Chemistry Reference
In-Depth Information
O
O
O
O
O
O
N
H
2
N
N
N
N
N
N
n
-
C
7
H
15
O
−
O
−
N
N
H
O
2
C
H
O
O
−
N
O
−
N
H
H
Alanosine
Dopastin
Fragin
O
O
O
O
O
H
H
O
A
c
O
H
O
2
C
N
N
N
(
C
H
2
)
8
N
O
−
N
n
-
C
1
5
H
3
1
O
−
N
R
O
−
O
−
N
N
N
H
2
C
H
2
O
H
Homoalanosine
Nitrosostromelin
R = i -PrCH
2
(CH
2
)
11
−
; i -PrCH
2
(CH
2
)
9
−
; or H
3
C(CH
2
)
13
−
Nitrosoxacins
Poecillanosine
Figure4.9
Naturallyoccurringdiazeniumdiolatesandtheirbiochemistry.
196 - 209
Table4.7
Knownbiochemistryofnaturaldiazeniumdiolates
Diazeniumdiolate
Source
Recognized
Pharmacology
Known inhibitor of
Ref.
Alanosine
StreptomycesA
Cancer Chemotherapy,
(Phase II) Antibiotic,
Antiviral
Adenylsuccinate synthase
[197, 199-201]
Dopastin
Streptomyces?
Dopamine
β
−
hydroxylase
[196, 198-200]
Fragin
Pseudomonas
Herbicide
[202-206]
Homoalanosine
Herbicide
[199]
Nitrosoxacins
Streptomyces?
Antibiotic
5-lipoxygenase
[207]
Nitrosostromelin
Streptomyces
Stromelysin
[207]
Poecillanosine
Marinesponges
[208, 209]
of considerable theoretical and practical activity, with much of this interest stemming from the use of
dialkylaminediazeniumdiolates as nitric oxide donors in biomedical applications.
O
−
N
(4.22)
2NO
+
HSO
3
−
N
−
H
+
O
−
O
3
S
Under basic conditions secondary amines react rapidly with nitric oxide to give diazeniumdiolates,
which are readily isolated as their dialkylammonium salts (Equation 4.23).
175
The retro reaction in neutral
conditions returns nitric oxide,
176
with their rate of nitric oxide release being dependent upon the nitrogen
substituents.
177
With the exception of three cyclic cases (Figure 4.10),
178 - 180
the diazeniumdiolates which
Search WWH ::
Custom Search