• Archives of Pharmacal Research
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• 제23권4호
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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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• 제11권1호
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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.

• 한국식품조리과학회지
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• 제11권2호
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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.

• 농약과학회지
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• 제5권2호
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• pp.26-32
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• 2001

새로운 농약살균제의 개발을 목적으로 trifluoromethyl기 dihydro-1,4-dithiin기 포함된 ${\alpha},{\beta}$-불포화 carboxamide 유도체 12를 합성하였다. trifluoromethylated ${\beta}$-ketoester 유도체 4를 염화한 다음 1,2-ethandithiol과 반응시켜 중간체 1,4-dithiane 유도체 9를 얻었다. 중간체 9의 정제없이 hydroxy기를 염소로 치환하여 생성된 중간체 8을 triethylamine 존재하에서 탈염화하여 trifluoromethyl기가 포함된 dihydro-1,4-dithiin ethyl ester 7을 합성하였다. Ester 7을 가수분해하여 생성된 carboxylic acid 10의 hydroxy를 염소로 치환하여 활성화한 다음 여러 가지 amine 유도체와 반응시켜 trifluoromethyl기가 포함된 dihydro-1,4-dithiin carboxamide 유도체 12를 합성하였다. 합성된 화합물을 대표적이 6종의 식물병원균, 벼 도열병원균, 벼 잎집무늬마름병원균, 오이 잿빛곰팡이병원균, 토마토 역병원균, 밀붉은녹병원균, 보리 흰가루병원균 등에 대한 항균력을 시험 (in vivo) 하였다. 그 결과, 대부분의 화합물이 미약한 항균을 나타냈다. 페닐기의 meta 위치에 isopropy기가 치환된 화합물 12h는 250 ppm에서 밀 붉은녹병원균에 대한 항균력 (99%)을 나타냈다.