Synthesis of 5,8-dimethoxy-3-hydroxy-4-quinolone, a reported inhibitor of HIV RT, and evidence the original proposed structure was incorrect.
An unambiguous total synthesis of the title compound, a semi-synthetic derivative reported to be a non-nucleoside reverse transcriptase inhibitor, was conducted in four steps from 2,5-dimethoxyaniline. The synthetic material differed from that reported in the literature, both in its physical properties and 1H NMR spectrum. Biological evaluation indicated that synthetic 2 was inactive against HIV-1 RT, suggesting that the previous structural assignment of the semi-synthetic derivative was incorrect.
Zembower
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MediChem Research, Inc., Lemont, IL 60439, USA.
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D054303:HIV Reverse Transcriptase / Q000187:drug effects; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C118934:5,8-dimethoxy-3-hydroxy-4-quinolone; D006912:Hydroxyquinolines; D015363:Quinolones; D018894:Reverse Transcriptase Inhibitors; D054303:HIV Reverse Transcriptase