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MedChem Midterm 2 > Hetrocycles > Flashcards

Hetrocycles Flashcards

1
Q

thiophene

A
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2
Q

1H-1,4-diazepine

A
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3
Q

pyridazine

A
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4
Q

-etane

-ete

-etidine

A

saturated 4-membered herterocycle

unsaturated

saturated w/ NITROGEN

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5
Q

penem

A
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6
Q

monobactams

A
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7
Q

benzo[b][1,4]thiazepine

A
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8
Q

pyridine

-ine 6 membered unsaturated

A
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9
Q

imidazole

A
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10
Q

-ocane

-ocine

A

saturated 8-membered heterocycles

unsaturated

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11
Q

pyrrole

A
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12
Q

tetrazole

A
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13
Q

-irane

-irane

-iridine

A

saturated 3-membered Heterocycle

unsaturated (double bonds)

saturated w/ NITROGEN (aza-)

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14
Q

-olane

-ole

-olidine

A

saturated 5-membered heterocycles

unsaturated

saturated w/ NITROGEN

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15
Q

carbapenams

A
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16
Q

Oxetane

-etane 4 membered saturated ring

A
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17
Q

1,3-diazepane

A
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18
Q

1,2-diazepane

A
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19
Q

tetrahydrothiophene

A
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20
Q

Azetidine

-etidine for N 4 membered sat rings

A
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21
Q

thiepine

A
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22
Q

-inane

-ine

A

saturated 6-membered heterocycle

unsaturated (aromatic)

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23
Q

penams

A
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24
Q

furan

A
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25
Q

quinoline

A
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26
Q

tetrohydrofuran

A
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27
Q

benzoimidazole

A
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28
Q

oxapenams

A
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29
Q

1,3-dithietane

A
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30
Q

L-proline

A
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31
Q

Xanthines

A
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32
Q

benzothiazole

A
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33
Q

pyrrolidine

A
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34
Q

logP trends

A

S>O>N

logP = Lipophilicity (SOLUBILITY)

*Molecules w/ S are more soluble than with N

N>O>S

POLARITY, N is most POLAR

35
Q

Thietane

A
36
Q

Oxirane

A
37
Q

1,2,4-triazole

A
38
Q

H-Bond Acceptors

A

Ketone = 2

Ether = 2

Imine = 1

Oxazole = 1

39
Q
  • ecane
  • ecine
A

saturated 10-membered heterocycle

unsaturated

40
Q

quinazoline

A
41
Q

1,2,3-triazole

A
42
Q

penems

A
43
Q

cepham

A
44
Q

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

A
45
Q

morpholine

A
46
Q

guanine

A
47
Q

pKa’s of

Pyridine

Pyridazine

Pyrimidine

Pyrazine

A
48
Q

benzoxazole

A
49
Q

pyrimidine

A

pyrimidine

50
Q

indole

A
51
Q

H-Bond Donors

A

Alcohol = 1

Amide = 1

imidazole = 1

pyrrole = 1

1*(primary) amine = 2

52
Q

piperidine

A
53
Q

isoquinoline

A
54
Q

benzotriazole

A
55
Q

cephem

A
56
Q

Aziridine

-idine for Nitrogens (3 membered staturated)

A
57
Q

clavams

A
58
Q

cabapenems

A
59
Q

adenine

A
60
Q

azepane

-ane 7 membered saturated

A
61
Q

Thiirane

-irane for 3 membered rings (saturated)

A
62
Q

lipinski’s rule of 5

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

A

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

63
Q

Order of Reactivity

Beta Lactams

A
64
Q

isoxazole

1,2-oxazole

A
65
Q

pyrazine

A
66
Q

1,4-thiazepine

A
67
Q

penam

A
68
Q

purine

A
69
Q

cephems

A
70
Q

oxacephems

A
71
Q

thiazole

1,3-thiazole

A
72
Q

thiepane

A
73
Q

isothiazole

1,2-thiazole

A
74
Q

cinnoline

A
75
Q

quinoxaline

A
76
Q

carbacephems

A
77
Q

azepine

-ine 7 membered UNSATURATED

A
78
Q

oxazole

1,3-oxazole

A
79
Q

1,4-diazepane

A
80
Q

benzothiophene

A
81
Q

beta-lactam

A
82
Q

-onane

-onine

A

saturated 9-membered heterocycle

unsaturated

83
Q

-epane

-epine

A

saturated 7-membered heterocycles

unsaturated

MedChem Midterm 2 (6 decks)

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