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Med Chem Final > Structures > Flashcards

Structures Flashcards

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1
Q

R-CH2OH

A

primary alcohol

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1
Q

R-COOH

A

Carboxylic acid

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2
Q

RCHO

A

aldehyde

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3
Q

ADH

A

alcohol dehydrogenase

catalyzes conversion of primary alcohol to aldehyde AND secondary alcohol to ketone

bulk in cytosol

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4
Q

is further oxidation of ketone possible

A

NO - dont have hydrogen

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5
Q

ALDH

A

aldehyde dehydrogenase

catalyzes conversion of aldehyde to corresponding carboxylic acid (irreversible)

bulk of ALDH is in mitochondria

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6
Q

CH2O

A

formaldehyde

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7
Q

CH3CHO

A

acetaldehyde

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8
Q

benzene ring with a + charge N connected to - charge O

A

N-oxide

formed from the oxidation of pyridine and other tertiary amines

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9
Q

pyridine is a ___ ___

A

tertiary amine

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10
Q

R-C(=O)-NR’R”

A

amide (carboxamide)

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11
Q

what is a dialkyl amide

A

amide with 2 alkyl groups bonded to the N

SLOW reaction
if 2 alpha carbons, either one can come off

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12
Q

Ether

A

R-O-R’

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13
Q

thioether

A

R-S-R’

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14
Q

what reaction produces a hemiacetal intermediate

A

O-dealkylation

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15
Q

RR’COR

A

HEMI ACETAL

carbon connected to 1 ether oxygen + 3 other substituents

VERY UNSTABLE

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16
Q

R-S-R what reaction does it undergo

A

sulfoxidation
(if 1 R group is methyl it’s a different story)

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17
Q

sulfide

A

R-S-R (also thioether)

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18
Q

sulfoxide

A

S=O (2 R groups on S)

19
Q

sulfone

A

O=S=O (2 R groups on S

20
Q

hemithioacetal

A

carbon connected to Sulfur that’s part of a thioether bond, and OH, plus 2 other substituents

21
Q

carbinolamine

A

metabolically unstable intermediate formed in O-deamination and N-dealkylation

carbon with an amine and hydroxyl group (+2 R’s)

22
Q

cyano group

A

C triple bond N

23
Q

acetonitrile

A

CH3-C triple bond N

1 of only cyano groups allowed in drug molecules because it is hydrophilic enough to be readily excreted

24
Q

“ketene”

A

=C=
formed in the oxidation of carbon-carbon triple bonds

reacts with h2o to produce corresponding carboxylic acid

25
Q

aniline

A

benzene ring with NH2 as the only substituent

likely to undergo N-hydroxylation

26
Q

Nitrenium ion

A

AR-N+-H

produced in N-hydroxylation of AR-NH2 if the aromatic ring is 2 or more fused rings.
there is enough stability for nitrenium ion to be there

POTENT CARCINOGEN

27
Q

nitroso

A

R-N=O

produced in the reduction of aromatic nitro compounds (from nitro radical)

this can only be done in the GI tract

28
Q

hydroxylamine

A

amineattached to hydroxyl

produced from the reduction of nitroso (can only be done by the microorganisms in the GI tract)

29
Q

nitrate

A

NO3-

NO DIRECT HYDROLYSIS. must be converted to nitrite

30
Q

nitrite

A

NO2-
O=N-O-

31
Q

hydrazide group

A

N-N

32
Q

name the amides that can be hydrolyzed

A

open chain
cyclic
hydrazides
urea type

33
Q

which open chain amides can be hydrolyzed?

A

primary and secondary amides

34
Q

which cyclic amides can be hydrolyzed?

A

imides and lactams

35
Q

give an example of an imide and a lactam
what reaction can they undergo?

A

lactam - penicillin
imide - phthalidone

they are cyclic amides that undergo HYDROLYSIS

36
Q

Nam a hydrazide that undergoes hydrolysis and explain the significance

A

isoniazid undergoes hydrolysis to produce a metabolite that is TOXIC to the liver

further oxidized to carbocation/radical species

37
Q

where is a thiourea clipped when it undergoes hydrolysis? name a thiourea

A

chloropropamide

clipped between NH and carbonyl

38
Q

which has more predictable hydrolysis - open chain urea or cyclic urea?

A

open chain is more predictable

39
Q

name 2 cyclic ureas

A

barbiturates - STABLE TO HYDROLYSIS
5-phenylhydantoin

40
Q

explain how cyclic ureas undergo less predictable hydrolysis than open chain

A

5-phenylhydantoin is a cyclic urea that undergoes hydrolysis

the barbiturates are cyclic ureas that do NOT undergo hydrolysis - stable to hydrolysis

41
Q

what is cyclamate

A

was almost introduced as a substitute for table sugar, but produces a carcinogen upon hydrolysis by gut bacterial enzymes

42
Q

carbamates undergo hydrolysis to produce….

A

alcohol, carbon dioxide, and amine

43
Q

acrolein

A

michael acceptor generated from the metabolism (oxidation) of cyclophosphamide

44
Q
A

Med Chem Final (11 decks)

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