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"Click" reaction in conjunction with diazeniumdiolate chemistry: developing high-load nitric oxide donors.

ABSTRACT: 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.

SUBMITTER: Oladeinde OA

PROVIDER: S-EPMC2945422 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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"Click" reaction in conjunction with diazeniumdiolate chemistry: developing high-load nitric oxide donors.

Oladeinde Oyebola A OA Hong Sam Y SY Holland Ryan J RJ Maciag Anna E AE Keefer Larry K LK Saavedra Joseph E JE Nandurdikar Rahul S RS

Organic letters 20101001 19

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 c ...[more]

PMID: 20812718

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