Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. 8. Bis-basic derivatives of carbazole, dibenzofuran, and dibenzothiophene.
A series of bisalkamine esters, bis-basic ethers, and bis-basic ketones of carbazole, N-ethylcarbazole, dibenzofuran, and dibenzothiophene was synthesized and evaluated for antiviral activity. The series also included two bis-basic alkanes of N-ethylcarbazole and one bis-basic carboxamide of dibenzofuran. Structure-activity relationships indicated that within the carbazole and N-ethylcarbazole series the bisalkamine esters gave the most active derivatives while the bis-basic ketone derivatives of dibenzofuran and dibenzothiophene afforded the more potent compounds within the respective series. The [6,5,6]heterocyclic nuclei were compared with the [6,5,6] aromatic nuclei (fluroene and fluoren-9-one) including tilorone with respect to antiviral activity against encephalomyocarditis (EMC) virus. Maximum activity was associated with the bis-basic ketone side chain and fluoren-9-one nucleus.
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D002227:Carbazoles / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D004686:Encephalomyocarditis virus; D004769:Enterovirus Infections / Q000188:drug therapy; D006561:Herpes Simplex / Q000188:drug therapy; D008297:Male; D008722:Methods; D051379:Mice; D008819:Mice, Nude; D018139:Simplexvirus / Q000187:drug effects; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use
D000998:Antiviral Agents; D001572:Benzofurans; D002227:Carbazoles; D013876:Thiophenes