37972-07-9Relevant academic research and scientific papers
Antiviral compositions containing bis-basic ketones of xanthene and xanthen-9-one
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, (2008/06/13)
Novel bis-basic ketones of xanthene and xanthen-9-one have antiviral activity when administered orally and parenterally. The compounds are represented by the following formula: SPC1 Wherein Z is oxygen or H2 ; each A is a straight or branched alkylene chain having from 1 to about 6 carbon atoms; and each Y is A. the group EQU1 wherein R1 and R2 are individually hydrogen, lower alkyl having from 1 to about 6 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, alkenyl of from 3 to 6 carbon atoms and having the vinyl unsaturation in other than the 1-position of the alkenyl group; or B. the group EQU2 WHEREIN N IS A WHOLE INTEGER FROM 4 TO 6, AND R3 is hydrogen, lower alkyl of from 1 to about 4 carbon atoms and can be linked to any one of the carbon atoms of the heterocyclic group; or C. the group EQU3 wherein X is oxygen or NR4, and R4 is hydrogen or lower alkyl of from 1 to about 4 carbon atoms; Or a pharmaceutically acceptable acid addition salt thereof. These compounds can be prepared by several different methods.
Bis basic substituted polycyclic aromatic compounds. A new class of antiviral agents. 7. Bisalkamine esters, 3,6 bis basic ethers and 2,7 bis(aminoacyl)xanthen 9 ones
Carr,Grunwell,Sill
, p. 1142 - 1148 (2007/10/07)
3,6 Bis[2(dimethylamino)ethoxy] 9H xanthen 9 one dihydrochloride (4, RMI 0874DA) and 1,1' (9H xanthene 2,7 diyl)bis[2 (dimethylamino)ethanone] dihydrochloride (16, RMI 11513DA) were found to prolong survival of mice infected with lethal challenges of encephalomyocarditis (EMC) virus. They were effective by oral as well as subcutaneous administration and showed broad spectrum antiviral activity. They were selected for preclinical evaluation from the five series of compounds named in the title that were synthesized in analogy to tilorone and related fluorenone derivatives, described earlier. In addition to 4 and 16, compounds 11, 12, 17, and 18 showed high antiviral activity on oral as well as subcutaneous administration. High antiviral activity on subcutaneous administration was found in the bisalkamine esters 1, 2, and 14, the bis(aminoacyl)xanthenes 23 and 26, the bis(aminoalkylene)xanthene 31, the bis(aminoacyl)thioxanthenes 34-40, and the bis basic ethers of 9 benzylidenexanthenes 41 and 42. Structure activity relationships showed a decrease of oral activity with increased length of side chains and increased molecular weight of dialkylamino substituents of 3,6 bis basic ethers of xanthen 9 one and of 2,7 bis(aminoacyl) xanthenes and xanthen 9 ones. At least one carbonyl or alkenyl function in conjugation to the xanthene nucleus either at the 9 position of the nucleus or in the side chains is required for high antiviral activity.
