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.
Publication types
-
Research Support, N.I.H., Intramural
MeSH terms
-
Circular Dichroism
-
Cyclization
-
HIV Reverse Transcriptase / antagonists & inhibitors*
-
HIV Reverse Transcriptase / metabolism
-
Molecular Structure
-
Reverse Transcriptase Inhibitors / chemical synthesis*
-
Reverse Transcriptase Inhibitors / chemistry
-
Reverse Transcriptase Inhibitors / pharmacology*
-
Structure-Activity Relationship
-
Thiophenes / chemical synthesis
-
Thiophenes / chemistry*
-
Thiophenes / pharmacology*
Substances
-
NSC-380292
-
Reverse Transcriptase Inhibitors
-
Thiophenes
-
benzothiophene
-
HIV Reverse Transcriptase