Brainscape's Knowledge GenomeTM

Browse over 1 million classes created by top students, professors, publishers, and experts.


See full index

Med Chem > Lecture 1 (Intro to MedChem) > Flashcards

Lecture 1 (Intro to MedChem) Flashcards

1
Q

What is a lead compound?

A

A lead compound is like the first draft of a drug. It has the correct pharmacological effect but it is not perfect. It most likely needs to be tweaked to obtain the most optimal and effective drug function.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

How are drugs improved?

A

By using a SAR (structure activity relationship) we can turn lead compounds into safe and effective drugs.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

Two types of SARs?

A

Quantitative (QSAR)
Qualitative (SAR)
-this is the only one we are concerned with

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

How is a QSAR used?

A

Uses a mathematical relationship between PHYSICOCHEMICAL PROPERTIES to their pharmacological activity to predict the most potent structure.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

Why won’t we be studying QSAR?

A

Because it cannot easily be extrapolated to new drugs. It requires extensive research for each drug.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

How is a SAR used?

A

-uses the relationship of the STRUCTURE (arrangement of the functional groups) and the pharmacological activity of the drug

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

What are the chemical properties of drugs we need to consider?

A
  • placement of covalent bonds
  • EN
  • electron effects of functional groups
    - ED (electron donating)
    - EW (electron withdrawing)
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

What drug properties are going to be affected by different things?

A
  • potency absorption
  • distribution
  • metabolic profile
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

Describe sigma bonds

A
  • single bonds
  • formed by hybrid orbitals
  • free rotation around this bond
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

Describe pi bonds

A
  • double bonds
  • formed by overlapping P orbitals
  • no free rotation around this double bond
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

Define EN

A

ability to attract electron density

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

How does EN increase on the periodic table?

A

to the right and up it increases

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

What 2 ways can electron density move through a molecule?

A
  • resonance

- induction

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

Define resonance

A

movement of electron density through pi bonds (conjugated system)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

Every 1st bond is ____?

A

sigma

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

Every 2nd or 3rd bond is ___?

A

pi

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

What are sigma bonds made from?

A

hybridized orbitals (sp)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

What are pi bonds made from?

A

leftover p orbitals

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

Define induction

A

movement of electron density through sigma bonds (saturated carbons)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

How do you determine whether a functional group with be ED or EW?

A

Depends on:

  • EN
  • presence of lone pair electrons
  • multiple bonds (geometry of the molecule)
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

Electronegative atoms with a lone pair (excluding halogens) are __ through _________.

A

ED

resonance

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

Alkyl groups - the more branched, the more _____.

A

donating

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

Attached group with a double bond O or N or triple bond N are __ through __________.

A

EW

resonance

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
24
Q

pKa _____ for acids

A

low (inverse of Ka)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
25
Q

Ka ____ for acids

A

high (if they dissociate there is more of the ions than the acid - so a bigger number/ smaller number = high number)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
26
Q

pKa ____ for bases

A

high (inverse of Ka)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
27
Q

Ka ______ for bases

A

low (bases don’t like to dissociate so there would be less of the ions than the base - small number/big number = low number)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
28
Q

Ratio of ionization of a weak acid is what ratio?

A

[HA] / [A-]

unionized: ionized

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
29
Q

Ratio of ionization of a weak base is what ratio?

A

[HB+] / [B]

ionized: unionized

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
30
Q

To maximize ionization of HA to A-

A

pH > pKa

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
31
Q

To minimize ionization of HA to A-

A

pKa > pH

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
32
Q

To maximize ionization of B to HB+

A

pKa > pH

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
33
Q

To minimize ionization of B to HB+

A

pH > pKa

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
34
Q

We use pKa to measure ___ ________.

A

drug ionization

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
35
Q

We always assume the solvent is _____?

A

WATER BITCHES

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
36
Q

When we talk about the pKa of a base we will most likely be talking about ??

A

primary, secondary, or tertiary amines

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
37
Q

What is the difference between primary, secondary, and tertiary amines?

A

Primary:
The N is attached to 1 R group and 2 H’s

Secondary:
The N is attached to 2 R groups and 1 H

Tertiary:
The N is attached to 3 R groups

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
38
Q

How does the scale of basicity go for amines?

A

Secondary > Primary > Tertiary

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
39
Q

What is a substituent?

A

-an atom or group of atoms substituted in place of a HYDROGEN on the parent organic compound

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
40
Q

Describe alkanes

A

-tetrahedral
-sp3 hybrid
-bond angle 109.5
C-C bond length 1.5A
-non-polar (hydrophobic)
-ED ALWAYS

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
41
Q

Describe alkenes

A

-planar
-sp2 hybrid
-bond angle 120
C=C bond length 1.3A
-non-polar (but depends what R groups are)
-usually ED but can be EW depending on substituents

42
Q

Describe alkynes

A
  • sp hybrid
  • bond angle 180
  • C=-C (triple bond) bond length 1.2A
  • non polar (hydrophobic)
  • mostly EW
43
Q

Are alkanes and alkenes water soluble?

A

No way jose

44
Q

What happens when an alkane or alkene gets larger or more branched?

A

Becomes less hydrophilic or more lipophilic

45
Q

Halogenated hydrocarbons are generally less _____ than the alkyl form.

A

hydrophilic

46
Q

Halogenated hydrocarbons are ______.

A

hydrophobic

47
Q

Halogens on saturated hydrocarbons are ___ by _______.

A

EW

induction

48
Q

Why are alcohols more water soluble?

A

They have an OH group (hydroxyl) which increases polarity and therefore makes it more water soluble because water is also a polar molecule.

49
Q

Describe the hybridization and geometry of alcohols

A

sp3 hybridization

tetrahedral

50
Q

Alcohols from bonds with water through what type of bond?

A

Hydrogen bond

51
Q

How is an OH ED?

A

through resonance

52
Q

How is an OH EW?

A

through induction

53
Q

T or F: an alcohol only accepts hydrogen bonds

A

FALSE

alcohols are H bond donors and acceptors

54
Q

Why do alcohols have a permanent dipole?

A

EN oxygen
positive hydrogen

*those two bad boys result in a permanent freaking dipole

55
Q

With increasing length of hydrocarbon chain on an alcohol - how does that affect solubility?

A

decreases solubility

56
Q

Are alcohols very acidic?

A

NO WAY JOSE

57
Q

Does alcohol solubility depend on location of OH?

58
Q

Describe a phenol

A

-special type of alcohol

59
Q

Are phenols generally more acidic (more acidic means LOWER pKa) than aliphatic alcohols?

*slide 37

A

you bet your ass they are :D

60
Q

aromatic hydrocarbons are ________

A

hydrophobic

61
Q

SH (sulfhydryl) groups are ALWAYS __?

A

ED (sulfur is not very EN so it’s not going to withdraw - it will donate)

62
Q

SH group is _____ polar

63
Q

RSH is more _____ than ROH

64
Q

R-O-R is a ??

65
Q

R-S-R is a ???

66
Q

ethers and thioethers are weakly _____

67
Q

SR (thioalkoxy) is ____

68
Q

OR (alkoxy) is ____

69
Q

sulfoxide is always ___

70
Q

sulfone is always __

71
Q

Describe the hybridization and geometry of aldehydes and ketones

A

sp2 hybridization

planar

72
Q

aldehydes and ketones are always __

A

EW (they have an oxygen which is highly EN) - so therefore it will withdraw electrons

73
Q

aldehydes and ketones are in rapid equilibrium with ____ to form hemiketals and hemiacetals

74
Q

_____ have an sp3 tetrahedral N centre

75
Q

Are amines basic or acidic?

76
Q

Are amines polar?

77
Q

The N of amines are basic due to what?

A

free lone pair of electrons

78
Q

describe the hybridization and geometry of carboxylic acids (RCOOH)

A

sp2

planar

79
Q

Are carboxylic acids polar?

80
Q

neutral form of carboxylic acids are ____

81
Q

anionic form of carboxylic acids are ____

82
Q

Are esters (RCOOR) polar?

83
Q

Are esters (RCOOR) ED or EW?

84
Q

esters are susceptible to _____

A

hydrolysis

85
Q

What are esters frequently incorporated for?

A

To facilitate absorption of carboxylic acid drugs (they act as a pro drug)

86
Q

Describe hybridization and geometry of amides

A

sp2

planar

87
Q

are amides polar?

A

heck yes (napoleon dynamite voice)

88
Q

Is the N of an amide (RCONHR) basic?

A

NO (because lone pair of electrons forms resonance structure and therefore is not available to accept a proton)

  • N of amine = basic
  • N of amide = not basic
89
Q

The H of RCONHR (amide) is usually ___?

A

only very weakly acidic

90
Q

Are amidines and guanidine’s polar?

91
Q

In neutral form amidines are ___

92
Q

In neutral form guanidine’s are ___?

A

weakly EW and weakly ED due to electronegative nature of the N

*see slide 48 for details of structure

93
Q

In ionized form, both amidines and guanidine’s are ___

94
Q

Are amidines and guanidine’s less basic than amines?

A

No, they are more basic.

95
Q

Are Nitro (RNO2) highly EW or ED?

A

EW all the way

96
Q

Is the negative charge on the O in a nitro (RNO2) able to accept a proton?

A

no way man

97
Q

Describe hybridization and geometry of sulfonic acids and sulfonamides

A

sp3

tetrahedral

98
Q

T or F: sulfonic acids and sulfonamides are highly polar and EW

A

true true true

99
Q

Heterocycles usually contain what 3 elements?

A

S, O, and N

100
Q

Drugs with a 3 or 4 membered ring (heterocycle) are usually ???

A

strained and unstable (like me after a night of drinking)

101
Q

What are the requirements for a structure to be aromatic?

A

cyclic
planar
4n+2
delocalized conjugated (every atom in the ring has p orbitals capable of forming pi bonds)

Med Chem (11 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2025 Bold Learning Solutions. Terms and Conditions