Hetrocycles Flashcards by Karlo Sison

Q

thiophene

A

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Q

1H-1,4-diazepine

A

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Q

pyridazine

A

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Q

-etane

-ete

-etidine

A

saturated 4-membered herterocycle

unsaturated

saturated w/ NITROGEN

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Q

penem

A

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Q

monobactams

A

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Q

benzo[b][1,4]thiazepine

A

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Q

pyridine

-ine 6 membered unsaturated

A

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Q

imidazole

A

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Q

-ocane

-ocine

A

saturated 8-membered heterocycles

unsaturated

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Q

pyrrole

A

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Q

tetrazole

A

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Q

-irane

-irane

-iridine

A

saturated 3-membered Heterocycle

unsaturated (double bonds)

saturated w/ NITROGEN (aza-)

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Q

-olane

-ole

-olidine

A

saturated 5-membered heterocycles

unsaturated

saturated w/ NITROGEN

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Q

carbapenams

A

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Q

Oxetane

-etane 4 membered saturated ring

A

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Q

1,3-diazepane

A

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Q

1,2-diazepane

A

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Q

tetrahydrothiophene

A

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Q

Azetidine

-etidine for N 4 membered sat rings

A

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Q

thiepine

A

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Q

-inane

-ine

A

saturated 6-membered heterocycle

unsaturated (aromatic)

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Q

penams

A

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Q

furan

A

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Q

quinoline

A

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Q

tetrohydrofuran

A

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Q

benzoimidazole

A

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Q

oxapenams

A

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Q

1,3-dithietane

A

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Q

L-proline

A

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Q

Xanthines

A

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Q

benzothiazole

A

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Q

pyrrolidine

A

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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

Q

Thietane

A

Q

Oxirane

A

Q

1,2,4-triazole

A

Q

H-Bond Acceptors

A

Ketone = 2

Ether = 2

Imine = 1

Oxazole = 1

Q

ecane
ecine

A

saturated 10-membered heterocycle

unsaturated

Q

quinazoline

A

Q

1,2,3-triazole

A

Q

penems

A

Q

cepham

A

Q

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

A

Q

morpholine

A

Q

guanine

A

Q

pKa’s of

Pyridine

Pyridazine

Pyrimidine

Pyrazine

A

Q

benzoxazole

A

Q

pyrimidine

A

pyrimidine

Q

indole

A

Q

H-Bond Donors

A

Alcohol = 1

Amide = 1

imidazole = 1

pyrrole = 1

1*(primary) amine = 2

Q

piperidine

A

Q

isoquinoline

A

Q

benzotriazole

A

Q

cephem

A

Q

Aziridine

-idine for Nitrogens (3 membered staturated)

A

Q

clavams

A

Q

cabapenems

A

Q

adenine

A

Q

azepane

-ane 7 membered saturated

A

Q

Thiirane

-irane for 3 membered rings (saturated)

A

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

Q

Order of Reactivity

Beta Lactams

A

Q

isoxazole

1,2-oxazole

A

Q

pyrazine

A

Q

1,4-thiazepine

A

Q

penam

A

Q

purine

A

Q

cephems

A

Q

oxacephems

A

Q

thiazole

1,3-thiazole

A

Q

thiepane

A

Q

isothiazole

1,2-thiazole

A

Q

cinnoline

A

Q

quinoxaline

A

Q

carbacephems

A

Q

azepine

-ine 7 membered UNSATURATED

A

Q

oxazole

1,3-oxazole

A

Q

1,4-diazepane

A

Q

benzothiophene

A

Q

beta-lactam

A

Q

-onane

-onine

A

saturated 9-membered heterocycle

unsaturated

Q

-epane

-epine

A

saturated 7-membered heterocycles

unsaturated