title: The synthesis of novel heteroaryl-fused 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indoles, 4-oxo-2,3-dihydro-1H-[1,4]diazepino[1,7-a]indoles and 1,2,4,5-tetrahydro-[1,4]oxazepino[4,5-a]indoles. Effective inhibitors of HCV NS5B polymerase.
abstract: Three synthetic approaches have been developed that allow efficient access to novel heteroaryl fused indole ring systems, including: 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indoles, 4-oxo-2,3-dihydro-1H-[1,4]diazepino[1,7-a]indoles and 1,2,4,5-tetrahydro-[1,4]oxazepino[4,5-a]indoles. Each strategy is fully exemplified and the relative merits and limitations of the approaches are discussed. The hepatitis C virus (HCV) non-structural 5B (NS5B) polymerase inhibitory activities of select examples from each molecular class are briefly presented.
authors.affiliation: Discovery Chemistry, Research and Development, Bristol-Myers Squibb Co., 5 Research Parkway, Wallingford, CT 06492, USA. min.ding@bms.com
authors.forename: Min
authors.initials: M
authors.lastname: Ding
authors.forename: Feng
authors.initials: F
authors.lastname: He
authors.forename: Michael A
authors.initials: MA
authors.lastname: Poss
authors.forename: Karen L
authors.initials: KL
authors.lastname: Rigat
authors.forename: Ying-Kai
authors.initials: YK
authors.lastname: Wang
authors.forename: Susan B
authors.initials: SB
authors.lastname: Roberts
authors.forename: Dike
authors.initials: D
authors.lastname: Qiu
authors.forename: Robert A
authors.initials: RA
authors.lastname: Fridell
authors.forename: Min
authors.initials: M
authors.lastname: Gao
authors.forename: Robert G
authors.initials: RG
authors.lastname: Gentles
mesh_terms: D060326:Chemistry Techniques, Synthetic; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D017361:Viral Nonstructural Proteins / Q000037:antagonists & inhibitors*; D012324:RNA-Dependent RNA Polymerase
chemical_list: D007211:Indoles; D017361:Viral Nonstructural Proteins; C087036:NS-5 protein, hepatitis C virus; D012324:RNA-Dependent RNA Polymerase