title: New HIV-1 reverse transcriptase inhibitors based on a tricyclic benzothiophene scaffold: synthesis, resolution, and inhibitory activity.
abstract: We synthesized, separated into enantiomers, and tested for the HIV-1 reverse transcriptase inhibitory activity a group of analogs of dimethyl-1-(1-piperidynyl)cyclobuta[b][1]benzothiophene-2,2a(7bH)-dicarboxylate (NSC-380292). Absolute configurations of the enantiomers were determined based on absolute X-ray structures and analysis of CD spectra. Within pairs of enantiomers the (R,R)-enantiomer was always much more potent HIV-1 reverse transcriptase inhibitor.
authors.affiliation: Laboratory of Medicinal Chemistry, CCR, NCI-Frederick, NIH, Frederick, MD 21702, USA.
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Krajewski
authors.forename: Yijun
authors.initials: Y
authors.lastname: Zhang
authors.forename: Damon
authors.initials: D
authors.lastname: Parrish
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Deschamps
authors.forename: Peter P
authors.initials: PP
authors.lastname: Roller
authors.forename: Vinay K
authors.initials: VK
authors.lastname: Pathak
mesh_terms: D002942:Circular Dichroism; D003500:Cyclization; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015394:Molecular Structure; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: C512160:NSC-380292; D018894:Reverse Transcriptase Inhibitors; D013876:Thiophenes; C088015:benzothiophene; D054303:HIV Reverse Transcriptase