"Click" reaction in conjunction with diazeniumdiolate chemistry: developing high-load nitric oxide donors.
The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO(4)/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.
Oladeinde
Oyebola A
OA
Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland 21702, USA.
Hong
Sam Y
SY
Holland
Ryan J
RJ
Maciag
Anna E
AE
Keefer
Larry K
LK
Saavedra
Joseph E
JE
Nandurdikar
Rahul S
RS
D001386:Azides / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D020030:Nitric Oxide Donors / Q000737:chemistry*
D001386:Azides; D001391:Azo Compounds; D020030:Nitric Oxide Donors; C452539:diazeniumdiolate
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