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Novel protection-deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO.

ABSTRACT: Synthesis of previously inaccessible, potentially liver selective HNO donor V-IPA/NO ([iPrHN(3)-N(1)(O(1))=N(2)-O(2)-R], where R = vinyl) is reported here. A novel fluoride-labile TOM group at O-2 in conjunction with MOM protection at N-3 in IPA/NO is employed. The strategy developed is also extended to synthesis of other NO-releasing prodrugs and has applications in diversity-oriented synthesis of HNO- and NO-prodrugs.

SUBMITTER: Nandurdikar RS

PROVIDER: S-EPMC6959522 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Novel protection-deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO.

Nandurdikar Rahul S RS Keefer Larry K LK Saavedra Joseph E JE

Chemical communications (Cambridge, England) 20110510 23

Synthesis of previously inaccessible, potentially liver selective HNO donor V-IPA/NO ([iPrHN(3)-N(1)(O(1))=N(2)-O(2)-R], where R = vinyl) is reported here. A novel fluoride-labile TOM group at O-2 in conjunction with MOM protection at N-3 in IPA/NO is employed. The strategy developed is also extended to synthesis of other NO-releasing prodrugs and has applications in diversity-oriented synthesis of HNO- and NO-prodrugs. ...[more]

PMID: 21556407

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