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MPharm Year 2 > Chemistry > Flashcards

Chemistry Flashcards

1
Q

Name this function group

A

Benzene derivative

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2
Q

Name this function group
X = F, Cl, Br or I

A

Haloalkane

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3
Q

Name this function group

A

Primary alcohol

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4
Q

Name this function group

A

Secondary alcohol

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5
Q

Name this function group

A

Tertiary alcohol

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6
Q

Name this function group

A

Ether

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7
Q

Name this function group

A

Primary amine

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8
Q

Name this function group

A

Secondary amine

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9
Q

Name this function group

A

Tertiary amine

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10
Q

Name this function group

A

Quaternary ammonium salt

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11
Q

Name this function group

A

Nitrile

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12
Q

Name this function group

A

Sulfide (thioether)

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13
Q

Name this function group

A

Sulfoxide

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14
Q

Name this function group

A

Sulfone

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15
Q

Name this function group

A

Sufonic acid

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16
Q

Name this function group

A

Thiol

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17
Q

Name this function group

A

Aldehyde

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18
Q

Name this function group

A

Ketone

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19
Q

Name this function group

A

Carboxylic acid

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20
Q

Name this function group

A

Ester

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21
Q

Name this function group

A

Primary amide

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22
Q

Name this function group

A

Secondary amide

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23
Q

Name this function group

A

Tertiary amide

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24
Q

What is a nucleophile?

A

Donate a pair of electrons to an electron deficient species.
Usually a pair of lone electrons or a pair of electrons from a pi bond

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25
Q

Common nucleophiles?

A

Water
Alcohol
Hydroxide ion
Carbonyl oxygen
Ammonia
Amine
Alkene benzene

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26
Q

What is an electrophile?

A

Electron pair acceptors. Either positively charged or contain an electron deficient atom within the functional group

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27
Q

Common electrophiles?

A

Carbonyl compounds
Acyl chloride
Acid anhydride
Aldehyde
Ketone
Ester
Carboxylic acid
Amide

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28
Q

Electronegativity of hydrogen?

A

2.20

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29
Q

Electronegativity of carbon?

A

2.55

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30
Q

Electronegativity of nitrogen?

A

3.04

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31
Q

Electronegativity of oxygen?

A

3.44

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32
Q

Electronegativity of fluorine?

A

3.98

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33
Q

Electronegativity of phosphorus?

A

2.19

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34
Q

Electronegativity of sulfur?

A

2.58

35
Q

Electronegativity of chlorine?

A

3.16

36
Q

Electronegativity of bromine?

A

2.96

37
Q

Electronegativity of iodine?

A

2.66

38
Q

Which nitrogen attaches to C1 in adenine base?

A

N on 5 membered ring, not near double bond

39
Q

Which nitrogen attaches to C1 in guanine base?

A

N on 5 membered ring, not near double bond

40
Q

Which nitrogen attaches to C1 in cytosine base?

A

N opposite NH2

41
Q

Which nitrogen attaches to C1 in thymine base?

A

N attached to a single carbon and C=O

42
Q

Which carbons are involved in the condensation reaction between the pentose sugar and the phosphate group?

A

OH on C3 and phosphate group on C5

43
Q

How is the sugar phosphate backbone bonded?

A

Through condensation reaction

44
Q

Bonds between base pairs?

A

2 hydrogen bonds between A-T
3 hydrogen bonds between G-C

45
Q

Function of topoisomerase II?

A

Relieves strain of unravelling DNA by cutting the long chain

46
Q

How does topoisomerase II work, in regards to chemistry?

A

Alcohol group attached to tyrosine acts as a nucleophile to attack the phosphate as it has lone pairs
The oxygens on the phosphate group are more electronegative making the phosphorus slightly positive so it is attacked by the nucleophile

47
Q

Structure of adrenaline?

A
48
Q

Bonding between adrenaline and its target?

A

Hydrogen bonding from secondary alcohol
Van der Waals from benzene ring
Ionic bond from amine

49
Q

Why does the amine in adrenaline undergo ionic bonding?

A

As it is 91% ionised at pH 7.4

50
Q

Functional groups in adrenaline?

A

Phenol
Secondary alcohol
Secondary amine

51
Q

Which enantiomer of adrenaline is more active?

A

R

52
Q

SARs of adrenaline?

A

1)Phenol involved in hydrogen bonding.
2) alcohol group in side chain involves in hydrogen bonding
3) R enantiomer is more active
4) ionic bonding from N+
5) larger substituents on N increases selectivity of B-receptors

53
Q

How to increase selectivity of adrenaline for b-receptors?

A

Larger substituents on the N

54
Q

Which phenol group on adrenaline can be substituted?

A

Meta

55
Q

How to make isoprenaline B-2 specific?

A

Add ethyl group to carbon bonded to nitrogen, creates isotharine

56
Q

Why modify phenol at meta position on adrenaline?

A

Cannot be recognised and therefore metabolised by COMT

57
Q

What is COMT?

A

Catecol-o-methyltransferase

58
Q

How to COMT work?

A

Adds methyl group to meta phenol on adrenaline so it cannot hydrogen bond to target

59
Q

What can salbutamol be synthesised from?

A

Aspirin

60
Q

Why is salmeterol longer acting?

A

It has large hydrophobic groups that increase its lipophilicity

61
Q

Types of chemotherapy that directly interacts with DNA?

A

Alkylating agents
Metallating agents
Intercalating agents
Topoisomerase poisons
Chain cutters
Chain terminators

62
Q

How does paclitaxel work?

A

Binds to tubulin to halt cell division cycle

63
Q

What does DNA contain?

A

Phosphate group
Nitrogen-containing base
2-deoxyribose sugar

64
Q

What is the primary structure of DNA?

A

The base sequence

65
Q

How do nucleotides join together?

A

Two nucleotides join together when OH on C3 group reacts with phosphate group on C5. A condensation reaction to form a phosphodiester bond

66
Q

What is the secondary structure of DNA?

A

A double helix structure with the sugar-phosphate backbone ionised and pointing outwards

67
Q

What is the tertiary structure of DNA?

A

Coiled into a compact 3D shape to fit into the nucleus, called supercoiling

68
Q

How do alkylating agents work?

A

Contain highly electrophilic groups that form covalent bonds with nucleophilic groups in DNA

69
Q

What kind of cross-linking do alkylating agents cause?

A

Interstrand

70
Q

Examples of alkylating agents?

A

Chlormethine
Melphalan
Uracil
Estramustine
Chlorambucil
Ifosfamide

71
Q

Nitrogen mustards react with which DNA base?

A

Guanine

72
Q

Why can melphalan be given orally?

A

It has an electron-withdrawing group making the nitrogen less susceptible to attack

73
Q

Which amino acid does melphalans structure mimic?

A

Phenylalanine

74
Q

Why does melphalan mimic phenylalanine?

A

To be recognised as an amino acid so it will be taken into the cell by transport proteins

75
Q

How does cisplatin work?

A

Activated in cells with low chloride ion concentrations
Chloro substituents replaced with water, forming positively charged species
Binds to DNA to cause intrastrand cross-linking

76
Q

Examples of metallating agents?

A

Cisplatin
Carboplatin
Oxaliplatin

77
Q

What kind of cross-linking do metallating agents cause?

A

Intrastrand

78
Q

How do intercalating agents work?

A

Contain planar ring systems which slip between layers of nucleic acid pairs and disrupt the shape of the helix

79
Q

Examples of intercalating agents?

A

Bleomycin
Proflavine
Dactinomycin

80
Q

How do chain cutters work?

A

Intercalating agents that cut strands of DNA and prevent DNA ligase from repairing damage

81
Q

Examples of chain cutters?

A

Drugs that contain calicheamicin such as gemtuzumab ozogamicin

82
Q

How do topoisomerase II poisons work?

A

Stabilise the covalent intermediate between DNA and topoisomerase II

83
Q

Examples of topoisomerase II poisons?

A

Etoposide
Teniposide

MPharm Year 2 (6 decks)

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