title: Synthesis of Naamidine A and Selective Access to N(2)-Acyl-2-aminoimidazole Analogues.
abstract: A short and scalable synthesis of naamidine A, a marine alkaloid with a selective ability to inhibit epidermal growth factor receptor (EGFR)-dependent cellular proliferation, has been achieved. A key achievement in this synthesis was the development of a regioselective hydroamination of a monoprotected propargylguanidine to deliver N(3)-protected cyclic ene-guanidines. This permits the extension of this methodology to prepare N(2)-acyl analogues in a fashion that obviates the troublesome acylation of the free 2-aminoimidazoles, which typically yields mixtures of N(2)- and N(2),N(2)-diacylated products.
authors.affiliation: Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
authors.forename: Joseph B
authors.initials: JB
authors.lastname: Gibbons
authors.affiliation: Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
authors.forename: Justin M
authors.initials: JM
authors.lastname: Salvant
authors.affiliation: Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
authors.forename: Rachel M
authors.initials: RM
authors.lastname: Vaden
authors.affiliation: Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
authors.forename: Ki-Hyeok
authors.initials: KH
authors.lastname: Kwon
authors.affiliation: Immunobiology and Cancer Program, Oklahoma Medical Research Foundation , 825 Northeast 13th Street, Oklahoma City, Oklahoma 73104, United States.
authors.forename: Bryan E
authors.initials: BE
authors.lastname: Welm
authors.affiliation: Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
authors.forename: Ryan E
authors.initials: RE
authors.lastname: Looper
mesh_terms: D000215:Acylation; D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D000586:Amination; D000818:Animals; D066246:ErbB Receptors / Q000037:antagonists & inhibitors* / Q000737:chemistry* / Q000378:metabolism; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000470:Alkaloids; D006146:Guanidines; D007093:Imidazoles; C114816:naamidine A; C014973:2-aminoimidazole; D066246:ErbB Receptors