title: Nitrosopurines en route to potently cytotoxic asmarines.
abstract: A nitrosopurine ene reaction easily assembles the asmarine pharmacophore and transmits remote stereochemistry to the diazepine-purine hetereocycle. This reaction generates potent cytotoxins which exceed the potency of asmarine A (1.2 μM IC50) and supersede the metabolites as useful leads for biological discovery.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, CA 92037 (USA).
authors.forename: Kanny K
authors.initials: KK
authors.lastname: Wan
authors.forename: Kotaro
authors.initials: K
authors.lastname: Iwasaki
authors.forename: Jeffrey C
authors.initials: JC
authors.lastname: Umotoy
authors.forename: Dennis W
authors.initials: DW
authors.lastname: Wolan
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Shenvi
mesh_terms: D001381:Azepines / Q000737:chemistry; D002470:Cell Survival / Q000187:drug effects; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D019073:HT29 Cells; D006801:Humans; D011687:Purines / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D001381:Azepines; D003603:Cytotoxins; D004224:Diterpenes; D011687:Purines
keywords: alkaloids; ene reaction; natural products; structure-activity relationships; terpenoids