Pyran-chromenone compounds, their synthesis and anti-HIV activity
AssigneeThe University of Tennessee Research Corporation
InventorDavid Baker
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Abstract
The invention relates to pyran-chromenone compounds, their synthesis and anti-HIV activity. Methods of synthesis are disclosed; the compounds have activity against reverse transcriptase. Biological compositions containing the compounds and method of treating patients are also disclosed.
Claims33
An optically active pyran-chromenone compound of either one of the A or B series of the formula ##STR2## in which R.sup.1 is straight or branched alkyl of not more than 6 carbon atoms, cycloalkyl of not more than 8 carbon atoms, allyl, alkenyl wherein tbe alkyl has not more than 6 carbon atoms, alkaryl wherein the aryl has not more 6 carbon atoms, R.sup.2 is hydrogen, straight or branched alkyl, cycloalkyl or aryl wherein the alkyl or aryl is of not more than 6 carbon atoms and R.sup.3 is hydroxyl or keto.
The fused pyran-chromenone of the structure ##STR5## wherein R.sup.1 is lower alkyl, allyl, or propargyl R.sup.2 is 1-propyl and OTBDMS is OSiMe.sub.2 tert-butyldimethylsilane or tert-butyldimethylsilane.
The homoallylic compounds of the structure ##STR6## wherein R.sup.1 is lower alkyl, allyl, or propargyl, R.sup.2 is 1-propyl and.
The 8-methyl-10-pyranones of the structure ##STR7## wherein R.sup.1 is isopropyl, allyl, or propargyl and R.sup.2 is 1-propyl.
The trans-8,9-dimethylpyranone compounds of the structure ##STR8## wherein R.sup.1 is isopropyl, allyl, or propargyl and R.sup.2 is 1-propyl.
A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and in a nontoxic effective amount, a pyran-chromenone of the formula ##STR9## or a pharmaceutically acceptable salt thereof, in which R.sup.1 is straight or branched alkyl of not more than 6 carbon atoms, cycloalkyl of not more than 8 carbon atoms, allyl, alkenyl wherein the alkyl has not more than 6 carbon atoms, alkaryl wherein the aryl has not more than 6 carbon atoms, R.sup.2 is hydrogen, straight or branched alkyl, cycloalkyl or aryl wherein the alkyl or aryl is of not more than 6 carbon atoms and R.sup.3 is hydroxyl or keto.
A method for treating or preventing a viral infection, which method comprises administering to a human an antiviral, nontoxic amount of at least one pyran-chromenone of the formula ##STR14## in which R.sup.1 is straight or branched alkyl of not more than 6 carbon atoms, cycloalkyl of not more than 8 carbon atoms, allyl, alkenyl wherein the alkyl has not more than 6 carbon atoms, alkaryl wherein the aryl has not more than 6 carbon atoms, R.sup.2 is hydrogen, straight or branched alkyl, cycloalkyl or aryl wherein the alkyl or aryl is of not more than 6 carbon atoms and R.sup.3 is hydroxyl or keto.
Dependencies are inferred from the claim text.