• Archives of Pharmacal Research
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• v.23 no.4
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• pp.315-323
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• 2000

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 phenylgroup 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~24f). The carboxanilides were subjected to Laweson's reagent the corresponding thiocarboxanilides (24g~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~24k) showed higher inhibitory activity against HIV-1 than the carboxanilides (24a, 24b, 24d, 24e). The compounds in which ether the lipophilic trifluorormethyl 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).

• Biomolecules & Therapeutics
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• v.11 no.1
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• pp.8-32
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• 2003

Garlic(Allium sativum L.) is one of the oldest cultivated plants and has been used throughout the world as food supplement and folk medicine for thousands of years. In modem times a number of garlic derived products are introduced on the market as health food supplement in ever growing scale. In 1844 German chemist Wertheim investigated the garlic first time chemically and thereafter many kinds of organosulfur compounds were isolated and their biological activities were elucidated scientifically. The main biological activities are antibacterial, antifungal, antithrombotic, cholesterol-lowering, antineoplastic and hepatoprotective activities. Chemical works as well as therapeutic and preventive effects of garlic are reviewed.

• Korean journal of food and cookery science
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• v.11 no.2
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• pp.133-139
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• 1995

Solvent extract of homogenates of fresh garlic or pickled garlic was subjected to GC-MS analysis, which showed 30 volatile sulfur compounds for fresh garlic and 20 compounds for processed one. Maior sulfur compounds from fresh garlic extract were identified to be 3-vinyl-[4H]-1,2-dithiin, diallyl disulfide,3,4-dimethylthiophene and methyl allyl sulfide. Meanwhile, the number of volatile compounds from pickled garlic decreased gradually during storage. Diallyl disulfide, methyl allyl trisulfide and diallyl trisulfide were major volatile sulfur compounds from pickled garlic stored for 50 days. It is appeared that the amount of trisulfides in pickled garlic increased gradually during storage, in contrast to the amount of dithiins and monosulfides in pickled garlic decreased.

• The Korean Journal of Pesticide Science
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• v.5 no.2
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• pp.26-32
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• 2001

[ ${\alpha},{\beta}$ ]-Unsaturated carboxamides 12 with trifluromethylated dihydro-1,4-dithiins were synthesized for the purpose of development of new agrochemical fungicide. Chlorination of trifluoromethylated ${\beta}$-ketoester 4 followed by tile reaction with 1,2-ethanedithiol gave intermediate 1,4-dithiane 9. Without purification of 9 substitution of hydroxy by chlorine followed by dehydrochlorination in the presence of triethylamine afforded trifluoromethylated dihydro-1,4-dithiin ethyl ester 7. Activation of the hydroxy of the carboxylic acid 10 obtained from the hydrolysis of 7 and then reacted with various amines gave the corresponding trifluoromethylated dihydro-1,4-dithiin carboxamides. Antifungal screening (in vivo) against typical plant diseases, Rice Blast, Rice Sheath Blight, Cucumber Gray Mold, Tomato Late Blight, Wheat Leaf Rust, and Barley Powdery Mildew of the synthesized compounds was carried out. As a result, most of the compounds shlowed weak antifungal activities and some compounds in which isopropyl group was substituted in meta of the phenyl showed antifungal activity (99%) at 250 ppm against the disease Wheat Leaf Rust.