Bis basic-substituted polycyclic aromatic compounds. New class of antiviral agents. 2. Tilorone and related bis-basic ethers of fluorenone, fluorenol, and fluorene

Andrews, E. R.; Fleming, Robert W.; Grisar, J. M.; Kihm, J. C.; Wenstrup, David L.; Mayer, Gerald D.

doi:10.1021/jm00254a020

Cited by 62 publications

(24 citation statements)

References 3 publications

(4 reference statements)

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“…It was, however, a surprising finding that Aeranil containing a single dialkylamino-alkyl side chain was just as effective in vaccinia virus infection as tilorone bearing two such side chains. In the comprehensive structureactivity studies on several tricyclie aromatic series of compounds (tilorone congeners), the derivatives with one side chain instead of two were found slightly active or inactive by the Merrell group of investigators (2,20,18). No acridines were included in their studies.…”

Section: Discussionmentioning

confidence: 99%

Comparison of the activity of small molecular interferon inducers: Tilorone and acridine drugs

Gláz

Tálas

1975

Archives of Virology

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The antiviral activity and induction of interferon-like substance by mepacrine (quinacrine, Atabrine) and Acranil in mice, described previuosly, was studied in more detail and compared with tilorone. The serum substance induced by Acranil was characterized as mouse interferon. Acranil, given parenterally, proved to be as strong as tilorone regarding interferon stimulation, in spite of the presence of only one side chain in the Acrainl molecule. Mepacrine was found to be a wealer interferon inducer than either tilorone or Acranil. The mode of interferon induction by Acranil and tilorone (effect of metabolic inhibitors, hyporesponsiveness to repeated doses, correlation between acute toxicity and antiviral activity, failure of effectiveness in chicks and chicken embryo tissue culture) was found comparable. However, the body temperature reactions of mice to the drugs were different: a striking hypothermic effect of tilorone, a lower one of mepacrine and the absence of body temperature depression by Acranil was observed.

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Section: Discussionmentioning

confidence: 99%

Comparison of the activity of small molecular interferon inducers: Tilorone and acridine drugs

Gláz

Tálas

1975

Archives of Virology

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“…Tilorone hydrochloride (10) showed antiviral activity against the Semliki forest virus, a RNA virus of the arbovirus group, vesicular stomatitis virus, mengovirus, herpes simplex, DNA virus, the RNA myxoviruses, influenza B, influenza A/equine-1, and influenza A 2 virus. [12] Etiojervane is a testosterone analog and etiojervane related compound 11 ( Figure 1) has been synthesized from substituted fluorenone intermediates. [13]…”

Section: Fluorenone Derivatives As Antiviral Agentsmentioning

confidence: 99%

A Perspective on Synthesis and Applications of Fluorenones

et al. 2020

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Fluorenones are important constituents in material, medical and chemical sciences with potential applications in various domains. The key factors responsible for the diverse usage of fluorenones in material sciences are their intriguing and tunable photo, as well as physico‐chemical properties. Besides this, the presence of conjugated poly‐(en)ynes in the fluorenones makes them molecules of interest in material sciences. Fluorenones show various biological activities like antibiotics, anticancer, antiviral, and neuromodulatory, etc. Organic chemists are developing various protocols for the synthesis of fluorenones. Despite several protocols developed for their synthesis since 1931, there is no review covering their entire synthetic protocols. This review includes several classical and novel synthetic approaches for the synthesis of fluorenones. Furthermore, we delineated the mechanism by which they have been synthesized.

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“…As starting compound we used relatively accessible 2,7-dihydroxy-9H-fluoren-9-one (I) [7]. Its alkylation with monochloro derivatives of di-, tri-, and tetraethylene glycols (compounds IIaIIc) in DMF in the presence of potassium carbonate gave diols IIIa IIIc in 7880% yield (Scheme 1).…”

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confidence: 99%