• Archives of Pharmacal Research
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• 제26권1호
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• pp.9-14
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• 2003

For probing the importance of planarity of imidazolidinone motif of 4-phenyl-1-(benzenesulfonyl)imidazolidinones 1 for their cytotoxicity, 4-phenyl-2-(benzoyl)[1,2,5]thiadiazolidine-1,1-dioxide (2a), 4-phenyl-2-(p-toluoyl)[1,2,5]thiadiazolidine-1,1-dioxide (2b), 4-phenyl-2-(phenylcarbamoyl)[1,2,5]thiadiazolidine-1,1-dioxide (3a), and 4-phenyl-2-(p-tolylcarbamoyl)[1,2,5]thiadiazolidine-1,1-dioxide (3b) were prepared along with their regioisomers (5a, 5b, 9a, 9b) and their cytotoxicity were measured against human lung carcinoma (A549), human colon carcinoma (COLO205), human ovarian cancer (SK-OV-3), human leukemic cancer (K562), and murine colon adenocarcinoma (Colon26) cell lines in vitro. All compounds prepared do not show any activity against all five cancer cell lines unlike 1. Compounds 1 possess planarity of imidazolidinone, especially in sulfonylurea moiety ($-SO_2$NHCONH-). However compounds 2 and 3 have nonplanar 5-membered ring, [1,2,5]thiadiazolidine-1,1-dioxides. Such structural differentiation might result in the loss of activity. Therefore the inactivity of 2 and 3 could also be an indication for the necessity of planarity of imidazolidinone ring of 1 for their cytotoxic activity.

• 대한화학회지
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• 제39권10호
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• pp.834-836
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• 1995

• Bulletin of the Korean Chemical Society
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• 제13권1호
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• pp.8-9
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• 1992

• Archives of Pharmacal Research
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• 제25권4호
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• pp.421-427
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• 2002

For probing the importance of planarity of imidazolidinone motif of 4-phenyl-1-(N-acylindoline-5-sulfonyl)imidazolidinones 1 for their cytotoxicity, 4-phenyl-1-(N-acylindoline-5-sulfonyl)[1,2,5]thiadiazolidine-1,1-dioxides 2 were prepared and their cytotoxicity were measured against human lung carcinoma (A549), human colon carcinoma (COLO205), human ovarian cancer (SK-OV-3), human leukemic cancer (K562), and murine colon adenocarcinoma (Colon26) cell lines in vitro. Although only carbonyl moiety of imidazolidinone ring was replaced with sulfonyl group, compounds 2 do not show any activity against all five cancer cell lines unlike 1. Therefore the planarity of imidazolidinone ring of 1 should be an important factor for their cytotoxic activity.

• Bulletin of the Korean Chemical Society
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• 제17권3호
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• pp.290-291
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• 1996

• Bulletin of the Korean Chemical Society
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• 제13권4호
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• pp.357.1-357.1
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• 1992

• Archives of Pharmacal Research
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• 제14권1호
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• pp.78-80
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• 1991

Ten 1,2,4-thiadiazolidines were synthesized and screened for their anti-inflammatory and analgesic activities. Butyl isothiocyanate was used as a starting material. Several compounds showed significant anti-inflammatory and analgesic activities. The unsubstituted and o-methyl, p-acetoxy and o-chloro substituted compounds were found to be more potent anti-inflammatory and analgesic agents than the other compounds.

• 대한화학회지
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• 제40권7호
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• pp.526-530
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• 1996

3-Imino-1, 2, 5-thiadiazolidine 1, 1-dioxide와alkylamine 의 반응에 의하여 3-(N-alkylamino)-4, 5-dihydro-1, 2, 5-thiadiazole 1, 1-dioxide를 제조하였다. 이 헤테로고리 화합물의 주요 분광학적 성질과 X-선 결정학외절에 의한 분자구조를밝혔다. 3-(N-benzylamino)-4, 5-dihydro-4-(4'-methoxyphenyl)-1, 2, 5-thiadiazole 1, 1-dioxide의 단결정은 단사정계, 공간군은 $P2_1a$, $a=22.512(3)(1)\AA$, $b=9.831(2)\AA$, $c=7.194(4)\AA$, $\beta=96.65(2)$, 그리고 Z=4이다.

• 대한화학회지
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• 제39권7호
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• pp.564-571
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• 1995

NaOH 수용액에서 과산화수소로 2-thiobiuret를 산화성 고리화 반응시켜 5-amion-2H-1, 2, 4-thiadiazoline-3-one을 합성하였다. 이 화합물에 대한 토오토머화 현상을 IR, $^1H$ NMR, $^13C$ NMR 등의 분광학적인 방법으로 고찰하고 분자괘도함수에 의한 이론적 계산 결과와 비교 검토하였다. 이 결과 5-Amion-2H-1, 2, 4-thiadiazoline-3-one는 락팀형보다는 락탐형으로 존재한다. 알킬화 반응을 여러 염기로 DMF 용매와 이상용매계 $H_2O$-THF에서 시도한 결과 N-2 위치에서 알킬화 반응이 일어남을 알 수 있었다. 알킬화 반응은 할로켄화 알칸을 $Li_2CO_3$/DMF의 조건하에서 반응시켰을 때 가장 수율이 좋았다. N-2 위치에서 알킬화 반응 생성물의 확인은 IR, $^1H$ NMR과 $^13C$ NMR 등의 분광학적인 방법과 5-methyl-2-thiobiuret를 thiobiuret와 같이 산화성 고리화 반응을 통하여 5-amino-2-methyl-1,2,4-thiadiazolidine-3-one 표준 시료를 합성하여 알킬화 반응 생성물과 비교 확인하였다.