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MedChem Midterm 2 > Heterocycles Reversed > Flashcards

Heterocycles Reversed Flashcards

1
Q

saturated 8-membered heterocycles

unsaturated

A

-ocane

-ocine

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2
Q
A

azepine

-ine 7 membered UNSATURATED

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3
Q
A

benzoxazole

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4
Q
A

benzothiazole

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5
Q
A

cabapenems

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6
Q
A

pKa’s of

Pyridine

Pyridazine

Pyrimidine

Pyrazine

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7
Q
A

carbacephems

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8
Q
A

Aziridine

-idine for Nitrogens (3 membered staturated)

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9
Q
A

penam

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10
Q
A

tetrazole

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11
Q
A

morpholine

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12
Q
A

1,2-diazepane

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13
Q
A

cinnoline

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14
Q
A

cepham

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15
Q
A

Thiirane

-irane for 3 membered rings (saturated)

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16
Q
A

penams

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17
Q
A

adenine

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18
Q
A

isoxazole

1,2-oxazole

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19
Q
A

1,4-diazepane

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20
Q
A

quinoline

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21
Q
A

oxapenams

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22
Q
A

Order of Reactivity

Beta Lactams

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23
Q
A

furan

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24
Q
A

benzotriazole

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25
Q

Alcohol = 1

Amide = 1

imidazole = 1

pyrrole = 1

1*(primary) amine = 2

A

H-Bond Donors

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26
Q
A

pyridine

-ine 6 membered unsaturated

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27
Q

saturated 6-membered heterocycle

unsaturated (aromatic)

A

-inane

-ine

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28
Q
A

cephems

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29
Q
A

penems

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30
Q

saturated 5-membered heterocycles

unsaturated

saturated w/ NITROGEN

A

-olane

-ole

-olidine

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31
Q
A

purine

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32
Q
A

pyrrole

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33
Q
A

tetrahydrothiophene

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34
Q
A

thiophene

35
Q
A

1h-benzo[b][1,4]diazepine

36
Q
A

oxacephems

37
Q
A

isothiazole

1,2-thiazole

38
Q
A

1,2,3-triazole

39
Q
A

quinazoline

40
Q
A

Xanthines

41
Q
A

monobactams

42
Q
A

indole

43
Q
A

piperidine

44
Q
A

pyrrolidine

45
Q
A

azepane

-ane 7 membered saturated

46
Q
A

tetrohydrofuran

47
Q
A

1,4-thiazepine

48
Q

saturated 10-membered heterocycle

unsaturated

A
  • ecane
  • ecine
49
Q
A

thiepane

50
Q
A

1,3-dithietane

51
Q

saturated 9-membered heterocycle

unsaturated

A

-onane

-onine

52
Q
A

Thietane

53
Q
A

1,3-diazepane

54
Q
A

benzo[b][1,4]thiazepine

55
Q
A

imidazole

56
Q
A

pyridazine

57
Q

S>O>N

Order of Increasing logP = Lipophilicity (SOLUBILITY)

N>O>S

Order of Increasing POLARITY

A

logP trends

58
Q
A

isoquinoline

59
Q
A

1H-1,4-diazepine

60
Q
A

thiepine

61
Q

saturated 4-membered herterocycle

unsaturated

saturated w/ NITROGEN

A

-etane

-ete

-etidine

62
Q
A

benzothiophene

63
Q
A

carbapenams

64
Q

saturated 7-membered heterocycles

unsaturated

A

-epane

-epine

65
Q
A

Oxirane

66
Q
A

thiazole

1,3-thiazole

67
Q

pyrimidine

A

pyrimidine

68
Q

Ketone = 2

Ether = 2

Imine = 1

Oxazole = 1

A

H-Bond Acceptors

69
Q
A

Azetidine

-etidine for N 4 membered sat rings

70
Q
A

Oxetane

-etane 4 membered saturated ring

71
Q
A

quinoxaline

72
Q
A

guanine

73
Q
A

cephem

74
Q
A

pyrazine

75
Q
A

clavams

76
Q
A

L-proline

77
Q
A

benzoimidazole

78
Q
A

beta-lactam

79
Q

saturated 3-membered Heterocycle

unsaturated (double bonds)

saturated w/ NITROGEN (aza-)

A

-irane

-irane

-iridine

80
Q
A

1,2,4-triazole

81
Q

90%> likely that compounds with 2+ of these characteristics will have poor absorption properties

A

lipinski’s rule of 5

Poor oral absorption and/or distribution are more likely when:

82
Q
A

penem

83
Q
A

oxazole

1,3-oxazole

MedChem Midterm 2 (6 decks)

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