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Medicinals Organic Chemistry > Physicochemical > Flashcards

Physicochemical Flashcards

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1
Q

interdisciplinary science at the intersection of organic chemistry, biochemistry (biochemistry), computational chemistry, pharmacology, molecular biology and physical chemistry

A

Medicinal Chemistry

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2
Q

Involved with the identification, design, synthesis and development of new drugs that are safe and suitable for therapeutic use in humans and pets

A

Medicinal Chemistry

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3
Q

Study of marketed drugs, their biological and their quantitative structure-activity relationships (QSARs)

A

Medicinal Chemistry

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4
Q

Studies how chemical structure influences biologic activity

A

Medicinal Chemistry

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5
Q

Studies How the molecular and physicochemical properties of the molecule influences the drug’s pharmacokinetics (ADME) and pharmacodynamics (what the drug does to the body).

A

Medicinal Chemistry

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6
Q

how functional groups present within the molecule influence its acid-base properties, water solubility, partition coefficient, crystal structure, stereochemistry, and ability to interact with biologic systems, such as enzyme active sites and receptor sites

A

Physicochemical

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7
Q

relationship of how structural features of the molecule contribute to, or take away from, the desired pharmacologic properties

A

Structure-activity relationships (SARs)

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8
Q

influences the biologic activity of chemical entities and that alterations in structure produce changes in biologic action.

A

Molecular structure

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9
Q

“one chemical group gives one biological action”

A

Postulate

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10
Q

developed the concept of drug receptors

A

Ehrlich (Paul Ehrlich)

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11
Q

Interaction of the chemical with the cell surface “side chains” produces a what

A

Toxic effect

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12
Q

Selectivity permitted eradication of disease states without significant harm coming to the organism being treated.

A

Selective Toxicity (albert)

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13
Q

The underlying principle of medicinal chemistry

A

Structure-Activity Relationships

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14
Q

T or F. Similar molecules exert similar biologic action in a qualitative sense

A

T. SAR

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15
Q

groups within a specific structure are important for its pharmacologic activity and how these groups can be modified to produce more potent, mode selective, and safer compounds

A

Functional Groups

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16
Q

Example of drugs with structural similarity:

A

PABA and sulfanilamide

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17
Q

How can drug molecules exhibit their pharmacologic activity?

A

By interacting with a biologic target , typically a receptor, enzyme, nucleic acid, or excitable membranes or other biopolymer

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18
Q

The relative fit of each drug molecule with its target is a function of a number of what

A

Physicochemical properties

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19
Q

What are the three physicochemical qproperties

A

1.Acid-base chemistry and related ionization
2. Functional group shape and size
3. Three dimensional-spatial orientation

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20
Q

are natural polymers produced by the cells of living organisms.

A

Biopolymers

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21
Q

consist of monomeric units that are covalently bonded to form larger molecules.

A

Biopolymers

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22
Q

Most appropriate to explain and predict acid-base behavior

A

Bronsted-Lowry acid-base theory

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23
Q

When an acid gives up a proton to a base, it is converted to its what

A

Conjugate base

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23
Q

any substance capable of yielding a proton (H+)
- Based on BLABT

A

Acid

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24
Q

any substance capable of accepting a proton
- according to BLABT

A

Base

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25
Q

When a base accepts a proton, it is converted to its whatt

A

Conjugate acid

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26
Q

T or F. When a basic functional group is converted to the corresponding conjugate acid, it too become unionized.

A

F. Ionized

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27
Q

Functional groups that cannot give up or accept a proton are considered to be ___ with respect to their acid-base properties.

A

“neutral” (or “nonelectrolytes”)

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28
Q

Acids and Conjugate Base
Phenol (9-11)

A

Phenolate

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29
Q

Sulfonamide (9-10)

A

Sulfonamidate

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30
Q

Imide (9-10)

A

Imidate

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31
Q

Alkylthiol (10-11)

A

Thiolate

32
Q

Thiophenol (9-10)

A

Thiophenolate

33
Q

N-Arylsulfonamide (6-7)

A

N-Arylsulfonamidate

34
Q

Sulfonimide (5-6)

A

Sulfonimidate

35
Q

Alkylcarboxylic acid (5-6)

A

Alkylcarboxylate

36
Q

Arylcarboxylic acid (4-5)

A

Arycarboxylate

37
Q

Sulfonic acid (0-1)

A

Sulfonate

38
Q

Common basic functional groups and conjugate acid
Arylamine

A

Arylammonium

39
Q

Aromatic amine (5-6)

A

Aromatic ammonium

40
Q

Imine (3-4)

A

Iminium

41
Q

Alkylamines

A

Alkylammonium

42
Q

Amidine

A

Amidinium

43
Q

Guanidine

A

Guanidinium

44
Q

Neutrals

A

Alkyl Alcohol
Ether
Ester
Sulfonic acid ester
Amide
Diarylamine
Nitrile
Quaternary ammonium
Amine oxide
Ketone and aldehyde
Thioether
Sulfoxide sulfone

45
Q

A molecule can contain multiple functional groups with acid-base properties and, therefore, can possess both acidic and basic character. T or F

A

T

46
Q

Examples of molecule containing multiple functional groups with acid-base proteins

A

Ciprofloxacin, (a fluoroquinolone antibacterial agent)

47
Q

are weakly basic
- Do not contribute significantly to the acid-base properties

A

Arylamines

48
Q
  • Accept a proton
A

Secondary alkylamine

49
Q
  • Donate a proton
A

Carboxylic acid

50
Q

Can act as an acid and base

A

Amphoteric

51
Q

one can predict whether a molecule is going to be predominantly ionized or un-ionized at a given pH by knowing what

A

acidity/basicity of a functional group

52
Q

T or F Ionized (or charged) drugs are not absorbed as efficiently as un-ionized drugs are

A

True

53
Q

Principle for this: a weak acid will be absorbed primarily in the acidic environment; whereas, a drug that is a weak base will be absorbed in the alkaline environment (small intestines)

A

Like dissolves like

54
Q

greatly affects the routes of administration as well as absorption, distribution and elimination

A

Water

55
Q

Potential for hydrogen bond formation
Ionization of one or more functional groups

A

Water solubility of a molecule

56
Q

Acceptance of a hydrogen bond

A

increases the hydrophilic (water-loving) nature of the molecule

57
Q

groups that cannot form hydrogen bonds do not enhance hydrophilicity

A

contribute to the hydrophobic (water-fearing) nature of the molecule

58
Q

Another type of interaction that plays an important role in determining water solubility, which occurs between either a cation and the partially negative charged atom found in a permanent dipole

A

Ion-dipole interaction

59
Q

Ion dipole interaction occurs between either a what and a what

A

cation and a partially negative charged atom found in a permanent dipole

60
Q

approach in predicting the water solubility of molecules based on the carbon-solubilizing potential of several functional groups.

A

Empiric approach

61
Q

If the solubilizing potential of the functional group exceeds the total number of carbon atoms present, then the molecule is considered to be what

A

water soluble

62
Q

Opioid analgesic that contains three functional groups that contribute to water solubility

A

Anileridine

63
Q

If Solubilizing potential is less than the total number of carbons,

A

insoluble in water

64
Q

Molecules that contain the same number and kinds of atoms
The same arrangement of bonds, but different three-dimensional shape arrangement of atoms in space

A

Stereoisomers

65
Q

2 types of stereoisomers

A

Enantiomers and Diastereomers

66
Q

Pairs of molecules for which three-dimensional arrangement of atoms represents non-superimposable mirror images.

A

Enantiomers

67
Q

All of other stereoisomeric compounds that are not enantiomers
Compounds that contain double bonds (geometric isomers) and ring systems
Exhibit different physicochemical properties, including, but not limited to, melting point, boiling point, solubility, and chromatographic behavior

A

Diastereomers

68
Q

Empiric approach to predicting the water solubility of molecules based on the _______________ of several functional groups.

A

carbon-solubilizing potential

69
Q

% solubility of water solubility

A

1%

70
Q

There drugs are not absorbed as efficiently as un-ionized drugs are.

A

Ionized or charged drugs

71
Q

T or F weak acid will be absorbed primarily in the acidic environment; whereas, a drug that is a weak base will be absorbed in the alkaline environment (small intestines)

A

T

72
Q

Example of an alkaline environment

A

Small intestines

73
Q

ph of stomach

A

1 - 3.5

74
Q

pH of Colon

A

5.6 -7

75
Q

completely donate (dissociate) or accept a proton in aqueous solution

A

Strong acids and bases

76
Q

Act as an acid or a base, depending on the prevailing pH of the solution.

A

AMPHOTERIC

77
Q
A

Medicinals Organic Chemistry (3 decks)

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