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Designs and syntheses of oxathiin carboxanilide analogues and their antiviral activities

Authors
Hahn, HCRhee, HKLee, CKWhang, KJ
Issue Date
Aug-2000
Publisher
PHARMACEUTICAL SOCIETY KOREA
Keywords
heterocyclic carboxanilide; oxathiins; thiazines; dithiins; thiocarboxanilides; antiviral activities
Citation
ARCHIVES OF PHARMACAL RESEARCH, v.23, no.4, pp.315 - 323
Journal Title
ARCHIVES OF PHARMACAL RESEARCH
Volume
23
Number
4
Start Page
315
End Page
323
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/16748
DOI
10.1007/BF02975440
ISSN
0253-6269
Abstract
Syntheses of new analogues of oxathiin carboxanilide (UC84) and their antiviral activities were described. The heterocyclic carboxylic acids including oxathiins (4), thiazines (9) and dithiins (13) in which the methyl was replaced either by lipophilic trifluoromethyl- or bulky phenyl-group were synthesized starting from beta-keto esters (5). Reaction of 4, 9 and 13 with thionyl chloride followed by treatment of the substituted aniline 22 gave the corresponding carboxanilides (24a similar to 24f). The carboxanilides were subjected to Laweson's reagent the corresponding thiocarboxanilides (24g similar to 24k). The antiviral activities of the synthesized compounds against human immunodeficiency virus type 1 (HIV-1), poliovirus type 1 (PV-1), coxsackie B virus type 3 (CoxB-3), vesicular stomatitis virus (VSV) and herpes simplex virus type 1 (HSV-1) were presented. The antiviral activity against HIV-1 of dithiin carboxanilide (24e) was similar with that of UC84 (24a). The corresponding thiocarboxanilides (24g similar to 24k) showed higher inhibitory activity against HIV-1 than the carboxanilides (24a, 24b, 24d, 24e). The compounds in which ether the lipophilic trifluoromethyl substituents (24d, 24f, 24i, 24k) or bulky phenyl substituent is present in the heterocyclic compounds showed lower inhibitory activity than that of the methyl substituents is present in the compounds against the HIV-1. But the trifluoromethylated dithiin (24f) showed higher inhibitory activity against PV-1 and CoxB-3 virus than commercial antiviral agents, ribavirin (RV).
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