title: "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.
authors.affiliation: Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland 21702, USA.
authors.forename: Oyebola A
authors.initials: OA
authors.lastname: Oladeinde
authors.forename: Sam Y
authors.initials: SY
authors.lastname: Hong
authors.forename: Ryan J
authors.initials: RJ
authors.lastname: Holland
authors.forename: Anna E
authors.initials: AE
authors.lastname: Maciag
authors.forename: Larry K
authors.initials: LK
authors.lastname: Keefer
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Saavedra
authors.forename: Rahul S
authors.initials: RS
authors.lastname: Nandurdikar
mesh_terms: D001386:Azides / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D020030:Nitric Oxide Donors / Q000737:chemistry*
chemical_list: D001386:Azides; D001391:Azo Compounds; D020030:Nitric Oxide Donors; C452539:diazeniumdiolate
references.citation: Br J Pharmacol. 2007 Jun;151(3):305-21
references.pmid: 17401442
references.citation: Drug Discov Today. 2003 Dec 15;8(24):1128-37
references.pmid: 14678739
references.citation: J Med Chem. 2008 Jul 10;51(13):3961-70
references.pmid: 18533711
references.citation: Angew Chem Int Ed Engl. 1999 Jul 12;38(13-14):1870-1880
references.pmid: 34182659
references.citation: Angew Chem Int Ed Engl. 2002 Jul 15;41(14):2596-9
references.pmid: 12203546
references.citation: Angew Chem Int Ed Engl. 2007;46(20):3649-51
references.pmid: 17410632
references.citation: Pharmacol Rev. 1991 Jun;43(2):109-42
references.pmid: 1852778
references.citation: Org Lett. 2010 Jan 1;12(1):56-9
references.pmid: 19954198
references.citation: ChemMedChem. 2008 May;3(5):715-23
references.pmid: 18214878
references.citation: Chem Rev. 2002 Apr;102(4):1135-54
references.pmid: 11942789
references.citation: J Org Chem. 2002 May 3;67(9):3057-64
references.pmid: 11975567
references.citation: Angew Chem Int Ed Engl. 2007;46(7):1018-25
references.pmid: 17211903
references.citation: Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2004-2021
references.pmid: 11433435
references.citation: Chem Rev. 2008 Aug;108(8):2952-3015
references.pmid: 18698735
references.citation: Expert Opin Investig Drugs. 2002 May;11(5):587-601
references.pmid: 11996642
references.citation: Chem Res Toxicol. 2002 Mar;15(3):269-99
references.pmid: 11896674
references.citation: Angew Chem Int Ed Engl. 2005 Apr 8;44(15):2210-5
references.pmid: 15693051
references.citation: Anticancer Agents Med Chem. 2009 Sep;9(7):798-803
references.pmid: 19538173
references.citation: J Pharmacol Exp Ther. 2002 Jan;300(1):18-25
references.pmid: 11752092
references.citation: Chem Rev. 2002 Apr;102(4):1091-134
references.pmid: 11942788
references.citation: Bioorg Med Chem Lett. 2009 May 15;19(10):2760-2
references.pmid: 19364650
references.citation: Angew Chem Int Ed Engl. 1999 Jul 12;38(13-14):1882-1892
references.pmid: 34182699