title: 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.
authors.affiliation: Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, MD 21702, USA. nandurdikarr@mail.nih.gov
authors.forename: Rahul S
authors.initials: RS
authors.lastname: Nandurdikar
authors.forename: Larry K
authors.initials: LK
authors.lastname: Keefer
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Saavedra
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry / Q000378:metabolism; D009569:Nitric Oxide / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry; D011355:Prodrugs / Q000138:chemical synthesis / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001391:Azo Compounds; D009589:Nitrogen Oxides; D011355:Prodrugs; D014753:Vinyl Compounds; C452539:diazeniumdiolate; D009569:Nitric Oxide; D003577:Cytochrome P-450 Enzyme System; C039900:nitroxyl