

A

group of molecules or ions that have the same number of valence electrons and have chemical or physical similarities

39
Q

Monovalent isosteres

A

CH3
NH2
OH
F
Cl
SH
Br
I

40
Q

Bivalents Isosteres

A

-CH2-
-O-
-NH-
-S-
-CH2-r-CH2

41
Q

Trivalent Isosteres

A

-CH=
-N=
-P=
-CH2-R=CH

42
Q

Annular Equivalent Isosteres

A

aromatic ring systems
-CH=CH-
-NH-
-O-
-S-

43
Q

Advantages of Isosteres

A

decreased metabolism; enhanced duration; allows oral use
increased bioavailability
conversion of metabolites to antimetabolites
development of antagonists/inhibitors from agonists/ substrates
enhanced solubility
increased receptor binding
separate activities
me-too drugs