Structures Flashcards
R-CH2OH
primary alcohol
R-COOH
Carboxylic acid
RCHO
aldehyde
ADH
alcohol dehydrogenase
catalyzes conversion of primary alcohol to aldehyde AND secondary alcohol to ketone
bulk in cytosol
is further oxidation of ketone possible
NO - dont have hydrogen
ALDH
aldehyde dehydrogenase
catalyzes conversion of aldehyde to corresponding carboxylic acid (irreversible)
bulk of ALDH is in mitochondria
CH2O
formaldehyde
CH3CHO
acetaldehyde
benzene ring with a + charge N connected to - charge O
N-oxide
formed from the oxidation of pyridine and other tertiary amines
pyridine is a ___ ___
tertiary amine
R-C(=O)-NR’R”
amide (carboxamide)
what is a dialkyl amide
amide with 2 alkyl groups bonded to the N
SLOW reaction
if 2 alpha carbons, either one can come off
Ether
R-O-R’
thioether
R-S-R’
what reaction produces a hemiacetal intermediate
O-dealkylation
RR’COR
HEMI ACETAL
carbon connected to 1 ether oxygen + 3 other substituents
VERY UNSTABLE
R-S-R what reaction does it undergo
sulfoxidation
(if 1 R group is methyl it’s a different story)
sulfide
R-S-R (also thioether)
sulfoxide
S=O (2 R groups on S)
sulfone
O=S=O (2 R groups on S
hemithioacetal
carbon connected to Sulfur that’s part of a thioether bond, and OH, plus 2 other substituents
carbinolamine
metabolically unstable intermediate formed in O-deamination and N-dealkylation
carbon with an amine and hydroxyl group (+2 R’s)
cyano group
C triple bond N
acetonitrile
CH3-C triple bond N
1 of only cyano groups allowed in drug molecules because it is hydrophilic enough to be readily excreted
“ketene”
=C=
formed in the oxidation of carbon-carbon triple bonds
reacts with h2o to produce corresponding carboxylic acid
aniline
benzene ring with NH2 as the only substituent
likely to undergo N-hydroxylation
Nitrenium ion
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
nitroso
R-N=O
produced in the reduction of aromatic nitro compounds (from nitro radical)
this can only be done in the GI tract
hydroxylamine
amineattached to hydroxyl
produced from the reduction of nitroso (can only be done by the microorganisms in the GI tract)
nitrate
NO3-
NO DIRECT HYDROLYSIS. must be converted to nitrite
nitrite
NO2-
O=N-O-
hydrazide group
N-N
name the amides that can be hydrolyzed
open chain
cyclic
hydrazides
urea type
which open chain amides can be hydrolyzed?
primary and secondary amides
which cyclic amides can be hydrolyzed?
imides and lactams
give an example of an imide and a lactam
what reaction can they undergo?
lactam - penicillin
imide - phthalidone
they are cyclic amides that undergo HYDROLYSIS
Nam a hydrazide that undergoes hydrolysis and explain the significance
isoniazid undergoes hydrolysis to produce a metabolite that is TOXIC to the liver
further oxidized to carbocation/radical species
where is a thiourea clipped when it undergoes hydrolysis? name a thiourea
chloropropamide
clipped between NH and carbonyl
which has more predictable hydrolysis - open chain urea or cyclic urea?
open chain is more predictable
name 2 cyclic ureas
barbiturates - STABLE TO HYDROLYSIS
5-phenylhydantoin
explain how cyclic ureas undergo less predictable hydrolysis than open chain
5-phenylhydantoin is a cyclic urea that undergoes hydrolysis
the barbiturates are cyclic ureas that do NOT undergo hydrolysis - stable to hydrolysis
what is cyclamate
was almost introduced as a substitute for table sugar, but produces a carcinogen upon hydrolysis by gut bacterial enzymes
carbamates undergo hydrolysis to produce….
alcohol, carbon dioxide, and amine
acrolein
michael acceptor generated from the metabolism (oxidation) of cyclophosphamide
